Chicago Visitor's Guide

Chicago!

Some of my favorite places, from a former tourist turned downtown girl. If I only had a few days in town, here would be my top Chicago trip picks: 

•  Chicago River Architecture Cruise.  Spring through late Fall only.  View the amazing architecture lining all three branches of the Chicago River. A truly memorable experience on a nice day. In order of my favorite companies:
• Shoreline Sightseeing.  These guys depart from Navy Pier, so you get a bit of a longer ride than the others since you have to enter through the lake and pass through the opening of the river.  Also, you can stand up on the boat and get a better vantage point for photos, but there will be a seat for you if you want to sit.
• Chicago Architecture Foundation.  Very nice tour.  You meet on the river, and you generally stay seated throughout the tour. This one is generally the priciest of the three. They don't oversell, so you'll have a seat.
• Wendella. Another reputable company with knowledgeable guides. The cheapest but not my favorite. Sometimes the boats are smaller and/or standing room only.  
• John Hancock Center's Signature Lounge.  Have a cocktail on the 96th floor of the John Hancock Center. The food is nothing to write home about it, and the drinks are overpriced, but for the cost of an $8 beer and tip, you can enjoy one of the most stunning views in the world. For a special treat, go before sunset and watch the city lights twinkle on. On a clear night, you can see for miles and can watch the planes line up on approach to Midway and O'Hare like pretty little strings of Christmas lights, with the Willis and Trump Towers in full view and the lights of the city far below you. Enter the side door on Chestnut Street (south side of building) for the quickest way in. Can be a bit of a line some evenings, but it's worth it. You may get lucky and get no line—it happens.  Don't miss the view from the ladies' room.  You can also buy tickets to visit the 94th floor sky lobby for a 360-degree view all around the tower. In the winter, there's a small ice rink up there—the highest in the world!
• Trump Terrace.  Late Spring through early Fall. Tied with the Signature Lounge for my favorite view in the city is this 16th-floor lounge located on one of the open-air setbacks on the side of Trump International Hotel & Tower.  A smartly selected menu of exotic cocktails and food provide a nice backdrop to a gorgeous view of the Chicago River, Wrigley Building and Tribune Tower in an elegant but trendy setting.  Go just for drinks or stay for a meal. Great for a date or with friends. My friend is the manager here, and he makes sure this place is a class act. It's on the pricey side, but you'll never forget that view, and this really feels like a special night out. For an extra treat, go Wednesday or Saturday nights, and you will be treated to a view of the fireworks from Navy Pier. Every Wednesday at 9:30 p.m. and Saturday at 10:15 p.m. Memorial Day through Labor Day weekend.  Just keep ordering--they get ticked if you're holding up the seating list. :)
• Willis Tower Skydeck.  Formerly Sears Tower.  Buy tickets to go up to the 103rd floor for another amazing view of Chicago and Lake Michigan.  This one is a little more of a formal "attraction" experience than the Hancock.  There's a short but interesting display on the way in, as well as a brief film on the tower's history and construction.  They have airport-like security, so you will go through a metal detector while your bag gets X-rayed, so leave the handcuffs in your hotel room. Be sure to get your photo taken in one of the Sky Ledge glass boxes, which extend out from the side of the building, 1,353 feet above the ground!
• Millennium Park.  See the city skyline reflect off The Bean (formally, Cloud Gate).  Some summer evenings, there are free concerts in the park.  In the winter, ice skate on the rink, which is turned into a large open-air restaurant in the summer.  Several companies offer Segway tours leaving from the area right around the park—these are so fun you forget how dorky you look. I once got to tear through the breezeways at Soldier Field on a Segway—Bears fans, be jealous. 
• Art Institute of Chicago.  A true world-class art museum that can absorb hours of your time.  Have your own Ferris Bueller afternoon here. Don't miss the Thorne Miniature Rooms on the lower level—I will never tire of these. Also located within the Art Institute are the famed American Gothic, Nighthawks, and A Sunday Afternoon on the Island of La Grande Jatte paintings, to name a few. 
• Field Museum.  Massive natural history museum.  A must-do for museum fans. Wear your walking shoes—it's huge! Spring for the touring exhibits--they cost extra, but they're always worth it.
• Magnificent Mile.  Stroll down the fabulous Michigan Avenue, home to stellar shopping and some amazing architectural gems.  Start at Oak Street and walk the two miles down to Buckingham Fountain in Grant Park.  Along the way, you'll pass three major shopping malls (900 N. Michigan, Water Tower Place, North Bridge), the famous Tribune Tower and Wrigley Buildings, the Chicago River, Millennium Park and the Art Institute.  Shopping includes everything from two Sephoras to Topshop to H&M, Bloomingdales and Nordstrom.  Visit mid-November to March to catch the Mag Mile magically lit up with one million holiday lights every evening.
• Catch a show.  Check event listings to see what's going on at the Goodman Theatre, Chicago Theatre, Cadillac Palace, Bank of America Theatre, Oriental Theatre and Lyric Opera, to name a few.
• Play ball!  Spring through late Fall only.  Catch the Cubs up north or the Sox down south.  For an all-you-can-eat/drink experience, look for Cubs rooftop tickets.  Several venues are lined up just across the street from the Cubs' outfield.  The views of the game happenings may not be as good as being in the stadium, but the party starts early.
• Shedd Aquarium.  Fun for all ages. There can be quite a wait for the dolphin show, which is not worth it if you've been to SeaWorld. Even without that, this place is good for hours of entertainment.
• Adler Planetarium.  Great for kids or science junkies.  If you've been to Kennedy Space Center or Space Center Houston, you could probably skip this, but it's an interesting and fun museum with a gorgeous view of the lake. Be sure to catch a show in one of the theaters.
• Museum of Science and Industry.  This one is a bit of a hike since it's a few miles south of downtown, but if you loved science class, don't miss it. There's a real 250-foot German U-boat inside the museum. 
• Christkindlmarket.  Late November through Christmas Eve.  Visit a real German Christmas market in downtown Chicago.  Enjoy some spiced wine and shop for Christmas gifts, foods, candies, handcrafted goods and traditional glass ornaments. I never miss the potato pancakes with applesauce and currywurst. Be sure to take some cheese strudel to go from the Helmut's tent.
• Oak Street Shopping.  This small area and its immediate environs are home to some pretty high-end shopping.  While not as bustling as it once was before the economic downturn, you can still find Hermes, Kate Spade, Vera Wang, Tods, Moncler and Barneys New York.  Don't miss Bravco, a beauty product junkie's dream. This is a tiny little shop selling both the commonplace and the most hard-to-find skincare, haircare and beauty products. Cash or check only.
• State Street Shopping.  Head south of the river on State Street for more affordable shopping. Here you'll find everything from H&M to Zara to Sephora to DSW to Nordstrom Rack to Macy's. Venture into the two-story Walgreens at State & Randolph.  I know what you're thinking—it's a friggin Walgreens. Trust me, I know what I'm saying. It'll blow your mind. Hit up the beauty area in the very back of the 2nd floor for great brands like Nuxe and Le Couvent des Minimes. For a sweet treat, stop in at Magnolia Bakery—whose banana pudding is even better than its cupcakes—or venture into the Block 37 shopping mall and head down to the Pedway level where you'll find Beard Papa's. Order a cream puff with the original crust and strawberry cream filling and thank me later.
• Riverwalk.  Stroll the south shore of the Chicago River on a concrete pathway, view the stunning skyscrapers up close and dine at a riverside restaurant.  My favorite riverside highlights:  the Leo Burnett Building, Trump International, 333 West Wacker, the Wrigley Building and the United Airlines Building.
• Second City.  Launching ground for the career's of some of the comedy greats of all time, Second City is a multi-theater comedy venue with intelligent and hilarious SNL-type improv skit comedy. Drink menu is reasonable.

Other Gems  

• Buckingham Fountain.  Grant Park.  See the famed fountain from the Married . . . with Children opening montage. Every hour on the hour, the center jet shoots up to 150 feet, and after dusk, the shows are choreographed with lights and music.
• Lakefront Trail.  Chicago has miles of paved sidewalk along the shores of Lake Michigan.  Walk, run or bike along the path from North Avenue Beach past Oak Street Beach and Ohio Street Beach down to the Museum Campus. Watch out for the duck poop!
• River North Gallery/Cathedral District.  River North is the neighborhood north of the Chicago River between Michigan Avenue and west over to the river's north branch.  There are numerous art, furniture and design galleries in the western reaches of this neighborhood.  Head east to see The Catholic Holy Name Cathedral and St. James Episcopal Cathedral.  The beautiful Archdiocese of Chicago is also located nearby, on Rush Street.  Stroll Erie Street between State and Rush Streets to see some beautiful architecture dating back to the 1800's, including the Driehaus Museum.
• The Rookery.  Architecture buffs, step into this building on South LaSalle to see its ornate construction details and gorgeous light-filled atrium.
• Santa Fe Building.  Another architectural gem.  Home to the Chicago Architecture Foundation and many world-renowned design firms.  Visit the gift shop to inquire about numerous architecture tours available.
• Macy's on State.  Formerly Marshall Field's, this is one of the oldest and grandest department stores in the country,  the building dating back to the late 1800's.  See the incredible Tiffany ceiling, made of over 1.6 million glass tiles.  During the holiday season, have a traditional pot pie under the massive Christmas tree in the 7th-floor Walnut Room.  For a less crowded experience, venture up to the 8th floor to take photos from above.
• Chicago Cultural Center.  Located just across from Millennium Park, the Chicago Cultural Center is a feast for the eyes. Carrara marble and intricate detail throughout, architecture fans will marvel at the stunning Healy and Millet glass dome as well as the largest Tiffany glass dome in the world.  Traveling art or historical exhibitions are hosted periodically. Admission is free.
• Navy Pier.  Outside it's a carnival with a mini-golf course, Ferris wheel, wave swing and an old-fashioned carousel. Inside it's a small mall with a big food court and an IMAX theater. Several restaurants are located around the perimeter. Enjoy the outdoor beer garden on a nice day and watch the boats on Lake Michigan.
• James R. Thompson Center.  Modern architecture fans, step inside this government office building on a weekday and just look up. It's like nothing you've ever seen.  Definitely worth a 10-minute stop if you're in the area.  Hands-down the coolest building I've ever taken a driver's license test in.
• Chicago Temple.  United Methodist Church located in the Loop. Another architectural gem in a city filled with them.  Step inside for a visual treat.  Check their website for tour information—the beautiful little "Chapel in the Sky" would be inspirational even to an atheist.
• Chicago Theatre.  Even if you're not seeing a show, this historic theater offers the Marquee Tour of its magnificent building.  Check their website for times. See the inside of this majestic theater, including the celebrity green room, the stairwell signatures of the greats, and even stand on stage where numerous legends have performed.
• Merz Apothecary.  If you can't make it to Lincoln Square to check out the full-sized store, the smaller store in the Palmer House Hilton is still well-worth a visit for beauty product junkies. You can find all sorts of German beauty goodies here (no, that's not an oxymoron), from German Nivea Cream to Lindesa Hand Cream to Elmex toothpaste.  A nice selection of candles, perfumes and more. While you're here, step into the hotel lobby—it's stunning.
• Afternoon Tea at The Drake Hotel.  Just off the Magnificent Mile, make a reservation to treat yourself to tea, finger sandwiches and scones in a relaxing and beautiful setting in one of the grandest hotels in Chicago.
• Millennium Station.  Entrance to this underground Metra commuter train station is off Randolph near the Chicago Cultural Center. Take a quick walk through it to see a visually arresting concourse that featured prominently in The Dark Knight.  This is one small portion of Chicago's Pedway—miles of labyrinthine underground corridors that pass beneath the Loop, keeping commuters sheltered from the elements.
• Comedians You Should Know.  For some cheap and hilarious entertainment, buy tickets for only $5 online or $10 at the door, but they're so good, they sell out often. Comedy shows are held in the spacious back room at Timothy O'Toole's Pub in Streeterville.  Good bar food menu.
• Movies in the Park.  Check out the Chicago Park District's website or Facebook page for free entertainment. In the summer and on through October, free movies are shown on big screens in parks around the city. Bring a blanket or towel and some snacks, and enjoy a free movie under the stars. Offerings range from John Hughes classics to real classics such as The Princess Bride to the newest DVD action releases. October offers up chills and thrills with horror and suspense movies. Movies generally go on at dusk. Look up the sunset time for that day, then try to arrive about 45 minutes prior to secure good seating. Seating goes fast, so don't be those jerks that stumble in, tiptoeing between blankets after the movie has already started. 
• Garrett's Popcorn.  Garrett's Friggin Popcorn, how I love thee. Get a small bag of the Chicago Mix (or "small mix").  This is 1/2 cheese popcorn and 1/2 caramel corn, only done loads better than those horrendous Christmas tins you've gotten in the past.  Multiple locations, and there are even a couple in O'Hare.  The small bag is pretty sizable.  I'll buy this and smuggle it into the movie theater, just because it's awesome.
• Vosges Haut-Chocolat.  Ordinarily I'd think paying 8 bucks for a chocolate bar was insane, but this place rocks my face off.  Multiple locations—including one in O'Hare—but I go to the one in the Shops at North Bridge on Michigan Avenue. If you like bacon and you like dark chocolate, try the Mo's Dark Bar. It will change your life. Don't be daunted by the price—you want to savor this square by square, rather than wolfing it down in one setting. All their varieties are great.  Pick up a sampler box as a gift—for yourself.

Where to Stay
Assuming you want to stay near as many of the above attractions as you can, here are my recommendations, in order:

1. River North.  The area bound by Chicago Ave to the north, the Chicago River to the south and west, and Michigan Ave to the east.  My hood.  I'd say I'm biased, but I picked it for a reason.  The CTA Red Line (subway/el) train runs right up State Street, underground.  This is a convenient three-block (7-minute) walk to Michigan Avenue, and in the heart of loads of nightlife and restaurants.  You can walk to the river or even the lake in minutes.  Even at 2am, this area is well-populated.
2. Mag Mile/Streeterville/Gold Coast.  From Michigan Avenue east of River North to the shores of Lake Michigan.  It's a bit longer of a walk to the train, but you could be very close to some tony shopping and fine dining.  Streeterville is directly east of River North, while the Gold Coast is just north of Streeterville. These areas tend to be quieter and a bit deserted at night unless you're very close to Michigan Avenue.
3. The Loop.  This is the area south of River North, just south of the Chicago River.  Known both as the financial district and theater district, the Loop is bustling during weekdays but more desolate at night and on weekends once you're off State Street or Michigan Avenue.  You're very close to the theatres, State Street shopping, Millennium and Grant Parks, as well as the Museum Campus.  Numerous train lines run through the Loop, for commuters coming into work. 

 Getting Around  

• Driving in the city. If you're staying downtown and plan to stick with the city (not venture into the burbs), you don't need a car. Downtown parking can be hilariously expensive, from around $35 per night in city parking garages to nearly $50 a night at some hotels. Street lots or metered spots can be cheaper options, but possibly less convenient. The CTA (Chicago Transit Authority) and cabs can get you most anywhere, and probably cheaper.
• Navigating.  If you've got an Android smartphone, you're in luck.  Just enter the address of your destination, and Google Maps is very reliable with giving you options for the bus and/or train lines—just select the "Bus" icon, which will give you any public transport option.  I think iPhones do this as well.  Download the RedEye app—named for the Chicago Tribune's daily pop culture paper—for accurate bus and train arrivals tracking. Just be sly about using your phone at a bus stop or train platform—thieves here love to swipe phones and run.
• Public Transportation.  CTA bus trips are $2 each way, cash or transit card. Credit cards not accepted.  CTA train trips are $2.25 each way, transit cards only. Transfers are $0.25, whether bus or train.  If you'll be around for more than a couple of days, some or the larger train stations (e.g., the Red Line's Chicago station) have automated machines that will sell you a multi-day unlimited-fare pass that you can use on CTA trains or buses.  Some Jewel-Osco grocery stores also sell these at the customer service desk—the one at Grand and Ohio does. If you plan to take the Metra to the suburbs, please note that's a separate system with separate ticketing. Purchase those tickets online well ahead of time for mail delivery or at the station before your trip.
• Cabbing it.  Cabs are everywhere, but unlike NYC, they're not all yellow and they're not all cars, so just hold your arm up and hope for the best. If you're downtown, it should be pretty quick to catch one just by stepping out onto the street. If you're in the burbs, you may need to call one. You may end up in a white SUV or a maroon Scion, but it's all good. Cabs from Midway to downtown run about $35, including tip.  From O'Hare to downtown, you're looking at around $45-50 including tip. All Chicago cabbies are required by law to accept credit cards, so on the rare occasion that they grouse about it, remind them of that fact.  Some will happily accept them and even have a Blink terminal in the back for tapping your chip-encoded credit card.
• Getting downtown on the train from the airports.  Luckily, if you don't want to spring for a cab and need to get downtown from one of the airports, you're in luck.  If you have two hours to blow, Go Airport Express offers a multi-stop shuttle van service for roughly $30.  If you have about 30 minutes to an hour to blow and only want to spend a couple of bucks, here's how you do that with luggage (stations listed have escalators and/or elevators):
• O'Hare to downtown:  Follow signs in the airport terminal for Trains to City—this is the Blue Line.  A quick 10-minute walk in the terminal. Buy a transit card once you're near the trains and load it with at least $2.50. This train is only going one way—O'Hare is the termination point.  Hop on the train and settle in.  The train will get more crowded the closer you get to the city, so tuck your bag away as best as possible. The Blue Line will pass right through the downtown Loop.  If your hotel is near one of the Blue Line stops, great—should take you about 45 minutes to one hour.  If you need an elevator, please note not all stations have them—check the maps inside the train car. Those stations with a Handicapped symbol beside them (e.g., Clark/Lake, Jackson) will. Those without may only provide an escalator up, or worse, only stairs. The Washington Blue Line stop is centrally located in the Loop and has an escalator up (but not down).  I should note for the non-city folk: the elevators will smell like pee. The price you pay for convenience is being surrounded by the smell of urinal for 15-30 seconds. Has been this way in any city I've been to with subway elevators. Accept it, and take your shoes off in your hotel room.  Like many of the hotels, my place is near one of the Red Line stops, but there are a couple of easy ways to transfer.  
• If you only need an escalator.  To transfer, get off the Blue Line at Washington, follow signs toward the Randolph end of the platform, take the escalator up and follow signs to the Red Line.  There, it's just a quick 100-yard walk through the shiny new Block 37 Pedway to the Red Line.  This will be the Red Line's Lake station. Use your transit card, and head toward Howard if you're going north, or 95th/Dan Ryan if you're headed south. The Red Line's Lake, Chicago and Grand stations all have elevators up to street level. Note: When you return, there's no escalator down at the Blue Line station, so you're either walking your bags down the stairs, or try the reverse of the next option:
• If you need an elevator.  This option takes you a bit further south, will add a few stops to your jaunt, but it's elevators all the way at every level. Take the Blue Line to Jackson. Once you get off the train, don't take the stairs down to the Red Line--look toward the end of the platform for the elevator. Take that, then follow signs to the Red Line. You'll walk about 100 yards down a long corridor, then you'll arrive at the Red Line's Jackson station. Use your transit card, then you get past the turnstile, don't go straight ahead toward the stairs--look around the corner to your left--there's an elevator down the corridor that'll take you down to the platform.  Head toward Howard if you're going north, or 95th/Dan Ryan if you're headed south. The Red Line's Lake, Chicago and Grand stations all have elevators up to street level. 
• Midway to downtown:   35 minutes door-to-door to my place. Follow signs in the airport terminal for Trains to City—this is the Orange Line.  A quick 10-minute walk in the terminal. Buy a transit card once you're near the trains and load it with at least $2.25. This train is only going one way—Midway is the termination point.  Hop on the train and settle in. The Orange Line will pass right through the Loop.  If your hotel is near one of the Orange Line stops, great.  If it's off the Red Line, transferring is easy.  To transfer, get off the Orange Line at Roosevelt (this is before you get to the Loop) and follow signs to the Red Line. You don't even need to swipe your card again—this transfer is free—and head toward Howard if you're going north, or 95th/Dan Ryan if you're headed south. 
• General Note:  If you have a carry-on roller bag, after you swipe your transit card at the turnstile, push the bag under the bars, then follow it through.  If you have a large bag and/or stroller, it's best to get out or transfer at one of the stations with a Handicapped symbol next to it on the map (Jackson, Grand, Chicago). Those will all have a button-activated swinging door so you and your luggage/stroller can easily walk through.

Eat!

My favorite thing to do in this city.  You can go broke and/or get fat here, but you will enjoy every second of it.  Here are some of my favorite haunts in the downtown area, in no particular order.  Check out Yelp for reviews, Foursquare for ordering tips and the OpenTable app for reservations. I have plenty of faves outside the downtown area, so PM me if you need a recommendation.

Downtown 

• Gilt Bar.  Terrific restaurant and bar with a speakeasy feel.  Stellar reviews.  Everything here is amazing.  Seriously, bring stretchy pants and eat (and drink) everything. Head downstairs to find the darkly lit Curio lounge with cozy sofas underneath the restaurant. Great date spot.
• Quartino.  Italian tapas in the heart of River North.  Not the classical red-sauce-laden Italian fare that you're thinking of, this bustling eatery boasts some of the most delicious, melt-in-your-mouth pork shoulder and tortellini that I've ever had.  More classically Northern Italian fare, with an affordable selection of small, hand-tossed pizzas, This place is hopping 7 days a week. Nice bar area.  Outdoor patio dining available in nice weather with a very nice ambience that so many outdoor patios are lacking.
• Lou Malnati's.  Multiple locations, but my favorite is on North State Street in the Gold Coast.  THE Chicago deep-dish pizza.  Get Chicago Classic--buttercrust goodness filled with delectable slabs of sausage. You can skip the salads (just OK), but the breadsticks are amazeballs. They do carbs here, and they do them well. If you're wondering,  Gino's and Pizzeria Uno/Due just aren't as good--and Pequod's and Pizano's are just outright bad. Giordano's is good, but it's stuffed-crust pizza—not classic Chicago deep dish—if that's what you're after.
• Purple Pig.  Amazingly delicious pork-based menu on the Mag Mile. Very small eatery with an award-winning menu, including the best bone marrow I've ever had. Prepare to make friends with neighboring diners—this place can get crowded.  Outdoor patio dining available in nice weather.
• The Gage.  Located on South Michigan Avenue near Millennium Park.  Looks like a fine dining establishment, but casual wear is fine. Great wine and beer list with interesting items on the menu like elk ragout poutine. Surprisingly affordable. Be sure to visit the ladies' room, if for no other reason than to experience their lovely Penhaligon's Quercus hand soap and lotion.  Outdoor patio dining available in nice weather.
• India House.  My Indian buddy says this is the best Indian in the city.  Massive menu, so there's something for everyone.  Boasts the tastiest meal I've ever had in Chicago—Tandoori chicken, saffron rice and naan bread with a cold King Fisher beer.  Perfection. Service can be slow, so settle in and relax.
• NoMI.  Located in the Park Hyatt overlooking the Water Tower. Stop into the NoMI Lounge for a casual glass of wine in a refined setting.  Small-but-tantalizing menu for light bites or a full-blown dinner—everything from cheeses and olives to bone marrow and steak. Trendy but surprisingly friendly atmosphere. Or make reservations at the adjacent NoMI Kitchen restaurant for the full-fledged dining experience.  
• Pastoral.  The best sandwiches I've ever put in my mouth. Located in the Loop, Pastoral is a small shop that sells wines, charcuterie and cheeses in a rustic setting, and they also have a hell of a gourmet sandwich menu. My favorites are the Blue Pig & Fig, Le Canard and the Sandwich Campagne. When I actually drove in this city, I once drove around for half an hour looking for parking to get to this place and ended up parking half a mile away and walking to get food here. It's that good. Not much seating, but since so many do carryout, I'm usually lucky.
• Al's #1 Italian Beef.  Multiple locations, but my favorite is on Ontario.  Italian beef sandwiches are what they do here—another Chicago specialty that's perhaps not as well-known as deep-dish pizza or the Chicago dog, but just as delicious.  This is a divey little place that serves up a behemoth of taste.  Get the #5 combo for an Italian beef with fries and a drink.  Do yourself a favor and get the sandwich dipped and with hot peppers for a bit of a kick. Without either, it's just bland. With both, it's a foodgasm.  What this fast-food hole in the wall lacks in ambience, it makes up for in classic Chicago tastes.
• Portillo's.  Pronounce the L's the gringo way, like Amarillo. If you want some cheap eats and/or are dining with kids or folks who can't agree on what they want to eat, head to Portillo's at Clark and Ontario. They make a fine Chicago dog, but their specialty salads and chili dogs are also forces to be reckoned with. They have a varied menu, with everything from typical street fare to fettucini carbonara.  Don't miss the chocolate cake. You may even catch the ladies behind the counter singing out your order number. 1920's street fair ambience.
• Wildberry.  Drool-worthy brunch just north of Millennium Park.  Everything here is incredible. Good coffee variety. Expect a bit of a wait on weekends, but there's a nice patio out front overlooking the park to kill time with your pager.
• ZED 451.  Also located in River North is a unique restaurant that you won't soon forget.  When it's warm out, check out the rooftop bar.  When it's cold, nestle by the fireplace.  Year-round, enjoy its unique harvest table menu of fresh delights, or upgrade to the all-you-can-eat chef's selection of carved meats. Everything is magnificent. Nice wine list. The bar area makes a great blueberry mojito.
• D4 Irish Pub.  If you're looking for a nice pub, this is a favorite of my friends.  Cozy fireplace in the winter.  Check out the beer flights and the lobster mac & cheese. Our go-to place to grab a bite before catching a movie at the AMC River East 21 Theatre nearby.
• Gyu-Kaku.  Japanese BBQ with a Korean flair.  Dine in the restaurant for the full menu or grab a seat in the small upstairs bar area for cheap and delicious happy hour menu every day. Everything on the upstairs happy hour menu is great. We have literally eaten them all.  My industry friends' cheap little secret. 
• Slurping Turtle.  My favorite place to go for sashimi and noodles. Love their lunch bento boxes.  They have everything from pork belly to duck fat fried chicken. 
• M Burger. If you're craving a quick bite and want a delicious burger—or grilled chicken sandwich—head into this tiny little high-quality fast food joint. Get the M Burger and fries.  They often have seasonal milkshake flavors not listed on the menu, so be sure to ask.
• Fleming's Prime Steakhouse.  The best filet and the best service I've had anywhere in the world.  They really bend over backwards on service here, and this place won't break the bank quite as hard as some of the other local steakhouses.  For the best happy hour I've found in the city, head to the bar area for their 5 for $6 till 7 menu. Five appetizers, five wines, five cocktails for only $6 each until 7pm.  They don't even charge extra for premium vodka.
• Fogo de Chao.  Brazilian churrascaria / meat bacchanalia.  You know the deal. Stretchy pants.  Don't get duped and fill up on the salad bar first.
• Tavernita.  Brand-new eatery on Erie and LaSalle.  This place has been packed every day since its opening.  Excellent Spanish pintxos (tapas) and inventive cocktails.  For a quick snack, drop into Barcito—its attached corner bar—and try the Serrano ham and tortilla española on crusty bread. 
• Joe's Seafood, Prime Steak and Stone Crab.  All the seafood under the sun.  The reviews speak for themselves.  Whether you're in the mood for steak or fresh seafood, this place delivers. Solid wine list.
• Shaw's Crab House.  An equally excellent seafood restaurant.  Very fresh seafood.  Surprisingly sizable sushi menu, terrific in-season crab selection and the freshest oysters in the Midwest. Check the dates for the annual Lobster Fest for great lobster specials, held every summer.
• Pops for Champagne.  For from being only a champagne bar, this lively spot serves up a nice wine list and a great little menu for light bites.  Great for happy hour or just a leisurely stop. Venture downstairs to Watershed for some more unique cocktails, including everything from rye-based concoctions to absinthe.
• Sushi Samba.  Sushi with a Brazilian twist.  This place can get packed.  Definitely a see-and-be-seen place, but the sushi is legit.
• Friends Sushi.  Far from being a big, loud, sceney place, this is a very small restaurant with a quiet ambience that serves up consistently great sushi. Forget the California roll; you'll find some more exotic pickings on this menu.
• L'Appetito.  For quick and cheap bites.  Multiple locations—I go to the ones at the base of the Hancock Center and at Huron & Wabash.  This is a little, inexpensive Italian deli with pastries, panini, olives, cheeses, foreign sodas, coffee and made-to-order sandwiches. Grab an Italian sandwich and a San Pellegrino Aranciata.  The Hancock Center location has a very big indoor seating, while the Huron location has just a little bit of seating.
• Zapatista.  Authentic Mexican in the South Loop with nearly every region of Mexico represented on the menu.  This place has even won over my Tex-Mex-hating self.  Get a Bloody Mary with a mini-Corona on the side.
• More Cupcakes.  Located in the Gold Coast, this small cupcake shop serves up the tried & true, such as red velvet, along with more exotic flavors like mango & cilantro and bacon bacon bacon.  If you're a Sprinkles Cupcakes fan, there's also one of those nearby in the Gold Coast.
• Hendrickx Belgian Bread Crafter.  Small-but-amazing European bakery in the Gold Coast.  Their chocolate croissants are heavenly. Lovely bread and pastry selection with a small sandwich menu.  Get there early, as they tend to sell out of the more popular items.
• Soupbox.  Soupbox, how could I forget you? This is nothing fancy, just a tiny little place tucked away on Chicago Avenue, a quick walk from the Chicago Red Line station or the Water Tower. Good selection of delectable soups--and my favorite, the mouthwatering sourdough breadbowl--to warm you from the inside on a cold winter day. Definite comfort food.
• Farmhouse Chicago.  Located just outside the Chicago Brown Line stop, this craft tavern/restaurant isn't in the most scenic area, but it's a wonderful little gem with a friendly staff.  A nice selection of area craft beers and a menu filled with sustainable/local fare with inventive flavors, the menu will satisfy the discerning palate with a conscience. I had the best mussels I've ever eaten in my life here, and the Wisconsin cheese curds appetizer is a don't-miss. Far from just being a trendy, feel-good place, this restaurant really delivers a satisfying dining experience.
• GT Fish & Oyster.  Where to go in River North for really great seafood. Everything from Pemaquid oysters to Alaskan halibut.
• LUXBAR.  Popular Gold Coast eatery with a nice outdoor patio. Although they have a good brunch menu, I prefer their dinner fare for a late lunch on a Sunday. Best truffle fries, and the lobster & filet mignon sliders and King Crab bisque are ridiculously sinful.

Further Out

• Piece.  If you venture outside downtown and make it over to Bucktown/Wicker Park, this is one of my absolute favorite places in the city. Expect to wait a good 45 minutes for a table, but you can amuse yourself at the bar with some unique and delicious beers brewed in-house. You won't find Chicago deep dish here. The pizza here is more of the hand-tossed rustic variety, and you can order your own custom pizza. My sausage-spinach white pizza may never be topped. :)
• Revolution Brewing Company.  You might have noticed a pattern here, but brewery/restaurant combinations are quite popular in Chicago.  This Logan Square location is legit, and their brunch menu serves up everything from French Toast to Cherry Porter Pancakes. Their Black Power stout is one of the favorite beers I've ever had. How could you not love a place with bacon fat popcorn on the menu? That's right. Bacon. Fat. Popcorn. It's glorious.
• Rocks Lincoln Park. Thankfully not a TV-filled sports bar like so many venues in Lincoln Park, this restaurant/bar is located in a charming neigborhood area and has a nice, relaxed ambience. The best fish & chips I've had in the city.
• The Violet Hour.  An unmarked wooden doorway hides one of the best lounge experiences in Wicker Park.  Violet Hour is all low lighting and private booths and heavy drapes. No cell phone calls, no Grey Goose, no douchiness. Just craft cocktails, a knowledgeable staff and a solid menu of delectable bites. Go right after work to avoid a wait. Just look it up on Google Maps Street View first so you know where you're going.
• Hot Doug's. Waited over three years to make the pilgrimage to this much-heralded meat emporium. Vegetarians probably wouldn't find the interminable wait worth it, as there's little fare here for them.  For you meat-a-tarians, press on. Located in Avondale, don't expect there to be much of a neighborhood scene to entertain you as you endure up to a two-hour wait outside on the sidewalk, but once you're in, a gastonomic adventure awaits.  Enjoy the wondrous taste of duck fat fries on Fridays and Saturdays. Foodies may wish to bypass the standard menu of dogs named for celebrities and focus on the specials menu, which includes the likes of the melt-in-your-mouth, eye-rollingly good Foie Gras and Sauternes Duck Sausage with Truffle Aioli, Foie Gras Mousse and Fleur de Sel. Cash only.
• Cafe Ba Ba Reeba.  A quick walk from the Brown or Red Lines, this bustling Lincoln Park restaurant has a nice outdoor patio and a menu full of delicious Spanish tapas. Every bite of every dish is filled with flavor. The sangria doesn't disappoint. 
• The Bedford. This place is home to one of the best burgers I've ever had. So rich, it's served in a bank vault. So rich, they should make you sign a prenup before you order it.  The Bedford Burger is graced with bacon, blue cheese jam, gruyere (my personal fave) and a fried egg. Far from being mere filler, the thin-cut fries are amazing. Otherwise, a smartly selected menu with interesting touches awaits at this Wicker Park eatery.
• More to come, the more I eat! If you want a specific rec, just ask, although I probably shy away from the frou-frou, $200-a-plate, jacket-required places in favor of the trendier or divey-but-delicious joints.

Rooftop Bars

With such hard winters, drinking in the sun—or under the stars—is a popular pastime here when the weather warms up.  Here are a few of my favorites. Check the hours, as rooftop bars may be subject to noise ordinances and restricted hours. 

• Trump Terrace.  Stunning views with the gleaming Trump monolith rising into the Chicago sky above you. Pricey but every visit is memorable. 
• NoMI Garden.  Gorgeous rooftop patio at NoMI at the Park Hyatt, next to the beautiful Peninsula Hotel.
• ZED 451.  Smallish rooftop bar at a terrific restaurant.  Serene vibe.  Have drinks on the roof then head down for dinner.
• Rock Bottom Brewery.  Spacious rooftop bar on State Street. Young professionals party vibe atmosphere. Great beer selection.
• ROOF at The Wit.   Trendy drinks under the stars in the heart of downtown.  Get there early on a weekend to have any hope of not waiting in line. Also busy around happy hour on weekdays.  They've added a retractable roof in the last couple of years, so even if the weather is brutal outside, you can stay warm and have an incredible view.
• Epic.  Cocktails and bites in River North.  Relaxing happy hour or buzzing Saturday night—your pick.
• Vertigo.  Sky lounge atop the sleek Dana Hotel with a sizable indoor area. Party atmosphere.

Hotels I Like
I stayed at a number of these before I moved here, but in general if you stick to the areas I listed above and the web reviews are good, you can't go wrong.

• The Drake Hotel.  The grandest of the grand. Princess Diana stayed here. Nuff said. Near Oak Street shopping. 
• Westin Michigan Avenue.  Ask for a room with a view of the Hancock Center. Great location on the Mag Mile.  Friendly service.
• Hilton Chicago.  One of the most stunning lobbies I have ever seen.  Near Grant Park in the Loop, so it's close to the museums but out of the nightlife fray, if that's your desire.  The area around it can be sketchy, so bear that in mind if you're taking public transportation or parking yourself in a remote lot. Refined vibe.
• W Lakeshore.  As with everything right on Lakeshore Drive, a bit of a daily hike to and from the train, but the city views from this hotel are staggering.  Even better than the lake views.  Hip vibe.
• Hotel Sax.  Visiting friends have stayed here on business.  Bit of a funky, bordello vibe.  I love the rooms.  Right by the river and House of Blues. Crimson Lounge downstairs is trendy.
• InterContinental.  In the heart of the Mag Mile. A few friends have stayed here. There's not a better location in town.
• Trump International.  Unbeatable views of the cityscape and river.  A few lucky friends stay here on business. Another amazing location.
• Embassy Suites.  My company puts people up here.  Great location in the thick of the River North nightlife.  The only downside is that there's a smoker's area right outside the front door.
• The Peninsula. Another amazing location in the heart of the Mag Mile. A couple of my friends are managers here, and they work their butts off.  Every restaurant here is great.  Would be my pick if money were no object.
• Park Hyatt.  Home to the terrific NoMI, this is one of the go-to locations for celebs. Overlooks the Water Tower and is just steps from Michigan Avenue.  Very courteous staff.

 See you soon!