If you had asked me five years ago, I would never have guessed I would live in the Midwest - nor that I would have a great experience there and meet so many wonderful people. From the lovely, long summers, the beautiful lakefront, the stunning architecture, to the generous and genuine people, Chicago is an amazing city and it's not hard to admit that I truly miss it. It's been almost nine months now since I moved away, but people still frequently ask me what to do there and where to go. So I've put together this little guide to hopefully inspire you to visit this great city.
Fellow fair-weather friends, I do caution you: winter in Chicago is no joke! If you're like me, you won't have the right winter clothes to be comfortable if you're visiting from Southern California or similar climate. Either borrow some clothes or don't go from late November-March - just Google "polar vortex" if you're having second thoughts.
A lot changes in just a few months, so please feel free to add your own Chi-town tips in the comments! Enjoy!
SEE
Art Institute - It isn't quite the Met or the Louvre, but it is a must-do if you love art. My favorite exhibit is actually the sort of oddball Thorne Miniature Rooms, which are tons of period rooms in miniature, like one-room dollhouses. What a lot of guidebooks don't tell you is that the Art Institute is almost equally lovely outside and you can save your admission fee and instead wander the gardens, outdoor sculptures, and the fountain with the weird faces (which turns into a kids' wading pool basically on hot summer days).
Millennium Park and the Lakefront - From the Art Institute you can stroll down the beautiful BP Bridge to Millennium Park, which has the gorgeous Gehry-designed Pritzker Pavilion and Cloud Gate aka the Bean, among other lovelies. If you're feeling up for more walking, strolling down to Grant Park and by the Buckingham Fountain is a nice walk and the heading right over to the Lakefront is also nice and there is a path along the lake just past Lakeshore Drive.
Hyde Park/Museum of Science and Industry - I probably wouldn't have spent as much time down here if I didn't work there, but Hyde Park is a neat neighborhood and the University of Chicago campus is beautiful. Plus, the Museum of Science and Industry is my favorite Chicago museum!
Architecture River Cruise - We did this so many times I can practically recite it, but this cruise by the Chicago Architecture Foundation is well worth it and a great way to get acquainted to the city. Even if you aren't into architecture, you will learn so many fascinating details about the history of the city.
Frank Lloyd Wright Home and Studio - Again, I really wasn't that into architecture but a visit to Lloyd Wright's Oak Park home is well worth it for the history and I love this neighborhood.
Wrigley Field (game or tour) - Even if you aren't much of a baseball fan, this is one of the oldest ballparks in the country and steeped in fabulous traditions and history. If you can't make a game, the tour is great and you even get to go into the dugout.
Observation Deck?- I suppose if you've never been to a big city and up in a tall building, the Willis Tower (Sears Tower) is the tallest, but we usually would take people up in the Hancock Tower instead to the Signature Lounge where you can get an amazing view for just an overpriced drink rather than $30+ fee (tip - best view is from the women's bathroom, not kidding!)
EAT
This list was the hardest to put together and I tried to edit it down to the truly unique for Chicago. The trouble is there are tons of amazing places to eat and new places always opening. As you can see, I hate deep dish (although if you must, Lou Malnati's is my pick) and I also tended to really stick close to the River North neighborhood I used to live in.
GT Fish and Oyster - The oysters are off the chain (hello, Oyster Po'Boys), but the Lobster "Mac and Cheese" and Berkshire Pork Belly are also delicious. 531 N. Wells
Grahamwich - This Graham Elliott lunch-only place has the most amazing sandwiches and popcorn, plus yummy fries and gourmet sodas. 615 N. State.
Portillo's - While I don't like how it's become a chain, this is still the classic place to get a Chicago Italian beef (with hot and sweet peppers, dipped). 100 W. Ontario St.
Big and Little's - Did I mention you might leave with a heart attack? That old SNL skit was no joke! This place has the most delicious truffle fries and all kinds of yum fried foods. 860 N. Orleans
Citizen Bar - One of my favorites for brunch and also love the rooftop bar. 364 W. Erie
Piccolo Sogno - Delicious Italian, the best is the romantic patio out back. 464 N. Halsted
Medici Hyde Park - Okay, so the bakery part has amazing bagels, cookies, and other baked goods. Their burgers, sandwiches, and thin pizzas (Garbage Pizza, yum!) are crazy good, but their milkshakes and on tap Diet Dr. Pepper is the real reason I frequented this place. 1327 E. 57th St.
Beat Kitchen - For awhile we lived in walking distance of this place, but even after we moved I loved going over here and ordering off their unique record sleeve menus. 2100 W. Belmont Ave.
Taco Burrito King - This California girl needs her Mexican food fix, which is not easy in Chicago, but TBK is cheap and cheerful. Multiple locations but only been to one on 114 W. Chicago Ave.
Crisp - I hope my husband isn't mad I'm giving this away, because this is his all-time Chicago favorite. I think he might have starved when I went out of town if not for their Korean fried chicken wings. 2940 N. Broadway
Twin Anchors - We are a house divided when it comes to best ribs in Chicago (which also means maybe the world) but it's my list so my pick wins. The sauce is to die for. 1655 N. Sedgwick St.
DRINK
Drumbar - Rooftop bar at the Hotel Raffello, 201 E. Delaware Place
Pops for Champagne - I have yet to meet a glass of champagne I'd turn down...
Goose Island Brewery - sample some of the local brew, like 312 and Matilda (312 is an area code in Chicago), of course I have to mention it because they host USC Game Days too,
Cubby Bear - Despite its frat-boy vibe, Wrigleyville can be a fun experience and this classic bar often has live music
The Bedford - Love the atmosphere of this lounge where my favorite room looks like an old bank vault, complete with deposit boxes. 1612 W. Division
BE MERRY
The Hangge Uppe - A dive bar of a dance club, it's almost like a house party at this little gem. My favorite is watching on closed caption TV people dancing to different music who have no idea they are being broadcast in another room. Hilarious! 14 W. Elm
Old Town Art Fair- So Chicago's not a big club scene - the best things to do are just hanging out and drinking, preferably outside in the summer. There's a festival almost every week, and we've done a lot of them, but this is one of the biggest and best. Lots of drinking and food, galleries, gardens, music - in June each year. North Ave. area, Old Town Triangle
Castaways - I will probably get made fun of for this because it's really touristy and also kind of fratty at times, but I have spent some great afternoons sipping a beer and lounging by the railing on this fake beached "boat" right on Lake Michigan. So there! North Avenue Beach.
Lake Michigan - I had never been on such a big lake before I moved to Chicago - I actually thought you could see across it. Some annoying frat boys try to hype up the scene here at places like the Playpen to get girls to act like it's Lake Havasu or something (it's not), but when it's a hot and humid summer day, nothing beats going out on the Lake on a boat, any boat. Rent one from Montrose Harbor.
Second City - Even if you aren't a huge improv fan, you have to give props to the talented casts at this theater, who are often plucked and put on SNL. 1616 N. Wells.
SHOP
The Fudge Pot - My former boss acquainted me with this place, and oh boy, is it amazing and they can make anything out of chocolate. I love that it's family owned and my favorite is to pick out a custom box as a gift for someone, and one for myself to eat back in my hotel room. 1532 N. Wells
Veruca Salt - Maybe it's the name (loved that band!) but this is a cute, very edited selection of very wearable clothes and was near my old stomping grounds
Seminary Co-Op Bookstore - I've only been to the original one, which just moved to a new building on 5751 S. Woodlawn, but it's beautiful and I love to support independent bookstores.
Michigan Avenue - This is one of the things I miss the most. Shopping in NYC is amazing, but it's so spread out. I love how many great shops are all along Michigan Avenue (they have a Topshop!) and it's so easy to walk. I'd recommend starting at the bottom by the river and then working my way up, capped off by a drink at either the Drake Hotel or the Hancock Tower's Signature Lounge.
LOCAL TIPS
Neighborhoods - Chicago is one place where the neighborhood is everything, and each one has such a different feel and flavor. Choose a couple to just walk around for a few hours! Old Town is lovely, and I also love Bucktown, Lincoln Square, Roscoe Village, and Gold Coast.
Urban Oasis and Spa O - All the walking around you'll be doing will certainly leave you ready for a massage or a lovely manicure/pedicure (add a shoulder massage for $15). My fave massage place is Urban Oasis on 12 W. Maple Street. Spa O has a very convenient spot near Millennium/Grant Park at 1212 S. Michigan Ave.
High Tea at Intercontinental or Drake Hotel - I adore tea and we had a great experience at the Drake, a super gorgeous, classic Chicago hotel. They even gave us free seconds on our favorite tea sandwiches! The Intercontinental has an adorable service for grade school age kids where they bring a bear and some mini glasses full of desserts like gummy bears.
Getting around - unless you're going on a day trip, you can pretty much go anywhere via the El or taxi. I wouldn't recommend renting a car unless you want to leave town.
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