Sometimes people email me and they are like “HEY WE ARE COMING TO CHICAGO” and I am like “AWESOME” and then I type them up an email of everything I think they should do. From now on, I’ll just send them here:
1) Green Mill is a bar (supposedly one of Al Capone’s speakeasies) that has live jazz and a very neat historical vibe. It is next to a 24-hour hot dog stand (yessss) and a used book store, and across the street from a good Ethiopian restaurant (in case, for some reason, you hate Chicago-style hotdogs and American-style freedom).
2) Newberry Library usually has good (small) exhibits open to the public, and sometimes public talks!
3) There’s loads of shopping, especially in Water Tower Place, and a good cafeteria-style restaurant downstairs (you go in, then up the escalator, then down the escalator to get there – it’s called Food Life).
4) If you like tall buildings, definitely go up in the John Hancock to the lounge and get a drink. A hot chocolate or adult beverage will run you $5-$10, but it’s better than the observation deck, which is $25+ with no chairs!
The John Hancock has better views of the city and Lake than Sears / Willis Tower. If you don’t like tall buildings, why are you coming to Chicago?
5) Navy Pier is fun to look around – there is a Ferris wheel (not the same one that was invented for the Chicago World’s Fair) and lots of touristy shops. You can also rent one of those four to eight person killer bike cars, which are always a good time.
6) Hyde Park is a great neighborhood to kick around in (made famous by the University of Chicago and the Obamas, perhaps?).
There are loads of used book shops full of treasures.
There’s a fun (and inexpensive) burger-and-milk-shake restaurant called the Medici.
The Museum of Science and Industry is GREAT! Very possible to spend all day there, and it’s just across the street (use the tunnel to cross!) from the Lake, so you can have a picnic on the beach!
There’s also the Robie House, designed by Frank Lloyd Wright, which has a fun, educational one-hour tour (and a mega-cool gift shop for the architecturally inclined).
7) Millennium Park is cool for ice skating in the winter, free concerts in the summer, and picnics whenever you’re feeling peckish. And you kind of have to take an obligatory Bean photo.
8) The Art Institute has student rates, so bring your ID if you have one.
9) On the Museum Campus there’s an aquarium, Field Museum of Natural History (very cool!), and planetarium. Also a nice place to have a picnic on the lake.
10) Pilsen is also a great neighborhood to explore, with delicious (and inexpensive!) bakeries (tres leche cake, yessss), great street art, and AMAZING Mexican food.
11) Of course, there’s Chicago deep dish pizza (Connie’s at 22nd and Archer is best, Pizzeria Uno’s is second best!).
12) Get the Chicago Mix from Garrett’s Popcorn (there are at least 5 locations downtown).
13) Lincoln Park Zoo is free, and near the lake.
14) The Chicago Architecture Foundation boat tour on the Chicago River is always always always excellent.
15) There are loads of paths for cycling, walking, and jogging around the lake, as well as lots of lovely beaches.
16) Shows! Go to shows! There are theaters all over the city as well as small theater companies and improv and general mad entertainment. There are comedy clubs and concerts all the time. Second City, Bye Bye Liver (recommended by SVS), local theater performances, dance, opera, music, orchestra, plays – Google the stuff out of that stuff.
17) I suppose Beverly / Morgan Park needs a plug:
Come on down to the Beverly Art Center for a show, class, or demonstration!
Eat a cheese dog at Janson’s (hasn’t been closed by the Health Department yet!).
Get a burger and shake at Topnotch on 95th Street.
Visit some of the cute old-timey bakeries in the area…
Okay, basically eat non-stop is what I am encouraging you to do. Yay, America.
18) Harold Washington Library is AWESOME. You can go all the way to the top floor and hang out in the atrium (quietly, or the security guards will bounce you), or stay there all day and read.
19) Andersonville area recommendations by KP:
Pizza: Pequod’s at Clybourn and Western, Ranalli’s, Calo
Watering holes: Simon’s, Hopleaf, Konak
Entertainment: Too Much Light Makes the Baby Go Blind
20) If, for some strange reason, you leave the city, Aurora, Illinois (about an hour away by Metra train), has great Mexican food and amazing bakeries (just down the street from the Metra Station).
21) If, for another strange reason, you find yourself in Evanston, Illinois:
There is an awesome (if slightly strange) secret rock and dinosaur bone museum in Dave’s Down to Earth Rock Shop on Main Street.
Joy Yee’s has good, not pricey pan-Asian cuisine.
Near Northwestern University there is a cool assemblage of painted rocks along the lake shore (FOR PICNICS).
There’s also a comic book shop and other stores that are fun to poke around in.
That is my recommended wine, dine, and book buying tour of Chicago and the surrounding area. But I forgot that I wrote this so I revised the list in 2014 with some other tips!