Things to do / see / eat in Chicago(land)

Sometimes people email me and they are like “HEY I AM GOING 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 this link because LAZINESS (aka “stream-lined efficiency”). [I wrote about Stuff To Do in Chicago before, but I forgot that I did that, so here’s my revised list.]

The name Chicago is derived from an Indigenous word that is widely considered to mean “smelly onion.” As a Settler (or non-Settler) visiting or living in the territory, you have an excellent opportunity to appreciate the colonial legacy of the grids, buildings, and environmental transformation all around you, as well as the present-day colonial implications of commerce, industry, transportation, and residency in the Chicagoland area and the broader North American context. Chicago was founded in 1833, so that leaves several hundred millennia unaccounted for in most (re)tellings of the area’s history.

Adapted from timelines of Canadian and Australian history via @InsideHistory on Twitter.

Adapted from timelines of Canadian and Australian history via @InsideHistory on Twitter.

With that in mind, regular readers know the drill. I like to eat food and read books. With those emphases in mind, here’s a partial and evolving list of thing to do / see / eat in Chicago for future visitors and / or Settlers and / or residents and / or other interested parties (all of which can be intersectional categories):

Myopic Books in Wicker Park is a great place to wander for hours and hours through precariously stacked shelves. It’s a treasure trove for book lovers / readers, and I found way too many while I was there (including some Doonesbury, Nature’s Metropolis, and some Brian Andreas anthologies, to list only the books nearest to me at the moment). (Thanks, CP!)

— If you, like me, have a greeting card / stationery problem, it’s definitely worth checking out the cute wares at Paper Doll (2027 West Division Street). (Thanks again, CP!)

— Likewise, Paperish Mess (1955 West Chicago Avenue) is an awesome place to poke around, pass some time, and pick up some Chicago map art, greeting cards, stationery, or paraphernalia.

— The Art Institute is a pretty rad museum. (If you bring a student ID, you get a discount! If you’re a Chicago resident, you get an even better discount.) It’s right beside Millennium Park, which generally has live music or ice skating or interactive sculptures or garden walks or other things to get up to whatever the weather.

— The Field Museum has very interesting exhibits. If you find yourself down in Hyde Park, there are great bookstores and a nice place for burgers / milkshakes called the Medici. Plus there’s a Frank Lloyd Wright house down there with a decent tour, and the University of Chicago campus is pretty fancy.

— The Newberry Library (60 West Walton), if I haven’t swooned about it enough in this blog, is super awesome. It’s a public research library! You can go use it! As long as you are over 16 with a photo ID! Everyone who works there is really helpful and kind, and their gift shop has SUPER ADORABLE / AWESOME books and greeting cards. They also have exhibits and events (and host weddings – man, missed opportunity!) and the time traveler in The Time Traveler’s Wife totally worked there (it’s fiction. shut up, I know that. don’t watch the movie – it’s the worst!).

— The John Hancock building is really tall. It has a lounge on the 95th floor, and an observation deck on the 96th floor. The observation deck costs lots of money and you don’t get a chair. The 95th floor lounge costs the price of a drink ($10ish, depending on what you order), and you get a chair so you can sit and look out the window at the awesome views of the city (if you find buildings and grids and lakes and boats aesthetically pleasing). Plus you can sit there as long as you like / order more drinks / tip well. Don’t forge to go to the lady’s room for the best view out the windows! (Not a joke.)

Harold Washington Library, in addition to being an awesome public repository for books, has a very nice top floor with a glass roof if you like to look at buildings / architecture.

— If you do zoos, the Lincoln Park zoo is free. They have a nice light exhibit around the winter holidays.


— The Chicago Architecture Foundation puts on a great river tour. They also have walking tours, which are likely just as good. (I’ve only been on the river tour like 30 times – I have yet to do a walking tour!)

— The Chicago Cultural Center offers free neighborhood tours hosted by authentic Chicagoans. Worth checking out if you want to get off the beaten tourist trail, although the Bean and all that is nice, too.


— There are lots and lots of theaters and performances in Chicago. The Shakespeare Theater on Navy Pier puts on great shows, but there are many, many more venues, including Second City, the Chicago Theater, the Beverly Arts Center. There’s opera, ballet, orchestral performances, singing, dancing, comedy – check the free weeklies for concerts, shows, stand up, or whatever strikes your fancy!

— The Hideout at 1354 West Wabansia Avenue is a place I had never even heard of before Bingo night with CP. It was really fun! They served hot dogs and beer – and we played Bingo. What’s not to like? It’s up-wind from the Chicago garbage truck lot, so we were in pretty good shape for Bingo night.

Too Much Light Makes the Baby Go Blind. They decide how much your ticket costs by rolling dice. I can’t even explain how much I love this show. Just go. My one regret in life is that I only started attending their performances recently when I could have been going for my entire life! (That’s it, that’s my one.) It is super-fantastic. Maybe the most fantastical thing ever. (I say this as a person who has attended a pirate and ninja wedding reception, which was pretty great, but this might have been better.)

— Caught a jazz performance at Kingston Mines on Halsted with JZ. Having only been there once, I would say it’s great! Also, showing them our student IDs got the cover charge waived. Woohoo, free music.

— You can find more amazing jazz over at the Green Mill (at 4802 North Broadway Avenue). They are open until 4 am! (That was really awesome when I lived next door. Now, it is still awesome, but my life is less conveniently located.)

— While you’re in the neighborhood, hit up the Tattoo Factory (at 4441 North Broadway Street). You know you want a Chicago flag tattoo. ALL the kids are doing it, and inevitably some of them are cool, so you, too, could be a cool kid with a Chicago flag tattoo.

— I swear one time I went line dancing at a cowboy bar in Chicago. I’ll have to get KP to remind me of the details on that, because it was pretty fun… But it’s worth wandering around to see what you can get up to on the streets of Chicago!

— For additional wanderings, you could check out Chicago’s underground Pedway (which will be useful, depending on the weather!). I knew about Montreal’s underground network of tunnels, but I first learned about Chicago’s Pedway from a December 2007 article in Chicago Magazine by Kim Conte. (There are apparently other secret tunnels, as well as some not-so-secret.)

Of course, on the topic of FOOD, there is much to say! I’ll leave you with:

— Bourgeois Pig Café has a quirky and delicious menu. (Thanks, JZ!) We sat outside under the trees in the shade at sunset and had a great chat, which I’m sure is influencing my review of the establishment. Also, the dude at the counter had on an awesome shirt and was very pleasant. Nice place to have a relaxed coffee / sandwich / intellectual banter session.

Oysy Sushi (50 East Grand Avenue) was recommended to us by some Marylanders in Southern California, but they were spot on. Lunch there was great!

— Hot Doug’s is apparently closing (sad), but you can still get a Chicago-style hot dog! Broadway Grill & Pizza (I did not know that place had a name until I Google’s it), just next door to the Green Mill, has hot dogs and they are open LATE. I know this because reasons.

— Finally went to the Berghoff on my last visit to the city. It was interesting to finally go inside the beer hall. Dinner was pretty good. I don’t think I need to go there again, but I’d recommend it if you like Chicago lore, because the backstory on that place is convoluted (like most things).

— There is so much pizza. I like… Fox’s (veggie is great!), Connie’s (deep dish), Waldo Cooney’s, Pizzeria Uno (because tourists), Giordano’s (deep dish)… You know, I am sure that there are blogs about this. All the pizza in Chicago is good, except for Pizza Hut and California Pizza Kitchen, which I am ruling out mainly because I have never eaten them.

— There are loads of neighborhood bakeries (Swedish Bakery, Beverly Bakery, any bakery anywhere in Pilsen), as well as doughnut shops (Glazed & Confused, Stan’s Donuts), if sweets are your thing.

— Beer! There is so much beer in this city. Go nuts with microbreweries if that’s your thing. Goose Island is particularly Chicago-y.


This list is strongly informed by a recent summer in Chicago. Additions will be added as I recall more. (And the overlap with the last list I made of Stuff To Do in Chicago tells you that my recommendations are so solid, I came up with some of them twice.)

I haven’t even started on comic book shops, thrift stores, 24-hour diners, Cubs games, Sox games, cross-town classics, boutiques, or general restaurant recommendations… but it’s a great city to visit and explore and critically analyze, so have fun! (More suggestions are always welcome.)

Kudos to lots of friends for several of the recommendations on this list! :-)

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