we embarked on our recent trip to chicago with an excessively long list of restaurants and bars that we wanted to try starred on google maps. we knew we couldn’t get to everything in 4.5 days, but we sure did our best, and ended up with a slightly shorter yet still long list of places we can now report back as worth going to. i’ve organized the list by neighborhood, since we mainly hung out in four main areas: logan square, wicker park, west loop, and river north. a few places we visited didn’t quite fall into one of these neighborhoods, so you’ll see them at the end in a miscellaneous section.
we stayed in the logan square neighborhood at this airbnb apartment and absolutely loved it. i loved staying outside of downtown where it was quieter and with more of a neighborhood feel, but i still felt like we were “in” the city and the loop, etc. was only a short ride away on the blue line train. the apartment was just perfect for us – a clean, bright studio with tons of natural light, a comfy bed, and a very responsive and accommodating host. we’ve had such good luck with airbnb so far in several cities, but katherine’s apartment was quite the gem.
without further adieu, our complete list of what to eat, drink, and do in the windy city…
longman & eagle | 2657 n kedzie avenue
this place is a trifecta of awesomeness: restaurant, bar, and hotel. we just grabbed a drink here one night, so i can’t speak for the food (though the menu looks great), but the cocktails were delicious and very inventive. L&E is very classy but still manages to have that neighborhood feel and the bartenders were extremely friendly. there’s also a more casual bar (OSB @ L&E) in the back that has a smaller cocktail selection and serves bar snacks – a cool vibe there, too. we loved our airbnb, but next time would love to stay in one of the rooms here.
90 miles cuban cafe | 2540 w armitage avenue
great little cuban joint with lots of character that came recommended to us by several friends. we both got sandwiches here – kevin the bistec del palomilla and me the medianoche – and we really liked both, and they came with delicious plantain chips. next time i’d skip the tostones (not a ton of flavor) and try some empanadas instead.
analogue | 2523 n milwaukee avenue
didn’t know much about this bar other than that it was close to our apartment, so we stopped in for a post-dinner drink one night. pretty small space, very busy (and dark), serving craft cocktails and cajun food. it was a little…”hipstery,” but we enjoyed ourselves nonetheless. the green river negroni was excellent (salted watermelon!), and our bartender was awesome and gave us some recommendations of other places to visit in the city; always a nice touch.
revolution brewing | 2323 n milwaukee avenue
one of chicago’s bigger breweries in addition to goose island. this location is a full-service restaurant and bar, but we just sat at the bar and tried taster sizes of a bunch of the beers. they have a ton on tap at any given time, so plenty of styles to please everyone, plus they carry bottles from a bunch of other local breweries. didn’t have time on this trip, but hoping to take a tour next time.
the radler | 2375 n milwaukee avenue
german-focused restaurant and beer hall. we sat at the bar and tried their signature drink – the radler – which is beer + fruit soda (kevin had blood orange, and i had grapefruit), with the optional addition of a shot of gin, vodka, malort (yes please). i’ve heard their pretzels are amazing – had we not just had dinner, we definitely would have tried one. next time!
intelligentsia coffee | 2642 n milwaukee avenue
there are several locations throughout the city, but we really enjoyed this one. it’s newer, i believe, with bar-like seating and counter service. the coffee here is excellent; i always try to order an espresso or macchiato at places like this so i can really taste the quality. they’ve also hopped on board the toast trend – you can order crumpets with any number of delicious toppings; we really liked the askinosie chocolate spread and the cherry jam.
gaslight coffee roasters | 2385 n milwaukee avenue
this place came recommended to us by the barista at our local coffee shop here in omaha. a super pretty space that would be a great place to hunker down for a couple hours or work remotely. great cappuccinos and lots of pastry options, including awesome savory croissants!
trenchermen | 2039 w north avenue
awesome brunch spot in an old turkish bath house. they’ve preserved a lot of the character of the old space, which is neat. they have a prix fixe brunch option where you can get a pastry, a main dish, and a side for $20 – i definitely recommend going that route so you can try a bit of everything. great bloody mary’s as well!
big star | 1531 n damen avenue
an absolute must for late-night drunk food. delicious, cheap tacos and $1 miller high lifes. need i say more? (warning: cash only)
piece brewery & pizzeria | 1927 w north avenue
the place to get pizza in chicago if you don’t really like deep dish. this is a thinner, sweeter crust with a build-your-own-pizza concept, and the topping options are endless (and include mashed potatoes…yes, we went there). even on a sunday night, it was packed and the service was kinda slow, but delicious pizza. bonus: they brew their own beer on site as well.
caffe streets | 1750 w division street
another coffee shop recommended by our barista – a neat (though pretty small) place with really cool seating and a friendly, neighborhood vibe. we got macchiatos here one morning while waiting for our brunch reservations down the street – very good!
NEAR WEST SIDE / WEST LOOP
girl & the goat | 809 w randolph street
oh, where to begin? we made reservations here in september before we were even for sure about taking this trip. we’ve long idolized stephanie izard since her win on top chef, and have been wanting to eat here forever. i was afraid that since we’d built it up so much, it might not meet our expectations, but i’m happy to say that it met and far exceeded them, and was one of the best dining experiences of our lives. the whole menu is shareable small plates (aka the best concept ever), so we ordered bread, oysters, cauliflower, shishito peppers, scallops, and goat loin to share, and literally loved all of it, particularly the goat. for dessert, we had a small cheese plate and the apple buckle – both wonderful as well. the service was excellent – they explain the concept well and course everything out for you, which is fun and really makes it feel more like an evening out versus just dinner. highly recommend, but make sure you get reservations way in advance (or be prepared to wait).
little goat | 820 w randolph street
the sister restaurant of girl & the goat, little goat is just down the street and offers inventive twists on diner-style food, such as waffles with peanut butter butter and bacon maple syrup or goat hot dogs with maple barbecue sauce. very busy on the weekends for both brunch and dinner, but we had no problem getting a table on a monday morning. amazing service with the same casual, comfortable vibe as g&g. adjacent to the restaurant is their bakery and coffee bar, where we grabbed homemade bagels and stumptown coffee the morning prior (and a delicious loaf of pumpkin-parmesan bread)!
lone wolf | 806 w randolph street
great place to grab a drink before or after dinner at girl & the goat or one of the other nearby restaurants (this area is called restaurant row, so there are plenty). it was pretty crowded here, even at 6pm on a friday night, but we managed to snag two bar seats and a couple of good cocktails. they also have a great selection of craft beer and randomly, pie! warning: very loud!
NEAR NORTH SIDE / RIVER NORTH
oak + char | 217 w huron street
kevin read about this new-ish restaurant online, and decided we’d go here for dinner on his actual birthday. great craft cocktails and with regard to food, a very similar concept to girl & the goat with shareable small plates. we ordered a few different menu items, and tried beef tartare for the first time and loved it! the charred burrata was wonderful as well. don’t forget the cider donuts with maple foie syrup – to die for.
shake shack | 66 e ohio street
this is the first chicago location for shake shack, which just opened about a month ago and already seems to have amassed quite a following. this was our first time eating at a shake shack, and we left very impressed: probably my favorite fast food burger ever, great fries, and delicious house-made lemonade (we didn’t get around to trying any shakes). conveniently located near magnificent mile and definitely worth a stop if you haven’t been here before (or if you’re from the east coast and need your fix).
eataly | 43 e ohio street
a mecca of all things italian. on the first level, a market with lots of italian products and local dairy, as well as a few casual eateries, like a panini shop, a gelato stand, and a whole cafe dedicated to nutella. on the second level, there are several more restaurants, each focused on a particular cuisine, like pizza, pasta, seafood, meat + cheese, vegetables, etc., plus a wine and beer shop. the second-level restaurants were quite crowded both times we went, but it’s a fun place to wander around it, and we can vouch for the gelato and the paninis – both were wonderful.
celeste | 111 w hubbard street
an upscale cocktail bar that’s perfect for a special occasion or when you’re feeling a little fancy. men in suits greet you at the door, and direct you to one of three levels – the main level with cocktails and a limited food menu, an upper level (the deco room) with a full-service restaurant, or the garden level, a rooftop bar which unsurprisingly was not open in december. while still busy, celeste was a little mellower than some of the other bars we visited during our trip. inventive craft cocktails with an astronomy theme.
sable | 505 n state street
we didn’t have a wonderful experience here, but i feel compelled to include it because it came highly recommended to us by our waitress at oak+char, and based on reviews, seems to be pretty popular. it’s located inside of a hotel, but feels like a space of its own, and while we had a little snafu in terms of service, the cocktails were great and i’d definitely give it a second chance on a future trip.
OTHER NEIGHBORHOODS, MISC.
goose island clybourn | 1800 n clybourn avenue
goose island is one of the larger breweries in chicago, and one that we’ve always wanted to tour, so tour we did. at this location, they actually only make beer for the attached restaurant and don’t do any distribution, so it’s fairly small. we got a quick tour of the brewery, and then headed into the restaurant area where we were guided through a tasting of several of their more rare beers, which was neat! overall, not our favorite brewery tour ever, but still worth checking out, and they have a great merchandise selection. for $10, you get the tour, the tasting, and a souvenir pint glass to keep, so not a bad deal.
koval distillery | 5121 n ravenswood avenue
it’s not as often that you get to tour a distillery, so we knew we wanted to hit up koval on this trip. i highly recommend this tour – for $10, you get a tour of their facility complete with lots of neat alcohol history and the chance to taste many of their spirits and liqueurs. it’s a little bit off the beaten bath, but worth making the trip for and checking out all the unique things koval is doing. if you want to take anything home with you after the tour, you get 10% off anything in their shop (including alcohol), plus they’ll let you taste anything that you didn’t get a chance to on the tour.
rickshaw republic | 2312 n lincoln avenue
colorful little spot on the north end of lincoln park serving indonesian street food. we opted for the rice table option, which is a 10+ course meal of small(ish) plates for $36/person. not really being familiar with indonesian food, this was a great way to experience a bunch of the different dishes and flavors of the cuisine. they do a great job of including a variety of textures, levels of spiciness, and flavors; we enjoyed nearly every dish. a little pricey, but worth it for a unique experience and supporting this sweet family-run operation. bonus: it’s byob here, and no corkage fee!
second city | 1616 n wells street
comedy club where many famous comedians got their start, including tina fey, stephen colbert, chris farley, and the list goes on. they have multiple shows a night across multiple stages – we saw the main show, but i’m sure you can’t really go wrong here. i’ve been to other comedy clubs before, and they’re all notorious for packing you in pretty tight, but second city took it to a whole new level – just a warning, be prepared to make friends! fairly affordable and there’s not a bad seat in the house!
we hope you’ll find this list helpful if you ever find yourself in chicago! and if you have favorite places that we missed, please leave them in the comments, and we’ll try them on our next trip!