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My Favorite Spots to Eat in Chicago


Shoes: c/o indigo rd (also love these and these!) // Sweater: Nordstrom –also comes in several other colors!) very similar sweater in mustard color here, here, and here // Jeans: old (similar here, here, and an under $100 version here

Over the past week, we’ve talked where to shop in Chicago, what to do in Chicago, and now the grand finale in my three part series: where to EAT in Chicago! (Oh, and what to wear to all of my favorite restaurants, too.)

It’s no secret that eating is one of my favorite pastimes. Neal admits that he never really had an interest in food before he started dating me. (Is that embarrassing or should I take this as a compliment?) Going out to eat is one of our very favorite things to do together, and you could say we’ve tried a lot of places over the past few years. So today, I’m teaming up with indigo rd shoes again to bring you my list of go-to windy city spots to grab a bite to eat. (Or something sweet!)

Stan’s Donuts

Okay, okay. Now, if you know me, I’m not typically a big “sweets” person, so the fact that I’m starting off this list with a donut shop should come as a pretty big shock to you. However, Stan’s is just THAT good. Don’t fool around with the basic glazed donuts here, you have to get the Biscoff Pocket donut. You know those delicious little Biscoff cookies they serve on airplanes? It’s kind of that flavor, but donutified and literally the best thing you’ve ever tasted. They also have great coffee, and the cutest decor. I always look forward to coming here! (When we shot this, the weather had just started to feel like fall outside, and it was the perfect day to cozy up in these indigo rd suede booties and a turtleneck to take a donut break!)

Big Star Tacos

No exaggeration, Neal and I probably go to Big Star about once a week for tacos. We’re even getting Big Star catered for our engagement party–that’s how good it is. Plus, they have a huge outdoor patio–tough to beat in the summer! You must go with the steak tacos–it comes with this crazy gourmet cheesy sauce that’s the best thing you’ve ever tasted. And their margaritas–I don’t even LIKE margaritas, but here, they’re fresh and phenomenal.

Au Cheval

An Au Cheval burger is a burger that is well worth the wait. This upscale diner has made itself known for having the best burger in town. (Get it with an egg on top!) The decor is fun, and there are plenty of cool cocktail bars to wait at after you put your name in! (Plus, they’re open late!)

Small Cheval

As you can probably guess, Small Cheval is Au Cheval’s little cousin, located in my ‘hood of Wicker Park. Their burgers aren’t really the same, so you can’t compare them, but ridiculously tasty. They only serve burgers, fries, and great beer here, and the restaurant is tiny with communal seating. It’s a really fun place for a cheap date night.

Antique Taco

Another favorite taco place–you really can’t compare Big Star to Antique Taco. It’s like apples and oranges. Antique Taco is a charming little restaurant where you order at the counter. It has antique decor and just a handful of tables, and the best Chicken tacos you’ve ever had. (They’re sweet, spicy, and so good!) Their enchiladas are also to die for–make sure you get an Agua Fresca too!

Los Comales

If you’re looking for REAL (i.e. not trendy) Mexican food, you’ve gotta go to Pilsen. (One of my favorite neighborhoods in the city.) Los Comales is where it’s at when it comes to authentic tacos. The steak tacos are so, so good. Oh, and they’re like $1.50. Cheap cheap cheap. Just go, please. Go.

Cindy’s Rooftop

My go-to recommendation for any out of town visitors staying downtown. Cindy’s is at the tip-top of the Chicago Athletic Association hotel, and has one of the best views of the city–the only view, to my knowledge, which gives you an amazing view of the harbor and the lake along with the skyline. Their cocktails are awesome, and their brunch entrees are huge and made for sharing! It’s one of the most beautiful restaurants in Chicago and always a fun time. You can see my full write-up on Cindy’s (and photos!) here.


Neal and I went on our first “real” dinner date at Frontier! If you want something totally new and different, this is the place for you. Their specialty is “game”–so you’ll find things like venison and wild boar on the menu. (Don’t worry, they have plenty of “normal” stuff too!) Their lollipop chicken wings are amazing, and my favorite part is that they have a covered patio year-round. (With fireplaces in the winter!)

La Scarola

When you think of “old school Italian” you think of La Scarola. Lot’s of tiny tables smushed together in a bustling, busy restaurant–and some of the best Italian food in the city.

Bar Ñ

Neal and I just stumbled upon Bar Ñ recently, and is equally as delicious as it is fun. It’s an Argentinian “lounge”–they have a live DJ, make amazing cocktails (the mojitos are to die for) and served up the best steak we’ve had in a long time. We each had two drinks and a steak and the total bill was about $50.


Girl & The Goat

Everyone always asks me: Does it live up to the hype? YES. Absolutely. Go, go, go. Some of the best meals I’ve had in Chicago have been here! I’ve been 4 times, and each time it’s been equally wonderful. (If you don’t know, Girl & The Goat is Top Chef, Stephanie Izzard’s restaurant). You’ll have to make a reso far in advance, but if you didn’t happen to plan that far ahead, you can usually walk in and grab a seat to eat at the bar! (I mean, it’s worth a try–what do you have to lose?) Make sure to let your waiter weigh in on your choices–they’ll never steer you wrong!


A fun place to go if you’re staying near the downtown area. Quartino is trendy, fun, with great food and decent prices and always hopping with twenty-somethings. I’ve frequented this place probably more than any restaurant in Chicago over the years, both with friends and out of town guests–it never disappoints! (Warning though: It gets very loud–so go somewhere else with your parents ;-P)

Summerhouse Santa Monica

Summerhouse is one of my favorite restaurants in Lincoln Park–it doesn’t matter when you visit this place, it always feels like a sunny summer day inside. Their food is classic American bistro fare, always delicious. (Especially the burgers, salads and tacos!) Make sure to get a skillet cookie for desert!


Bavette’s is hands down, the best steakhouse in the city. You can also BYOB–their policy is that you just have to pour one glass of wine to give to a neighboring table! How fun is that? The vibe, unlike most stuffy steakhouses, is a nearly pitch dark speakeasy with cozy leather booths and fantastic service. We went here for Valentine’s Day once and it’s still one of my favorite dates we’ve ever been on.

Le Colonial

Speaking of favorite dates we’ve ever been on, we decided to pop into Le Colonial for an impromptu date-night dinner the first Christmas we were dating. We had been shopping on Michigan Avenue all day and were making our way through the Gold Coast shops and, despite being severely under dressed, decided to go in. Their specialty is vietnamese-french fusion, and it’s some of the most unique, delicious food you’ll ever have! The ambience is insanely romantic, and perfect for a date.

Ada Street

Ada Street is an adorable little restaurant that sits in essentially a back alley amongst a bunch of warehouse buildings. If you think your Uber driver is taking you somewhere remote to murder you, you’re in the right place. They have a big garage door that they open in the summer, and have a fresh farm to table menu.

Gemini Bistro

A little gem of a bistro that is pretty much only known to locals in Lincoln Park. They make the best sidecars I’ve ever had. Menu items not to miss: steak frites, short rib, short rib ravioli, and their Gemini Bistro salad.

The best thing about Chicago (as you saw me mention here) is that you can really get away with wearing jeans just about anywhere. This outfit is pretty much the same variation you’ll see me wearing throughout winter and fall, and one that is universally acceptable at any and all of the above!

I love these boots in particular because the heel is the perfect height–it’s low enough that you can walk around in them all day (grabbing a donut at Stan’s or tacos at Los Comales) and be totally comfortable, but tall enough that they dress up your basic jeans and make them suitable for a place even as high-end as Bavettes! (We’re Midwesterners after all, nobody really cares what you’re wearing!)

Of course, there are times where you want to dress up–and if so, I’d recommend something along these lines if you care to get a little fancier, but it’s really not necessary!


What are your favorite spots in Chicago? What other local reccos would you like to hear about? 

This post brought to you in partnership with indigo rd. Thank you for supporting the brands that help keep this site up and running! 

Photos by Julie Kennedy