Chicago Travel Guide

A Chicago Travel Guide for the food obsessed!

Happy Wednesday y’all! I’m recapping our Chicago trip from a few weeks ago, and now I’m craving a lemon pistachio donut (and the blueberry fritter) from Stan’s Donuts. Tyler & I are both June babies, only 15 days apart, so we ventured to the windy city for some birthday celebrations. Chicago never disappoints and we had the most amazing weekend. Keep reading to see what we did during our trip!

P.s. We’ve been to Chicago several times over the past year or so, and for whatever reason I’ve never sharing a Chicago travel guide with y’all before. Because it’s over due, I’m including some places to eat & visit that we’ve loved in the past!

Where to grab coffee:

The Goddess & The Baker

I saw their rainbow latte on their Instagram & knew I had to get my hands on one! It was delicious by the way.

Stan’s Donuts

We kicked off our trip to a morning trip to this bakery, and I’m not even being dramatic y’all, they might have been the best donuts I’ve ever had (next to North Lime Donuts, of course)! We got several to try a little bit of each, and we might or might not have finished all 4… My favorites: the lemon pistachio, the blueberry fritter & the biscoff pocket. SO GOOD! Oh, and the coffee was good too 😉

Heritage General Store

We visited this little coffee shop when we were up for the World Series last fall, and it was the cutest little spot.

Dress / Jack Rogers c/o / Sunnies / Gucci Bag

Where to grab Brunch/Lunch:

Left Coast

Tyler & I grabbed their pancakes & avocado toast here last fall & I loved it! Tyler wasn’t sold, but it is definitely a place to grab a healthier(ish) quick bite.

Summer House

I was obsessed with this place y’all! The food & the atmosphere were hard to beat. If you’re into mexican brunch dishes then get the breakfast tostadas.

Hampton Social

Home of the Insta-famous ‘rosé all day’ wall! We had lunch here last summer when I was in Chicago for a bachelorette party, and it was so fun. I don’t remember the food being amazing, but the atmosphere & rosé made up for it.

Three Arts Club Cafe

If you’re not familiar, this cafe is located in Restoration Hardware, and the entire store is #goals. The burrata & burger were delicious!

Where to grab Dinner:

Happy Camper

Y’all, this place is awesome! Located in Old Town, it’s a great place to grab a casual dinner. The restaurant is so cool, and they even have tire swings as seats at the bar. How cool is that?! They have pretty good pizza and even better appetizers.

Joe’s

 Think old school steak house with amazing food. If you’re looking for steak in Chicago, get you a reservation at Joe’s.

Sunda

Our Chicago native friends recommended this Asian restaurant as their favorite restaurant in the city! If you like Asian food, then you need to try this restaurant. It was so, so good! I’m still dreaming of their brussels sprouts salad.

Hub 51

We did dinner here for the bachelorette party and it was the perfect place for a big group. They cater to larger parties and the food was delicious!

Where to grab a drink:

Cindy’s Rooftop

If you’re in Chicago and you want a good view of the “Bean”, grab a drink here! It overlooks Millennium park and has really good cocktails. However, we did hear from several people to skip the food, so I can’t vouch for the food, but I highly recommend their cocktails.

Pops Champagne

We grabbed some bubbly here when we got into town, and it was a classy spot for some champagne. I don’t know if I would go out of my way to grab a drink here again, but it’s a cute spot if you’re close by.

Joy District

This bar has the cutest rooftop area! It was located near Sunda, so we stopped by for a drink on Friday. It gets really crowded though, so plan accordingly.

London House

I had some drinks here with some gals last summer and the view from their rooftop is incredible! I highly recommend if you’re looking for a rooftop to grab some cocktails.

Three Dots & A Dash

A tiki bar in Chicago? Yes, please! The bachelorette party loved this bar.

Bub City

If you’re looking for a fun bar without the “club” vibe, then this bar might be the place for you. It’s a country bar and so fun! It’s our Chicago friends’ favorite bar.

The Pony

Okay, I have to throw this in for my CATS fans! The Pony is the UK bar in Chicago and if you’re in town and looking for a place to watch the game, get on over to the Pony! We’ve been several times to watch a game, and always see someone from Kentucky. The food isn’t bad either.

Top / Shorts / Tassel Earrings / Gold Cuff c/o / Gold Link Bracelet / Bag / Sunnies

What to do in Chicago:

Catch a Cubs Game

Visit Millennium Park

Shop!

Enough said!

Get tickets to The Second City

Y’all, I would go back see a comedy show at The Second City in a heartbeat. We went for the first time during our most recent trip and it was hilarious! We saw the “Best of The Second City” show, we laughed all show long!

Visit the Flamingo Wall

If you’re a sucker for an Instagram photo, then hop on over to 601 N. Wells St. The flamingo wall is a sight to see!