Although I’ve been to Chicago several times as a kid, this was my first time exploring the windy city. Let me just say… they weren’t exaggerating when they nicknamed Chicago “The Windy City.” See below for all of my fave places to get food, drinks along with other fun things to do!
FOOD & DRINKS
Giordano’s – You can’t go to Chicago without having deep dish pizza. This was my first time and I was full after one slice… It’s worth trying, but I still love my regular pizza haha. Another suggestion we got from several people was Lou Malnati’s.
City Winery Chicago – By far one of my favorite experiences here! You and some friends are able to have lunch or dinner in a dome on the side of the Chicago River. For approximately $85/guest ($60 food and beverage minimum per guest), you get to enjoy drinks, food, and games with friends! All guests must be 21+.
Little Goat Diner – LOVED this brunch spot! It was aesthetic and delicious. I got the okonomiyaki which is Osaka street food with pork belly; soooo good. I would highly recommend.
Girl and the Goat – Probably one of my favorite restaurants during our trip. The executive chef competed on Bravo’s Top Chef, winning the competition. She is also the owner of Little Goat Diner. Food is served on shareable plates for the table. Some of my faves were the sauteed green beans, shishito peppers and the pan-roasted halibut. Definitely try to make reservations!
Crisp – Holy moly, the best wings ever. First of all, the wings are HUGE. Secondly, all of the flavors were delicious. My favorite was the Seoul Sassy flavor. If you aren’t a wings person, they have a ton of other options. I highly recommend trying this place out!
3 Arts Cafe – Loved the atmosphere of this place! Although it’s located in a fancy furniture store, this cafe is a nice place to have a drink, a bite to eat and relax. And definitely Instagram friendly 🙂
Sawada – Such a cool coffee shop. I mean, what other coffee shops have a ping pong table, pinball machine, and a Supreme punching bag?! There’s also a bar and restaurant, so expect plenty of seating.
The Hampton Social – Another Instagrammable place! If you’ve seen the photo of me with a “rose all day” sign, this is where it’s from! We only got drinks from here (along with free truffle fries when you check into Yelp).
Cindy’s Rooftop Bar – One of the prettiest views in Chicago. From the bar, you can see Lake Michigan, The Bean and part of downtown. We didn’t get to truly enjoy the outdoors because it was so cold and windy, but I’d definitely recommend checking it out!
Bar Siena – Get the #8. Enough said.
Portillos – Almost every lyft driver recommended this hot dog place to us. I think it was too hyped up for me… wasn’t one of my favorites.
Garrett Popcorn – The Chicago mix popcorn is a popular snack here. A combination of cheddar and caramel flavors, yum.
THINGS TO DO
Second City Comedy Club – If you’re going to Chicago, you HAVE to attend a show here. This was HANDS DOWN the best comedy show I’ve ever been to. We went to Algorithm Nation or the Static Quo show. Second City Comedy Club is where many stars got their starts such as Tina Fey and Steve Carrell.
Chicago Cubs Game – For all your sports fans, you can’t go to Chicago without visiting Wrigley Field! Beautiful stadium!
Flight Club Darts – Had so much more fun that I thought I would here! This is a bar/restaurant, but also has dart games everywhere! I’ve never reaaally played darts before, so it was a learning experience, but it was fun!
Shedd Aquarium – One of the biggest aquariums I’ve been to! It was definitely worth going to. They even have rescue seals and dolphins!
Museum of Contemporary Art Chicago – This is a nice museum to go to if you want a relaxing activity. Beautiful art.
Millennium Park (The Bean) – You can’t go to Chicago without visiting The Bean and taking awesome
Magnificent Mile – There are several stores to shop at on Magnificent Mile! From Burberry to Zara to Uniqlo, there’s probably a store for everyone. And all the stores are huge!
Eataly – This place was awesome. You can have wine, gelato, pasta… basically anything Italian. This was definitely a good stop.
Some places we didn’t have time to visit were Navy Pier and the sky deck. I’d definitely check these out if you have the time! Perfect for pictures too 🙂
Hope this guide helps! Let me know if you guys have any questions in the comments below! 🙂