Ultimate Chicago Bucket List

SUMMERTIME CHI BABY, if there’s one place you have to experience in your life, it’s Chicago in the Summer. I recently headed out on my nomadic adventures a month ago to city hop in places I’ve always wanted to live but avoid the dreaded Winter weather and first up: Chicago. 

Living a month at The Oakwood Residence apartments was a DREAM. Right in the heart of the city with floor to ceiling windows and did I mention… MY SISTER. Our month was jam packed with activities, eating out, exploring, drinking and partying and now I present you the ultimate Chicago Bucket List (with my honest opinions, of course). 

Food: A Girl’s Gotta Eat

Aba: Infamous Mediterranean restaurant located in the Fulton Market District. You have to make reservations a month in advance to get a spot. I thought the veggie options were good but not amazing – must try the Spicy Hummus. I didn’t get a chance to try the drinks either, but definitely one to add to your list to say you went. 

Bombay Wraps: FIRE. Best Paneer Tikka & Samosa Chaat wraps EVER. I had it multiple times for lunch.

Goddess & The Baker: My fave everyday brunch spot – amazing coffee and lattes, love the sandwiches and wraps. A must for those on the health grind.

Eately Osteria: My favorite Italian restaurant hands down. Located in the heart of Eataly, this place had peach bruschetta and ravioli that was to-die for. They also have a burrata bar (say cheese!)

Beatnik on The River: VIBES. Reserve this spot during the night for drinks and just gaze at the river while enjoying some drinks. It’s beautiful. I haven’t had the food, but options seemed limited for vegetarians.

Sunda: Another Chicago staple, deliciously good Asian-Fusion food. I loved the vegetarian sushi here, they also had a lot of tofu options.

Ramen-San: The place for all things Ramen – so many amazing options, I loved the veggie broth here along with customizing my ramen with add-ons, don’t forget to add a lot of chili. 

Pizza Portofino: Located right on the river, the food was very average but the ambiance was beautiful. I would maybe stop by here for a mid-day drink.

Cabra: A Peruvian-inspired rooftop that has a lot of small plates in tapas format. The vegetarian options were limited but definitely interesting to try. We unfortunately visited when it was raining but highly recommend checking it out when it’s sunny because the pool area of the rooftop is open then. 

Corey’s NYC Bagels: Bagels were very average in Chicago but this place is one of the best ones! Must try the Onion & Chives cream cheese.

Jenni’s: The best ice-cream spot in the city! The line is always out the door but the dessert is so worth it. I want to literally try all the flavors – my favorite is the Gooey Butter Cake.

Pink Taco: Another quick bites kinda eat especially on a Taco Tuesday. They had a delicious Sweet Potato taco, definitely worth visiting for Happy Hour. 

India House: My sister brought this home one day and I had a few bites – one of the better Indian food places. I judge a place by the Paneer Tikka and this one passed.

Deep Purpl: This one’s for the açaí lovers! The only place I could find remotely as good at the SF açaí spots.

Experiences: A Girl’s Gotta Live

Neon Summer: Cute pop-shop with Instagrammable spots and activities like axe throwing, go-karting and mini-golfing. 

Kayaking the River: Rent a Kayak for a couple of hours and take it out on the river for a fun day-time activity.

Navy Pier: Walk around Navy Pier and grab some ice-cream and enjoy the vibes. 

Biking Lake Shore: Rent out one of the electric Divy bikes and bike around the city during the day and hit Lake Shore for sunset.

Starbucks Reserve: The largest Starbucks in the world – for all my coffee and cocktail lovers. The espresso martini here is the best I’ve ever had.

Aviary: If you’re able to get reservations, DO THIS. A whole ass cocktail experience. 

Aire Ancient Baths: If you’re in the mood for a massage and healing experience, you must check out the heated pools at Aire. One of the best spas I’ve experienced, check out my TikTok for more information.

Drinks: A Girl’s Gotta Party

Fremont: All-you-can-eat and all-you-can-drink brunch with day club vibes. It doesn’t get better than this. Make sure to book seating on the rooftop.

London House: My favorite rooftop in Chicago, a MUST during sunset. 

Utopian Tailgate: It’s a playground for adults. Water guns with tequila. Beer Pong. Connect 4 with shots and so much more. 

Federales: Infamously knowing for taking your shot and throwing ice on a bell. Always a Friday happy hour vibe.

Bounce: The most popping’ club in River North – the music is so lit. 

Electric Night Club: I personally wasn’t the biggest fan but if you’re into hardcore EDM, check this place out.

Hampton Social: An aesthetically pleasing bar with giant fishbowls for alcohol. 

El Hefe: My absolute favorite bar to go to on the weekends – ONLY HIP HOP MUSIC. 

Offshore: Cute vibey bar at the end of Navy Pier, try getting a spot outside.

Recess: Cute outdoor bar with lots of seating for big groups. 

Bar Avec: Popular rooftop in River North with handcrafted cocktails that are delicious!

Tunnel: A club located above Treehouse that’s fun to go to on the weekends – music can be a hit or miss.

Shore Club: A beach party!

Howl at the Moon: Live music and $1.50 drinks on event days!

Prysm: EDM club, a little far from everything but still worth checking out. 

Hubbard Inn: Restaurant turned nightclub in River North, loved the wall decor here.

Joy District: A bar downstairs and a club upstairs – another must check out.

Treehouse: LOVED this place, way less crowded than Tunnel and amazing music. 

Pizza: A Girl’s Gotta… It’s Freakin’ Pizza

Pequod’s: MY WINNER FOR BEST DEEP DISH. And yes, pineapples are a must.

Lou Malnati’s: Overrated IMO, wasn’t the biggest fan of the sauce. 

Giordano’s: I didn’t get to try this one but it’s supposed to give the others a run for their money.

Pizza Parlor: LOVE for non-deep dish pizza, they have super unique pizzas that I’ve never had before.