The Cool Girl Travel Guide: What To Do in Chicago

The Windy City: Best known for deep dish pizzas and Wrigleyville.

I tackled Chicago in 48 hours and made sure I got the scoop on where to eat and what to do.

I enjoyed this cute little city and have to give a personal shout out to my best friend/assistant, Cilia, for organizing my psycho list and putting together our itinerary. I mean seriously, round of applause.

So, here it is guys. My mega post of all of the GO-TO spots in Chi-Town.




I stayed at this industrial-style loft which is located about 25 minutes outside of the city. I rented a car so it was definitely worth it! It was super vibey and was very practical for what we needed, loved it!

Chicago Airbnb



Beatnik on the River

Like helllooo alfresco urban outfitters! We got extremely lucky with the weather so we were able to sit outdoors and enjoy a fresh pitcher of sangria by the water. The menu is Mediterranean cuisine so if you dig it I recommend the beet hummus and wild mushrooms as an app.

soho house couchSoho house


The Allis at Soho House

Such a chill spot, even Kanye knows it (for real, he was actually right above where I was sitting in that picture)

You can drop in for coffee, fresh juices or little bites. Perfect little WeWork nook.

113-125 North Green

Paradise Pizza

Paradise Pizza

Festive new pizzeria and bar located in Wicker Park. I obviously lived inside this bohemian hut the whole time. Order their pomegranate margaritas!!!

1913 W North Ave


Restoration Hardware’s 3 Arts Club Cafe

Industrial-chic cafe nestled right in the middle of a furniture store. I ordered a couple of spritz and a cheese board. Really cute place for a date or a casual hang out.

1300 N Dearborn St

Bar Siena

Contemporary Italian fare served in a stylish rustic space with a buzzy bar and patio. Order the duck Mac and cheese, gnocchi, or the burger.


Stan’s Donuts

These donuts were PERFECT- no wonder everyone raves about them. I’m literally drooling writing this post.


RM Champagne Salon

Champagne, raw bar, artisanal cheese and chandeliers. The pillars of perfection.

116 N Green St

pizzadeep dish

Deep Dish Pizza

I was told the best deep dish pizza in Chicago was Giordanos, but I’m sorry to say I wasn’t impressed- especially since I’m from NY. My friend who is a Chicago local recommended Pequods which definitely seemed more up my alley. I’ll have to check that out next time.


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Joe and the Juice

Not gonna lie, came here for the pink cups.

8 East Huron St.


Limitless Coffee and Tea

Charcoal infused glitter lattes are the MUST-order item on the menu! Not only were they super pretty, but were delicious also.

675 N Wells St

owl larkowl lark 2

Owl and Lark

Eeeeeks, this place is so cute. I just love homey little botanical cafes. This one is a bit of a hike outside of the main city, but worth it for the pretty ambiance.

41 South La Grange Road, La Grange


Real Good Juice Co.


1647 N Wells St



Tucked away in one of the smallest and oldest alleys in the Loop. Asado is interior and exterior goals.

1432 W Irving Park Rd


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The Skydeck

A Chicago quintessential, I’m happy I can finally cross this off of my bucket list. The Skydeck is on the 103rd floor of the Willis Tower and is an interactive, cultural exhibit.

233 S Wacker Dr


Walking Around

Love seeing old world charm in historical districts.



The magnificent mile encompasses more than 460 retailers, so you can literally shop til you drop.



I came here for the gram, but if you want REALLY good donuts scroll up to the food section of this post.

Blue door kitchen

Blue Door Kitchen and Garden

I unfortunately didn’t get an opportunity to eat here, just came for the pretty blue door.

52 W Elm St


The Art Institute of Chicago

One of the largest and oldest art museums in the United States! TIP: Buy bundle tickets for the art museum + Skydeck to save some money.

111 S Michigan Ave

I hope my big ass travel guide helped you guys if you ever plan on booking a trip to Chicago!

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