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Weekend Guide to Chicago — explore the windy city!

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Chicago is one of my favorite cities to visit and I can’t wait to call it home soon. The place is overwhelming with food, activities, anything you could imagine! I wanted to compile a list to help someone who has never been or all my favorites thus f...
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Eats

 
Samantha Taylor profile picture
This place is delicious! It’s not complicated sushi, but it tastes so good! Their hand rolls are amazing during Happy hour! Service is incredible, this is my go to rec for sushi downtown!
River North - Sushi San
 
Samantha Taylor profile picture
Book a reservation so you can sit along the river! I felt like I was in Greece at this place. The truffle fries are a must, you get so much and easy to share! The charred pepperoni pizza was delicious too!
Pizzeria Portofino
 
Samantha Taylor profile picture
Great apps and great ramen! We absolutely devoured the food here
RAMEN-SAN
 
Samantha Taylor profile picture
Brunch here was so good. We got steak and eggs and a breakfast pizza that I haven’t stopped thinking about ever since I got it.
Siena Tavern | Modern Italian Restaurant in River North, Chicago, IL
 
Samantha Taylor profile picture
Amazing service! I requested to eat by the river to enjoy the pretty views. Their sliders and truffle fries were tasty!
Porter Kitchen & Deck - Chicago River American Restaurant
 
Samantha Taylor profile picture
I’m not the biggest fan of deep dish pizza, but I think it’s right of passage to try it once in Chicago, so why not at a historic place?
Uno Pizzeria & Grill
 
Samantha Taylor profile picture
Get deep dish here too while you’re strolling Michigan ave!
Italian Restaurant In Chicago | Labriola Ristorante Chicago
 
Samantha Taylor profile picture
Their menu is so yummy! And the ambience was so cool, felt so private!
The Izakaya | Japanese Bar & Lounge | West Loop, Chicago
 
Samantha Taylor profile picture
an upscale restaurant that still feels casual! Can enjoy a tasty dinner while watching the game!
Bar Siena | Casual Italian Restaurant in Chicago
 
Samantha Taylor profile picture
the vibes and energy here are strong. Have a fun lunch here and explore wicker park!
Paradise Park
 
Samantha Taylor profile picture
so many locations and a staple of Chicago. The Italian beef truly is delicious!
Restaurant Locator | Portillo's
 
Samantha Taylor profile picture
my personal favorite option for deep dish. Delicious flavors (I recommend hot honey) that isn’t too cheesy, and don’t sit heavy in your stomach!
Lou Malnati's, the Best Chicago Deep Dish Pizza Restaurant

Activities

 
Samantha Taylor profile picture
This is a must! Learn about the city and its history with gorgeous views while coasting on the river! Worth every penny
2025 Chicago Architecture River Cruise - with Trusted Reviews
 
Samantha Taylor profile picture
Get a Lyft bike or electric scooter, or even walk this path! You get skyline and lake views that are unbelievable! A nice break from the busy parts of the city!
Lakefront Trail
 
Samantha Taylor profile picture
This is one of the largest indoor aquariums. A great activity for kids and adults. The dolphin show is so fun too!
Shedd Aquarium
 
Samantha Taylor profile picture
This place is gorgeous and free! A must go along with the zoo
Conservatory Reservations | Lincoln Park Conservancy
 
Samantha Taylor profile picture
This zoo is FREE and so amazing! You must go to this. Such a fun activity for the day
Wildlife Experience in the Heart of Chicago | Lincoln Park Zoo
 
Samantha Taylor profile picture
Come to a famous spot to experience the comedy of Chicago! I went on an open mic night and got to see the aspiring comedians. It’s such a special memory for me. I had so much fun here!
Chicago’s Best Stand Up Comedy Club | Laugh Factory
 
Samantha Taylor profile picture
Go to one of the most famous buildings in Chicago! See the whole city at a height you’ve never been before!
Skydeck Chicago | Home
 
Samantha Taylor profile picture
One of the many vintage shops in wicker park! Stroll down the street and pick up some sick finds! Some even have a photo booth where you can get your pics printed!
Home | Layers Chicago
 
Samantha Taylor profile picture
such an impressive zoo and it’s free!!
Wildlife Experience in the Heart of Chicago | Lincoln Park Zoo

Coffee Shops and Sweet Treats

 
Samantha Taylor profile picture
Such good coffee, pastries, and eats! Their muffins are huge and easy to share. Bananas foster latte and the bacon and egg croissant sandwich are my favs!
Goddess And The Baker | Cafe in Chicago & WI
 
Samantha Taylor profile picture
The donuts and coffee were so good! It made for a great Sunday morning treat and start to the day!
Stan's Donuts | Coffee, Donut Shop in Illinois
 
Samantha Taylor profile picture
This place is stunning. You can either stay at the front for a coffee, or go to the back to enjoy a meal!
Venteux Café – French Café in Chicago
 
Samantha Taylor profile picture
Delicious treats and coffee! I loved my sandwich from here, this is one of my fav places!
Oud Coffee & Cafe
 
Samantha Taylor profile picture
Get your coffee break while walking Michigan ave! Such a cute spot! And the merch is adorable!
Ralph’s Coffee
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Samantha Taylor profile picture
This place has so many locations thank god! The flavors are so tasty, an expensive scoop but I haven’t stopped thinking about it since!
Jeni's Ice Creams
 
Samantha Taylor profile picture
These cookies are massive. In my opinion, much better than crumbl cookie.
Levain Bakery
 
Samantha Taylor profile picture
Delicious gelato with plenty of seating to enjoy it with your friends!
Amorino Chicago - Westloop
 
Samantha Taylor profile picture
I’m obsessed with Swedish candy, and so cool to find it locally here for reasonable prices!
lil sweet treat | globally sourced sweets