Things To Do
Chicago Architecture Center River Cruise
We've been on this tour now 5 times, and this is our go-to activity for anyone visiting us here. Hosted by the Chicago Architecture Center, you'll learn all about the iconic skyscrapers in the city -- plus there's a full bar!
North Avenue Beach
Most people don't realize that Chicago is also a beach town! This is one of our favorite beaches in the city and the most popular for its skyline backdrop. There's a snack bar and cocktail bar on site and connection to the Lakefront Trail and walking bridge into Lincoln Park.
Lakefront Trail
18-mile path along Lake Michigan that's great for walks along the water, or rent a bike at one of the many Divvy stations along the trail! You'll pass several beaches and have killer skyline views the whole way.
The Up Room
One of the best rooftop bars in the city that also happens to be in our neighborhood! Enjoy a panoramic view of the skyline with some A+ cocktails. Yes, the view is priced in but well worth it!
Small Bar
A legitimate contender for the best burger in Chicago. This is an excellent neighborhood bar with two flat top grills serving burgers, fries, and cheese curds. Order "the pleaser" and grab a spot on the patio - you're in for a treat.
Big Star Tacos (Wicker Park)
A Wicker Park staple with great authentic tacos on house-made tortillas and strong margaritas. They have large indoor and outdoor seating areas including a bar with a surprisingly impressive bourbon selection.
Estereo
Logan Square open-air cocktail bar with a Latin American menu, vintage vinyl spinning on the turntable, and great cocktails for mezcal, pisco, and rum lovers. On weekend evenings expect a DJ playing Latin American records!
The Art Institute of Chicago
Nature Boardwalk at Lincoln Park Zoo
CloudBar at 360 CHICAGO
Go to the top of the Hancock Building for a great view of the lake and entire city! Plus there's a full bar and a "sip + tilt" option if you're not too afraid of heights.
Wrigleyville
Home of the Chicago Cubs and several large, sports-themed rooftop bars and restaurants. Our favorites are Old Crow for live music and a country atmosphere and Sluggers for the batting cages on the top level.
Bub City
Wish you could teleport to Nashville for a meal? We've got you. Check out this River North staple for beers, bourbon, BBQ, and live country music. Hard to go wrong when brisket is involved.
KAI ZAN (Sushi + Omakase)
An intimate sushi and sashimi restaurant in West Town featured in several Chicago food guides. They offer the most affordable omakase menu in the city that doesn't hold back whatsoever and is worth going out of your way for.