24. Dance the Night Away at Smartbar
What is it?
A legendary club in the city that gave birth to house music.
Why go?
Experience authentic Chicago house in an underground setting where DJs, dancers and drag performers keep the energy pulsing late into the night.
Don’t miss:
The iconic weekly Queen! dance party.
25. Discover Robie House by Frank Lloyd Wright
What is it?
A Prairie School masterpiece often called the cornerstone of modern architecture.
Why go?
Located in Hyde Park, Robie House showcases Wright’s signature horizontal lines, art-glass windows and harmonious integration with its surroundings.
Don’t miss:
The intricately designed furniture and stained-glass details—also created by Wright himself.
26. Explore Avondale—One of the Coolest Neighborhoods on the Planet
What is it?
A Northwest Side neighborhood just beyond Logan Square that’s packed with personality.
Why go?
Recently named one of the world’s coolest neighborhoods, Avondale blends historic two-flats and bungalows with colorful street art, repurposed warehouses and lively Polish and Latin American businesses.
Don’t miss:
Follow a local-crafted neighborhood itinerary—cafés, dive bars and hidden gems abound.
27. Soak & Cruise with Chicago Boat Company
What is it?
Motorized boats fitted with steaming hot tubs.
Why go?
Who says boating season ends in winter? Float down the Chicago River in heated water with friends (BYO drinks welcome). Cruises last 90 minutes and fit up to six people.
Don’t miss:
Dock in Avondale and grab a nightcap at nearby Judson & Moore Distillery.
28. Grab a Chicago-Style Dog at Superdawg Drive-In
What is it?
A retro 1940s drive-in famous for its Chicago-style hot dogs.
Why go?
Carhops still deliver to your vehicle. Their signature dog comes topped with mustard, onions, piccalilli and a pickled green tomato—served in a cute box with fries.
Don’t miss:
Swap the fries for Superonionchips—crisp, golden and addictive.
29. Hear Live Jazz at Green Mill Cocktail Lounge
What is it?
An Uptown jazz institution with Prohibition-era roots.
Why go?
Once frequented by Al Capone, the Green Mill now hosts nightly jazz ranging from bebop to experimental sessions. It’s moody, historic and authentically Chicago.
Don’t miss:
A photo beneath the glittering marquee before stepping inside.
30. Gallery Hop Along Chicago Avenue
What is it?
A thriving cluster of contemporary art galleries in West Town.
Why go?
Stretching between Ashland and Wood, this strip offers a free, walkable art tour featuring spaces like Matthew Rachman Gallery and other leading contemporary galleries.
Don’t miss:
Design lovers can browse vintage furniture by icons like Vladimir Kagan and Eero Saarinen.
