12. Raise a Glass at Old Town Ale House
What is it?
A legendary 5am dive bar with attitude, character and unforgettable artwork.
Why go?
This Old Town institution draws everyone from neighborhood regulars to visiting performers from nearby theaters. Cultural icons like Anthony Bourdain and film critic Roger Ebert counted it among their favorites.
Don’t miss:
The famously cheeky paintings of politicians by house artist Bruce Elliott—conversation starters guaranteed.
13. Cheer at the United Center
What is it?
Chicago’s home for pro basketball, hockey and major concerts.
Why go?
Catch the Chicago Bulls or Chicago Blackhawks in action, or see global superstars take the stage. The arena’s energy is electric year-round.
Don’t miss:
Snap a photo with the iconic Michael Jordan statue—and sample elevated stadium eats from local restaurant partners.
14. Sip World-Class Saisons at Is/Was Brewing
What is it?
A bright Ravenswood brewery specializing in saison-style beers.
Why go?
Located along the city’s famed “Malt Row,” Is/Was Brewing has earned international recognition for its nuanced, farmhouse-inspired brews.
Don’t miss:
Trivia Tuesdays and Bingo Thursdays—perfect excuses to linger over another pour.
15. Play All Day at Elston Electric
What is it?
A retro arcade and pinball paradise inside the Salt Shed’s former boiler room.
Why go?
With more than 100 games, Elston Electric caters to everyone—from serious pinball wizards to casual gamers. By day it’s family-friendly; by night, it transforms into an adults-only playground.
Don’t miss:
Pinball League Nights, where competitors battle for prizes and bragging rights.
16. Plan a Romantic Escape
What is it?
Chicago’s most swoon-worthy experiences.
Why go?
Whether you’re booking a luxury spa treatment, reserving a table at a candlelit restaurant or planning a creative date night, the city offers endless ways to spark romance.
Don’t miss:
Seasonal pop-ups, rooftop dinners and cozy winter cocktail bars that set the perfect mood.
17. Indulge in a Spa Day
What is it?
Chicago’s top spas for rest and rejuvenation.
Why go?
After a busy summer—or a frigid winter—there’s no better reset than a massage, facial or thermal bath session. The city offers options for every budget, from ultra-luxury retreats to neighborhood wellness spots.
Don’t miss:
Pair your spa day in Bucktown with a burger at Small Cheval just across the street.
