Things To Do
Laugh Factory
This outstanding stand-up spot was the second stop of our first Chicago date
Kingston Mines
This blues club was the third stop of our first Chicago date. See if you can catch Joanna Connor's set.
Kasama
Delectable bakery by day, Michelin star Filipino tasting menu by night.
Chiu Quon Bakery
Chinatown bakery with excellent egg tarts - pair with a bite from nearby Yummy Yummy Noodles. Family friendly.
Improvised Shakespeare Company
The most impressive improv comedy you'll see, featuring Shakespearean language and themes.
Chicago Architecture Boat Tour
Popular with tourists and locals alike to marvel at our city's ever-changing skyline. Family friendly.
Chicago Cultural Center
Take in the largest Tiffany glass dome in the world at Preston Bradley Hall. Family friendly.
Northerly Island
Urban oasis - get outdoors while staying downtown with a walk through this rewilded airport. Family friendly.
Shedd Aquarium
Amazing exhibits from sharks to paddlefish to jellyfish. Family friendly.
Garfield Park Conservatory
If Chicago spring isn't doing it for you, step into wonderfully cultivated tropical and desert climates under glass. Suggest pairing with a meal from nearby Inspiration Kitchens to support a good cause. Family Friendly.
The Second City
Classic spot for sketch comedy. They run several shows, and the Main Stage and etc Stage are reliably hilarious. Family friendly shows available.
Sofar Sounds
Chicago has an excellent music scene, and Sofar Sounds is a platform connecting local artists with non-traditional venues for intimate sets. See if there's any shows during your visit, but be prepared to sit on the floor!
Steppenwolf Theatre Company
One of the premier theaters in town, and David's personal favorite since falling for a membership sales pitch years ago. Worth a visit if anything running catches your interest.
Snakes & Lattes Chicago
Fall in love with a new board game or enjoy an old favorite at this board game lounge. Food and beverage served up while you play. Family friendly.
Fox In A Box Escape Room Chicago
Actually fun escape rooms for those who love a puzzle. 10+ y/o options available.
Trickery
Charming and hilarious storefront magic show. Adult humor influenced by location in famously LGBTQ+ neighborhood Northalsted. Other options for magic are Chicago Magic Parlour downtown, and Chicago Magic Lounge in the Uptown neighborhood.
Puttery
Elaborate indoor minigolf course in the trendy Fulton Market district. Family friendly at certain times.
Duneyrr Fermenta Winery and Brewery
Tasting room specializing in natural wines, ciders, and beers.
Arbella
For those of us who must spend $20 on a cocktail, this is your spot - Smokey's Sidepiece is a personal favorite.