Here’s How To Unwind Off The Clock In Chicago

Got a business trip to Chicago on the books? If so, you’re in luck - the Windy City has no shortage of lively things to do. It’s the perfect place to enjoy an extended weekend of bleisure or just to make the most of your evenings after work. Here’s how to have a great time in Chicago when you’re off the clock.

Chicago After Work Business Trip Ideas

Catch some live music.

Chicago is famous for its blues and jazz scenes dating back to the early twentieth century. Pop into a jazz bar for great beer, great tunes, and laidback locals who live up to their reputation for Midwestern friendliness.


Check out a Cubs game.

Chicago is a baseball fan’s dream, but even if you’re not very into the sport, the energetic atmosphere of game day is too much fun to miss. Whether you catch the game in a legendary sports bar like The Cubby Bear or Sluggers, or you go the extra mile by snagging a ticket to Wrigley Field, you’ll be glad you did.


Take in some world class art.

The Art Institute of Chicago is home to famous works like American Gothic, Nighthawks, Vincent Van Gogh’s The Bedroom, and Sunday Afternoon on the Island of la Grande Jatte 1886, perhaps better known as the painting from Ferris Bueller’s Day Off. Spend an afternoon getting lost in the archives.


Treat yourself to a top-notch dinner.

Chicago’s culinary scene offers delicious dishes on every end of the spectrum, from delightfully divey to Michelin starred. If you’re looking to treat yourself to a high-end dinner, the options won’t disappoint. Sepia, set in a former 1800s print shop, celebrates Chicago’s unique history with tasty American cuisine. Topolobampo offers high-end Mexican dishes and a fantastic atmosphere. Next, a James Beard award winner, pushes the envelope by completely switching up its menu every four months. Be sure to make reservations in advance!

What to do in Chicago after Business Trip

Hit the beach.

Chicago sits on the shore of Lake Michigan, and this beautiful blue behemoth looks a lot more like a miniature ocean than the stagnant neighborhood lake you swam in growing up. In the summertime, the beach comes alive with waterfront bars, mellow waves, and ample space for sunbathing.


Chow down on Chicago style pizza.

Chicago’s famous deep dish pizza is a must-try, but you’ll want to bypass touristy spots along Michigan Avenue where you’ll wait in line for hours. Instead, drop by a local establishment like Burt’s Place or Pequod’s Pizza to try deep dish in its most delicious form.


Take in an architecture tour.

Chicago’s architecture is one of a kind, and the Chicago Architecture Foundation keeps each building’s stories alive with walking tours and boat tours. The tours bring a whole new life and context to famous architectural spots like the Willis Tower, the Tribune Tower, and many others that have stood the test of time. Be sure to pack your camera for this one.

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