Curated Activities – Chicago Day Tours

Old Town Chicago Food Tour

A women holds a platter of Chicago style hot dogs.

When thinking about food in Chicago, deep dish pizza is a given, but how about adding in French, Lebanese, spice samples, fudge and tea? Chicago has them all. A must-do of Chicago day tours. We are jealous of you just writing this. – by Viator

Chicago River Architecture Cruise

Tall buildings in Chicago along the river.

Frank Lloyd Wright hails from Illinois and his influence on the Chicago skyline, and architecture in general, remains to this day. See distinctive buildings, sculptures and landmarks on this peaceful ride. One the best Chicago day tours. – by Viator.

Bike the Lake Front and Rush Street

Tourists jump and celebrate while talking a bike tour in Chicago.

Lake Michigan’s coast offers miles and miles of running and biking trails. Ride along the shore as you experience a slower-paced view of the city. You’ll pass by the Lincoln Zoo, the Museum of Contemporary Art and make stops at North Beach and Lakefront Trail. – by Viator

Donuts Galore

A man holds a pink donut.

Blustery Chicago is a food city and very much a donut city. It’s that early morning hustle and bustle vibe. This tour visits 4 iconic donut shops with generous tastes included. Walking between stops lessens the calories! – by Underground Donut Tour

Chicago Ghosts and Gangsters

Al Capone in a fedora.

Al Capone ruled Chicago during Prohibition. Enjoy this walking tour of speakeasies and side streets as your guide shares the lively story of gangland Chicago. Add in the ghosts of Palmer House and a riverwalk stroll. Knowledgeable guides will advise on where to eat lunch or dinner at a real speakeasy with a trapdoor! – by Viator.

I miss everything about Chicago, except January and February.” – Gary Cole

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