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Chicago Must Do
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items They don't call it the Windy City for nothing! Yes, it can be cold and windy in the winter months but Chicago is also a city filled with great history, food and plenty of things to do. Here are some of my favorites
I'm always a fan of food tours to ensure you don't miss out on the local delights!
THE TOP 10 Chicago Food Tours To Try in 2024 - Viator
One of my favorite pizza places - and the name… forget it! I'm in Love!
Pie Hole Pizza Joint : Lakeview
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With day or night options - head here for a river cruise you will not forget! (Unless you have too many cocktails of course…..)
Chicago River Cocktail Cruise by Day or Night 2024
Explore the incredible architecture of Chicago with this river cruise
Chicago River Architecture Cruise History and Sightseeing Tour 2025
If architecture is your thing - check out this tour where you will get to see some of the intricate details not typically seen by the public.
Chicago's Secret Interiors Architectural Walking Tour
With a historian as your guide, you’ll step back to the Roaring Twenties, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone
Chicago: Gangsters and Ghosts Walking Tour
Head here to see incredible 360 views of the Chicago skyline as well as Lake Michigan
360 Chicago Observation Deck Admission Ticket 2025 - Viator
Learn the history and architectural heritage of Chicago on tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower
Chicago River 45-Minute Architecture Tour from ... - Viator
If you are a baseball fan, this is the tour for you! Learn the history behind this American Icon
Tours of Wrigley Field | Chicago Cubs - MLB.com
Craving authentic Italian? Head here!
RPM Italian
This family friendly museum is home to the most complete T Rex ever discovered!
Field Museum of Natural History Admission Tickets - Chicago - Viator
Looking to let out a little steam? This is a family friendly activity everyone will enjoy!
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago - Viator
Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out
Chicago Crime and Mob Bus Tour - Viator
This is the highest point in the city where you can enjoy 360 views of this magnificant skyline
Chicago Skydeck
I've been to the Museum of Ice Cream in Singapore and I can tell you - it's a ton of fun and you will leave with a belly full of ice cream!!
Chicago: Museum of Ice Cream Admission 2024 - Viator
Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge
Medieval Torture Museum Ticket with Audio Guide and ...