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Chicago Must Do

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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
 
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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
 
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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
 
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Explore the incredible architecture of Chicago with this river cruise
Chicago River Architecture Cruise History and Sightseeing Tour 2025
 
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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
 
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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
 
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Head here to see incredible 360 views of the Chicago skyline as well as Lake Michigan
360 Chicago Observation Deck Admission Ticket 2025 - Viator
 
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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
 
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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
 
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Craving authentic Italian?  Head here!
RPM Italian
 
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This family friendly museum is home to the most complete T Rex ever discovered!
Field Museum of Natural History Admission Tickets - Chicago - Viator
 
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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
 
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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
 
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This is the highest point in the city where you can enjoy 360 views of this magnificant skyline
Chicago Skydeck
 
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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
 
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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 ...