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Destinations

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BEST Things to Do in Chicago in January 2027 (From a Local!)

Posted on November 2, 2026 by savvyglobetrotter
outdoor ice skating

Searching for what to do in Chicago this January? Here are the best things to do in Chicago in January 2027 (from a local) – from fun outdoor winter activities to the best indoor events and attractions. I suggest bookmarking… Continue Reading →

Destinations
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Most Romantic Things to Do in Chicago for Couples (2026)

Posted on November 2, 2026 by savvyglobetrotter
fireworks in Chicago at night

The most romantic things to do in Chicago for couples in 2026. Whether planning a weekend getaway in the city with your significant other or looking for unique Chicago date night ideas, these are the best activities to enjoy in… Continue Reading →

Destinations
3

The BEST Time to Visit Chicago: 2026/2027 Month-by-Month Guide

Posted on November 2, 2026 by savvyglobetrotter
The best time of the year to visit Chicago

Not sure what is the best time to visit Chicago? I have lived in Chicago for most of my life so I’ve put together an updated month by month guide to help you figure out the best time to go… Continue Reading →

Destinations Chicago
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30 BEST Indoor Things to Do in Chicago on a Cold or Rainy Day (2026)

Posted on November 2, 2026 by savvyglobetrotter
The Art Institute of Chicago

Looking for indoor things to do in Chicago on a cold or rainy day? I have put together the ultimate list of the best indoor activities in Chicago in 2026. Best Indoor Activities in Chicago These are the best indoor… Continue Reading →

Destinations
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BEST Things do in Chicago for Thanksgiving Weekend 2026

Posted on November 2, 2026 by savvyglobetrotter
Christkindlmarket Chicago

Spending Thanksgiving in Chicago and looking for fun things to do other than eat turkey? You are in luck because Thanksgiving is a great time to visit Chicago. There are tons of things to do in Chicago on Thanksgiving Day (November… Continue Reading →

Destinations
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Best Things to Do in Chicago This November

Posted on November 1, 2026 by savvyglobetrotter
Chicago Riverwalk in the fall

Are you searching for what to do in Chicago this November? Here are the best things to do in Chicago in November 2026 (from a local) including the best November 2026 events and the top activities and attractions. I suggest bookmarking… Continue Reading →

Destinations, Travel Tips
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BEST Things to Do in Chicago in December 2026 (From a Local!)

Posted on November 1, 2026 by savvyglobetrotter
City of Chicago Christmas Tree

Searching for what to do in Chicago this December? Here are the best things to do in Chicago in December 2026 (from a local) – from the top attractions to festive holiday events and activities. December is one of the best… Continue Reading →

Destinations Chicago
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BEST Things to Do in Chicago in November 2026 (From a Local!)

Posted on October 30, 2026 by savvyglobetrotter
Chicago Riverwalk in the fall

Are you searching for what to do in Chicago this November? Here are the best things to do in Chicago in November 2026 (from a local) including the best November 2026 events and the top activities and attractions. I suggest bookmarking… Continue Reading →

Destinations Chicago
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BEST Things to do in Chicago at Night

Posted on October 30, 2026 by savvyglobetrotter
Chicago Riverwalk at night

Looking for fun things to do in Chicago tonight? Below are the best things to do in Chicago at night. Whether you are visiting Chicago or have lived here all your life, you will find something unique and new to… Continue Reading →

Destinations
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Christmas Towns Near Chicago for a Festive Holiday Getaway

Posted on October 2, 2026 by savvyglobetrotter
photo of reindeer during Christmas on a reindeer farm near Chicago

The best Christmas towns near Chicago. Get in the holiday spirit with these festive Christmas getaways near Chicago. Christmas Getaways from Chicago Looking for the best Christmas getaways from Chicago? Although there is so much to do during the Christmas… Continue Reading →

Destinations

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