Chicago on the Cheap

Enjoy all that’s jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier.  Slide, skate, ride and soak up holiday fun at this indoor fest from November 27, 2026, to January  3, 2027. Head to Navy Pier’s Festival Hall and take in the 420-foot holiday tree, twinkling lights and joyful […]

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Dive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor,  classic holiday movies and more at Winterland at Gallagher Way, November 20-December 31, 2026. Head to the Wrigleyville neighborhood to celebrate the season with a stroll through Winterland, including the Winter Market and […]

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Thank you for your service. Everyone wants to thank veterans and active military members for their courage and sacrifice. And many restaurants and businesses show their appreciation on Veterans Day with a FREE or discounted meal or service on Nov. 11, 2025. Living On The Cheap only includes deals and giveaways that we’ve independently verified. […]

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The beloved Chicago holiday tradition of lighting the City of Chicago Christmas tree that towers over Millennium Park will kick off on November 20, 2026. This live event will fill Millennium Park with music, fireworks and thousands of twinkling lights. A 53-foot-tall Colorado blue spruce was selected for this year’s Christmas tree, making it the […]

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Looking for something fun to do this weekend in Chicago? There are tons of free and cheap events in the city. Here’s our list of the top free events, discounts, and deals to have fun around town on your Friday, Saturday, and Sunday. There are many diverse events, so choose your favorite.  Some events may […]

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