Chicago on the Cheap

Shake Shack is definitely making the holidays a little merrier for hungry bargain hunters! This December, the popular eatery is gifting customers a FREE Shack Sandwich — with a new burger or sandwich available every week. It’s the perfect excuse to take a “bargain break” from running holiday errands. Use the money saved on more […]

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Welcome the holiday season with shopping, food, music and vibes at Sauced Night Market, on December 12-13, 2025, at the Chicago Athletic Association downtown. This free roving market supplies over three dozen vendors selling hand-crafted artisan goods and food.  The holiday festivities include seasonal cocktails and lots of one-of-a-kind gifts for your Christmas list. Sip […]

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Kick off your holiday shopping experience and discover the best in Chicago’s handcrafted goods at the Chicago Artisan Market on December 14, 2025, in the West Loop. Shop for one-of-a-kind fashion, food, jewelry, art and home goods at this curated specialty marketplace. This flagship holiday market features special gifts and products you won’t see anywhere […]

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Sonic Drive-In is making the holidays jollier for hungry bargain hunters and fans alike!  For 12 days this holiday season, the popular restaurant is unwrapping a new daily deal with big savings — from December 8 to 19, 2025. Photo: Sonic Drive-In The daily deals are only available for MySonic Rewards members via the restaurant’s […]

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One of the things that makes the holidays in Chicago extra special is the CTA Holiday Train.   For 34 years, a festive train carrying Santa and his reindeer runs through all of the CTA lines, carrying joy and food baskets to Chicago community organizations. The train runs through December 22, 2025. See below for the […]

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