Chicago on the Cheap

Ice skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago’s Sky Rink, perched above the Magnificent Mile with sparkling lights and pine trees. The rink is open through February 16, 2026. Ride up to the fourth floor of […]

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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 diversified events, so choose your favorite.  Some events may […]

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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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