Chicago on the Cheap

For the first time ever, the iconic Dick Clark’s New Year’s Rockin’ Eve will feature Chicago’s midnight countdown on the country’s most-watched New Year’s Eve Broadcast. Chicago will host the free New Year’s Eve countdown on the Chicago Riverwalk on December 31, 2025, kicking off at 7 pm. Witness the historic first Chicago New Year’s […]

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Parents are always looking for ways to stretch their budget. And this family-friendly offer from IHOP will definitely make families joyous and merry this holiday season. Take a break from shopping and take the kids to IHOP for a frugal feast because the little ones get to eat for FREE. Then, use the extra money […]

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Chicago celebrates the seven-day, African American holiday of Kwanzaa with performances, plays, story-times and festivals throughout the city. Head to the Washington Park refectory for a free day of music, cultural experiences and a marketplace with the Pre-Kwanzaa Holiday Celebration and Marketplace on December 20, 2025. Celebrate Umoja, the first Kwanzaa principle, which means unity, […]

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Celebrate the holiday season in the old school style with classic Christmas movies and a fun-filled sing-along. One of Chicago’s most unique holiday traditions is enjoying classic Hollywood holiday movies, singing along to the beloved tunes and accompanying a live organist to sing Christmas carols during the annual Music Box Christmas Sing-A-Long and Double Feature […]

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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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