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 … [Read more...] about New Year’s Rockin’ Eve in Chicago
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Kids eat free at IHOP in December
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 … [Read more...] about Kids eat free at IHOP in December
Pre-Kwanzaa Celebration and Marketplace
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 … [Read more...] about Pre-Kwanzaa Celebration and Marketplace
Music Box Annual Christmas Sing A long
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 … [Read more...] about Music Box Annual Christmas Sing A long
Skate in the Clouds at Peninsula Sky Rink
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 … [Read more...] about Skate in the Clouds at Peninsula Sky Rink
Shake Shack offers free Shack Sandwich every week in December
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 … [Read more...] about Shake Shack offers free Shack Sandwich every week in December
Free Sauced Night Market
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 … [Read more...] about Free Sauced Night Market
Sonic Drive-In offers 12 days of holiday deals in December
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 … [Read more...] about Sonic Drive-In offers 12 days of holiday deals in December
Ride the CTA Holiday Train
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 … [Read more...] about Ride the CTA Holiday Train
Hyde Park Handmade Artisan Bazaar
For ten years, the free Hyde Park Handmade Artisan Bazaar has supplied a monthly pop-up of hand-crafted goodies beloved by loyal customers. Don't miss the fun at the 2025 fall and winter dates on September 21, October 19, November 23 and December 21. This eclectic indoor … [Read more...] about Hyde Park Handmade Artisan Bazaar
Chipotle offers buy-one-get-one free entrée on Saturdays in December
Enjoy a frugal feast at Chipotle on weekends in December! The popular restaurant is making the holiday season a little merrier for Chipotle fans and diners on a budget alike. Take a break from running errands on Saturday to stop by Chipotle for a discounted dinner. And, if you’re dining alone, … [Read more...] about Chipotle offers buy-one-get-one free entrée on Saturdays in December
Popeyes’ new $20 Family Meal brings value and easy prep to dining table
Get ready to make a Popeyes run this holiday season! The popular restaurant is giving busy, frugal families two big gifts this season — a break from cooking (time!) and savings. Through Jan. 4, 2026, customers can unwrap the restaurant’s new Popeyes Family Meal — a feast that brings big value and … [Read more...] about Popeyes’ new $20 Family Meal brings value and easy prep to dining table
