Celebrate New Year's Eve in Chicago and avoid surge pricing and long waits for cabs on New Year's Eve night by hopping on a CTA train or bus for free. All CTA, Pace and Metra services will be free on December 31, 2025, starting at 10 pm. Join all the city's holiday festivities without … [Read more...] about Ride the CTA for free on New Year’s Eve
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Cheap Things to do in Chicago on New Year’s Eve
New Year's Eve in Chicago offers all the glamor and excitement expected on the last day of the year but all that glitz comes at a price. New Year's Eve events are notoriously expensive, whether you're just toasting the holiday with champagne or dancing the night away. If you don't want to pay the … [Read more...] about Cheap Things to do in Chicago on New Year’s Eve
Rudolph’s Rooftop
Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through January 25, 2026. Head to the … [Read more...] about Rudolph’s Rooftop
Free Kwanzaa Celebration at Malcolm X College
The exuberant seven-day African American tradition of Kwanzaa will be celebrated with seven days of free music, dance, culture and community at Malcolm X College on December 26, 2025-January 1, 2026. The annual Malcolm X College Kwanzaa Celebration honors the theme of … [Read more...] about Free Kwanzaa Celebration at Malcolm X College
New Year’s Eve Cruises from $20
Celebrate the new year on Lake Michigan with scenic views of the Chicago skyline, music and cocktails on New Year's Eve cruises with 312 Cruises on December 30-31, 2025. Sail away on a three-story luxury yacht with a full bar and dance floor for you to party the night away on the water. … [Read more...] about New Year’s Eve Cruises from $20
Burger King offers 13 Days of Deals (free food!) this holiday season
This holiday season, Burger King has a whopper of a gift for fans! Unwrap lots of delicious savings at the popular fast-food restaurant from Dec. 12 to 24, 2025. Each day, BK offers a FREE food item or beverage with a minimum purchase. Image: Burger King The offers are only … [Read more...] about Burger King offers 13 Days of Deals (free food!) this holiday season
Free Tuba Christmas at the Palmer House
Enjoy the sounds of the holiday on the biggest scale ever at the 52nd annual Tuba Christmas at the historic Palmer House Hotel on December 20, 2025. Tuba players from around the world will descend upon the Grand and State Ballroom in the Plamer House to perform a spirited concert of holiday … [Read more...] about Free Tuba Christmas at the Palmer House
New Year’s Rockin’ Eve in Chicago
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
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
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
