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
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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
Popeyes offers $5 Faves Menu with four popular choices
Popeyes is starting off the year strong with lots of value for diners on a budget. The new limited-time value menu makes it easier for customers to enjoy the popular chicken restaurant’s bold flavors without breaking the bank. Photo: Popeyes From Jan. 5 to Feb. 15, 2026, … [Read more...] about Popeyes offers $5 Faves Menu with four popular choices
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
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
