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 … [Read More...]
Latest Deals and Events

Free and cheap things to do this weekend in Chicago
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 … [Read More...]

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 … [Read More...]

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 … [Read More...]

Chicago Artisan Market
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 … [Read More...]

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: … [Read More...]

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 … [Read More...]

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 … [Read More...]

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 … [Read More...]
Today’s Free & Cheap Events in Chicago
Featured Events

Free and cheap things to do this weekend in Chicago
Looking for something fun to do this weekend in Chicago? There are tons of free and cheap events in the city. Here’s … [Read More...]

Get Free Stuff on Your Birthday
It's your special day so you deserve a gift. Lots of companies offer free stuff for your birthday. In some cases, … [Read More...]

Free or cheap things to do in Chicago this week
If you’re looking for a way to entertain yourself, your family and your friends in Chicago without spending a lot of … [Read More...]

Peggy Notebaert Nature Museum Free Days
Peggy Notebaert Nature Museum Free Days Where: Peggy Notebaert Nature Museum, 2430 North Cannon Drive, … [Read More...]













Chicago on the Cheap is a member of Living on the Cheap, a network of websites published by frugalistas, journalists and consumer advocates. Find practical advice on saving money on groceries, travel and shopping, plus tips from our experts on how to live the good life for less at 