School’s out, vacation is here, and visitors are pouring into Chicago to take advantage of our world-class institutions, fine dining, and great shopping. So, if you’re out and about this season, where should you go? Here’s our quick guide to the best things to do this winter.

1. Chicago Museums – Winter is a great time to be at one of our amazing cultural institutions. Not only are free days featured during these colder months, new exhibits can open up new worlds for people of all ages. Among our favorites right now: the “Christmas Around the World and Holidays of Light” at the Museum of Science and Industry, and “China’s First Emperor and His Terracotta Warriors” at the Field Museum.

2. Chicago Trolley Holiday Lights Tour – You’ve seen the trolleys around downtown, taking visitors to Chicago’s best tourist destinations. But during the Christmas season, Chicago Trolley and Double Decker Bus Co. offers a 2.5 hour tour that stops at Sprinkles for cupcakes, the Christkindlmarket for shopping, and visits ZooLights at Lincoln Park Zoo. For information and pricing, visit the Chicago Trolley website.

3. Ice Skating – Downtown, two of the most iconic places to skate are the McCormick-Tribune rink at Millennium Park and the Maggie Daley Skating Ribbon. But park rinks exist all over the city, including Lincoln Park Zoo. Often, the rinks are free, but skate rental costs money, so be prepared.

4. Chicago Breweries – Chicago’s beer scene continues to grow and diversify. Visit tap rooms around town for a warming drink, enjoy bar food, and take tours of brewery operations. From the more established Goose Island to new and exciting companies like Baderbrau, there’s something for everyone. Visit the Illinois Craft Brewers Guild as a starting point.

5. Navy Pier – Enjoy restaurants, the food court, performances at the Chicago Shakespeare Theatre (“King Charles III” plays through 1/15), and dinner cruises all in one location. This is a great place to spend some time with family. Shop for Chicago treasures, come for weekend festivals and trade shows, and enjoy an IMAX movie.

6. Shopping on the Mag Mile – An outing along Michigan Avenue includes world-class shopping and an amazing selection of restaurants, along with great people-watching. Whenever you’re cold, duck into a shop and spend some money – or just window-shop. Either way, a day here is great retail therapy and a lot of fun.

7. Sporting EventsThe Bears play a couple of times over Winter Break, the Blackhawks are at home for a few games, and the Bulls are in town too. The Chicago Wolves AHL hockey team in Rosemont is around for part of the holiday as well. Even if you don’t want to see a full football game in the cold, you can visit one of the area’s sports bars and restaurants to gather with friends and watch.

8. Rosemont – Near O’Hare International Airport, this suburb offers great hotels, interesting eateries, nightlife and entertainment, and more. The Fashion Outlets of Chicago are nearby if you like discount shopping, and MB Financial Park at Rosemont is one of our favorite spots for eating, skating, and making winter more festive.

9. Dining – Well, eating in Chicago is always pretty stellar. During the summer, we get sidewalk patios and great weather. This time of year, though, we like cozy and warm places with hearty meals. Chicago has great steak, thanks to its stockyard history – try Morton’s the Steakhouse. Chicago pizza is also a crowd-pleaser for winters like these. There are so many great places for pizza, but one of our favorites is Pizano’s.

10. CityPASS – Vacationing in Chicago can get pricey, which is why CityPASS exists. Your Chicago CityPASS allows you to get into five iconic destinations for a discounted price – $98 for adults, $82 for children. And it isn’t just general admission. You get to enjoy VIP perks, including special exhibits and fast passes. Visit the Shedd Aquarium, Skydeck Chicago, the Field Museum, the Museum of Science and Industry OR 360 Chicago, and the Adler Planetarium OR the Art Institute of Chicago (that’s a hard decision). Get yours at


Subscribe to our newsletter

Subscribe to our monthly newsletter to receive latest updates and other promotional offers.
Give it a try, you can unsubscribe anytime.