Amazing Winter Activities to do in Chicago

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Over the holiday season, Chicago becomes a winter wonderland with beautiful Christmas lights, amazing sledding slopes, live music, and ice skating. These classic and well-known activities, along with a full-fledged holiday spectacle in the town square where you can enjoy free shows of holiday movies and of course meet Santa Claus. For the best Christmas vibes, party on wheels with a rental limo or party bus rentals is a great idea. Take a look at some of the top winter activities in Chicago.

Midway Plaisance Ice Rink

It is a family-friendly place that offers skating lessons, pick-up hockey games, and hosts seasonal events. You can book limo bus rentals to this place and level up the fun. This park area is located in the University of Chicago campus, where the first Ferris wheel was erected during the Chicago World’s Fair in 1893. The park also has a warming facility. Have a temporary escape from the cold and warm yourself before returning outside to have more snowy fun doing ice skating in Chicago.

In addition, Midway Plaisance hosts a variety of exciting special events throughout the year. Such as summer concert series, movie screenings, and the annual Silver Skates Speed Skating Competition.

Sledding Hill at Soldier Field

Soldier Field The 33-foot, lightning-fast slope of Sledding Hill is perfect for thrill-seeking sled riders. The park staff uses snow machines to ensure the hill is perfectly covered, even when it’s warmer outside, and the other city has melted. Before you roar down the slopes at heart-pounding speeds, you may take a panoramic view of Lake Michigan from the top of the hill.

Sky Rink on the Peninsula

When exploring top places to visit in Chicago with limousine travel, don’t miss the Sky Rink on the Peninsula. This rink offers amazing views of the city skyline surrounded by exquisite lights and is located above a 4-star hotel in the center of the action along Michigan Avenue. The skating rink is built on the terrace of the fourth story and has displays of the Chicago winter lights festival and Chritsmas trees. The skating isn’t the only thing to do here; you can visit an outdoor chalet serving warming treats like beignets and mulled wine.

Willis Tower

The best winter activities in Chicago can be explored in the indoor ambience. What is better than going to Chicago’s most recognizable (and tallest) structure, the Willis Tower, one of the city’s top winter attractions? Take the elevator to the highest floor for a breathtaking glimpse of those lovely city skylines!

Drink Cocktails in Rooftop Bars

A rooftop bar is one of the best options to drink cocktails and make your party memorable. With cozy fire pits and outdoor dining options, stay cozy while enjoying Chicago’s bar and restaurant delecacies. A rooftop ice skating rink, a pop-up with a winter wonderland motif, and private igloos that make you feel like you’re in a magical snow globe are just a few of the most memorable experiences here. Choose a right party bus size as per your friend circle and have fun!

The Chicago Winterfest

Attending the annual Winterfest is the most exciting and enjoyable winter activities in Chicago for both tourists and locals. An outdoor activities and indoor event that promises exciting fun activities for the whole family, including performances, arcade games, and an ice rink. Additionally, there are many food stalls where you enjoy native Chicago cuisine. So be sure not to miss this festival attraction on your Christmas week.

Some Exciting Free Things To Do In Chicago

If you are on a budget, there are various attractions, museums, and things to do in Chicago for free. Here is a list of some popular places to visit.

  • Clarke House Museum
  • Lakefront Trail
  • Chicago Riverwalk
  • Lincoln Park Conservatory
  • Lincoln Park Zoo
  • Newberry Library
  • Millennium Park
  • Navy Pier


There is no doubt that winter transforms Chicago into a tourism hotspot, and now that you know how much fun it will be. Make your travel more interesting by using our rental limo & buses. If you have some personal event plans in Chicago and want to book a ride, choose us without worry because we also offer customized birthday, nightout party and wedding transportation per your choice. Get to know the amenities available with every vehicle of our fleet individually. Make a call now!