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Top 10 Winter Activities in Chicago

Updated: Nov 18, 2019

It is no secret that the winters in Chicago can be brutal. The good news is that you can still have a great time when it's chilly outside. We have compiled the following list of outdoor and indoor activities.


1) Skating Rinks

It is truly a lovely scene when the two ice rinks open up in Chicago. McCormick Tribune Ice Rink is situated in Millennium Park and is free! You do have to pay for skate rentals but it is worth it. If you do not know how to skate, the rink offers free lessons during the weekends, so no excuses for not going! Maggie Daley Park Skating Ribbon is another beautiful skating venue that offers beautiful views in the heart of Chicago’s downtown. It is actually very close to McCormick Tribune, so should one rink be crowded, make sure to check out the other option. Maggie Daley Park offers a little more adventure since it is laid out as a path rather than just an open rink. Just like McCormick Tribune, Maggie Daley is also free with a small cost for skate rentals.

2) Festivals

Festivals in Chicago happen year-round so make sure to look into your neighborhood’s schedule since there are plenty to plan for in Chicago. Two great holiday festivals we would recommend is Chicago Magnificent Mile Lights Festival (Nov 22-23) and Winter Wonderfest at Navy Pier (Dec 6 – Jan 12). The Lights Festival starts off in Pioneer Court (401 N Michigan Ave) on Friday and is filled with live music and fun activities that carry over to Saturday - which is when the parade takes place. The finale is a beautiful lighting ceremony and a great display of fireworks! Navy Pier’s Winter Wonderfest is located in the Festival Hall. The hall is literally transformed into the North Pole (assuming the North Pole is a real place :-p). On a positive note, a Winter Wonderfest actually does exist and could be visited during the winter in Navy Pier!

3) Sledding

We do not care how old you are, sledding is still fun regardless of your age and it could be done in downtown Chicago during the winters! Our two notable mentions are Soldier Field (South Loop) and Montgomery Ward Park (River North). The only two things you need to bring to these hills is a pair of warm-water-resistant clothes and a sled. Soldier Field offers a 33-foot vertical drop which will make sledding here far more exciting than watching a Bears game. Montgomery Ward is also a great place to enjoy a low-key day of sledding. It is located right next to the Chicago River in the River North area – so make sure to enjoy and avoid the river. You do not want to end up in the river – in the winter or in the summer.

These last two activities will require a little driving to Wisconsin because they will not be found in the Chicagoland area. You can easily rent a car at the nearest rental car facility and take the drive.

4) Ski Resorts

If you are a skier/snowboarder and moving to Chicago, you will find out that there are no ski resorts here. We wanted to bring up two options that are less than a 2-hour drive away. Anything more than 2-hours can get tough, especially if you’re planning a day trip to a ski resort. Wilmot Mountain Ski Resort is the closest ski resort to Chicago that offers a decent level of runs and has ski rentals. It also offers an area for tubing and a revamped base which makes it a good place to ski or snowboard. Alpine Valley Resort is another spot that will put you at about a 2-hour drive from Chicago. Alpine also offers decent runs and rentals, which makes it a suitable place to visit especially for a day trip. There are larger ski resorts that are 3-4 hours of a drive away, but at that point it is a personal preference of whether it makes more sense to fly out to ski in an actual mountain versus driving 4 hours in the Midwest to ski/snowboard.

5) Ice Castles

Ice Castles in Lake Geneva, WI is definitely a site to see. This is still an outdoor type activity so it is recommended that you bring warm clothes and boots to make this experience enjoyable. The castle is very large with many rooms and the place does a great job with the lighting and music. Some people do prefer to go at night since you are able to experience the full affect of the lighting. Again, it may not be worth a 2-hour drive just to see this, but if you are going skiing/snowboarding in the area for the weekend, we recommend to visit this place.


1) Chicago Theaters

If you want to do something indoors in the winter which you would normally not do during the summer time, try attending some of the theater performances in Chicago. There are some great shows performed by top-notch talent. Research the schedules at the Goodman Theatre, Steppenwolf Theatre, Chicago Shakespeare Theater to see if there’s anything that might entertain you. The Chicago Lyric Opera is another beautiful venue filled with plays and musical performances. For the holidays, make sure to catch Joffrey Ballet’s “The Nutcracker”!

2) Indoor Leagues

If you enjoy competitive or recreational sports, make sure to check out Players Sports & Social Group as well as Chicago Sport & Social Club. Between these two organizations, you will find plenty of options for nearly any indoor sport that is of interest to you. This is a perfect way of meeting people, enjoying the sports you love, and keeping active while the outside world freezes around you. We highly recommend visiting the websites of these two clubs – you will see the type of sports available and enrollment dates. The people who join are absolutely wonderful and friendly and it is the people who continue to make these indoor leagues something you need to try!

3) NBA and NHL Games

Catching a Bulls game or a Blackhawks game is always fun. Both teams play in the United Center which has undergone an expansion/renovation recently. This is a great indoor facility where you can enjoy the games in a warm environment. You may be wondering about the Chicago Bears. Well, not only is this more of an outdoor activity, usually at around the time the winter comes to Chicago, their season is pretty much over. Also, there are some good NCAA games to catch, so if this is something that interests you, check out the team sites of Loyola University and DePaul University.

4) Restaurant/Bars

The winter is the time for you to familiarize yourself with Chicago’s restaurants and bars. Check out Soloma’s Top 10 for restaurant/bars in River North, West Loop, and other neighborhoods. You may even come across something not on the list that very few know about. It’s a very rewarding experience to find something that happens to be terrific but has little media attention. It is fun impressing friends by introducing them to “a spot” you know about. This is one of the many great things about Chicago – the options of excellent food and bars are endless. If you’ve waited this long to scout for new places, doing so in the winter is fun!

5) Gym

Hitting the gym is what many people do in Chicago – especially during the first two weeks of January after making unrealistic New Year’s resolutions. Gyms tend to get less crowded towards the end of January after people find ways to justify breaking their gym contracts along with their New Year’s resolutions. We are not going to list any gyms here but wanted to mention that you should always review the gym in the building you are about to lease or buy. Based on our clients’ experience, the gym is one of the more important amenities in their prospective homes. The ideal setup is not having to go out in the cold if your building has a great gym facility that you can walk into from your unit. If you’d like to know of luxury apartments with great gyms, please don’t hesitate to contact us!


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