Chicago winters are long, cold and windy, and many people treat them as something to wait out. That misses a lot. From mid-November through early March the city offers outdoor skating with skyline views, holiday markets, light shows and a set of warm indoor places that feel even better when it is freezing outside. This guide covers the best winter outings and how to plan for the weather.
Key takeaways
- The Maggie Daley Park skating ribbon is free to use in season; skate rentals cost extra.
- Christkindlmarket at Daley Plaza is free to enter and runs from late November to Christmas Eve.
- The conservatories and many museums make excellent cold-day escapes.
Outdoor skating
The skating ribbon at Maggie Daley Park is a looping ice trail that winds past the climbing walls with the skyline behind it. Admission is free and skate rentals cost extra. The season usually runs from mid-November into early March, depending on the weather. Many neighborhood parks and suburbs also open outdoor rinks when it is cold enough; check your local park district.
Holiday markets and lights
Christkindlmarket, a German-style holiday market, sets up at Daley Plaza in the Loop each year. Entry is free, and the market runs from late November through December 24 with food, drinks and gifts. Organizers also run markets in other locations; check their website for this year’s sites and dates.
ZooLights at Lincoln Park Zoo fills the zoo with light displays in the evenings from late November into early January. Tickets are needed, with some free nights that still require a reservation. In the suburbs, the Morton Arboretum hosts a ticketed winter light show along its trails.
Warm indoor escapes
The Garfield Park Conservatory and the Lincoln Park Conservatory keep their glass houses warm and green all winter, and their holiday flower shows are popular. Both usually need timed reservations. Many museums schedule free days for Illinois residents in the winter months, which makes January and February good times to visit. The Chicago Cultural Center, free and downtown, is another warm stop.
Winter outings compared
| Outdoor skating | Markets and lights | Indoor escapes | |
|---|---|---|---|
| Cost | Free entry; rentals extra | Markets free; light shows ticketed | Free to moderate |
| Best time | Weekday evenings, sunny afternoons | Late November to December | Coldest days, January and February |
| Best for | Active outings, date nights | Holiday mood, families | Kids, rainy or bitterly cold days |
| Weather risk | Warm spells can close rinks | Crowds on weekends | Low |
Tip: Dress for the wind, not just the temperature. Near the lake, wind chill can make a mild day feel much colder. Layers, a hat that covers your ears and waterproof boots make outdoor outings far more pleasant.
Winter in the suburbs and beyond
Forest preserves across the region stay open for winter walks, and some offer cross-country skiing or snowshoeing when there is enough snow. Further out, the frozen waterfalls at Starved Rock State Park are a striking sight after a long cold spell, though trails can be icy. Galena’s historic downtown is decorated for the holidays and makes a cozy winter getaway.
Which winter outing fits your day
Go skating if
- It is cold but clear.
- You want something active and free.
Go to a market or light show if
- It is late November or December.
- You want a festive outing with family or friends.
Head indoors if
- It is bitterly cold, snowing hard or raining.
- You have young children.
Before you go
- Check whether rinks are open; warm spells and heavy snow can close them.
- Reserve timed tickets for light shows and conservatories.
- Look up winter free days at the museums you want to visit.
- Allow extra travel time; snow slows everything down.
Winter with kids
Children often handle the cold better than adults, as long as the outing is short and active. Pair a skating session with a warm stop nearby, such as the Chicago Cultural Center or a museum. Lincoln Park Zoo is open every day of the year, and its indoor animal houses are a good break on a chilly afternoon. Bring a change of socks and gloves; wet hands and feet end outings faster than low temperatures.
Common mistakes
The most common mistake is visiting the holiday market on a December Saturday evening and spending most of the time in line. Weekday afternoons are much calmer. Another mistake is not checking conditions before driving to a frozen-waterfall hike; icy trails can be closed.
Frequently asked questions
Is skating free in Chicago?
Entry to the Maggie Daley Park skating ribbon is free. Skate rentals cost extra.
When does Christkindlmarket open?
The Daley Plaza market usually opens in late November and runs through December 24. Check the official website for this year’s dates.
What can I do in Chicago on a very cold day?
Visit a conservatory, a museum on a resident free day, or the Chicago Cultural Center.
For more on the skating ribbon, see Millennium Park and Maggie Daley Park: One Walk, Two Very Different Parks. For the warmest winter escape, read Garfield Park Conservatory vs. Lincoln Park Conservatory.