Please note: This “Know Before You Go” update is as of Jan. 22. Travel restrictions and requirements can change quickly, so be sure and check resort websites prior to travel.

So many choices, so little time. Living in the Chicago Metro region in winter may be cold and blustery, but that’s the idea of winter sports, right? We can ski or ride within a few hours’ drive time or we can head to O’Hare early in the morning and, if we hustle up I-70, be on world class Colorado ski slopes by the afternoon.

This year is more of a challenge with all of us taking COVID precautions. Use our guide to staying safe and healthy all winter without giving up the sports we love. invites all of our site visitors to choose their favorite ski resorts in a variety of categories each spring. Resorts listed in this guide are the top choices by Chicago site visitors.

Easy Day or Weekend Trips


Day trips are a breeze from Chicagoland. Just head north to Wisconsin or stick round a bit in Chestnut Mountain in Galena. You’ll generally find good conditions and a fun day or two on the slopes either way.

Face coverings required virtually everywhere at the resort except when eating or drinking and whenever social distancing is not possible.

OntheSnow Visitor Drive-To Picks


Chestnut Mountain: Drive time from Chicago is 3 hours.


Alpine Valley: Drive time from Chicago is 1.5 hours.

Cascade Mountain: Drive time from Chicago is 3 hours.

Christmas Mountain: Drive time from Chicago is 3 hours.

Devil’s Head: Drive time from Chicago is 3 hours.

Granite Peak: Drive time from Chicago is 3 hours.

Wilmot Mountain: Drive time from Chicago is 1.5 hours.


Ski Brule: Drive time from Chicago is 5.5 hours.

COVID Fast Facts – Day/Weekend Trips


Do I need to quarantine if I cross a state border?

There are currently no travel restrictions for travelling in Illinois, Wisconsin and Michigan.

When and where do I need to wear a face covering?

Masks mandatory in Illinois, Michigan and Wisconsin.

Where can I find the most up-to-date information or COVID guidelines?

Illinois: Masks mandatory statewide for those 2+. Restaurants/bars closed 11 p.m.-6 a.m. Tier 3 restrictions in place though Feb. 6.

Wisconsin: There is a stay-at-home order recommending - but not requiring - Wisconsinites to stay at home. Mandatory mask order in place for those 5+.
Walworth (Alpine Valley)
Columbia (Cascade Mountain)
Sauk (Christmas Mountain; Devil’s Head)
Marathon (Granite Peak)

Michigan: No indoor dining, nightclubs closed. Masks mandatory for those  5+ through Jan. 31.
Iron County (Ski Brule)

Destination Resort Fly-To Options


Check resorts for specific COVID restrictions.

OnTheSnow Visitor Picks: These are the most popular resort choices for those coming from the Chicago metro area.


Aspen Snowmass

Beaver Creek





Colorado COVID threat level: Amended and extended stay-at-home and safer-at-home orders depending on levels of risk in counties through Feb. 6.

Travel restrictions between Chicago and Colorado: None. Ski resorts open with some restrictions. Masks mandatory statewide for those 11+, in public spaces, public transportation & ride-hailing services. Pitkin County visitors (home to Aspen and other ski resorts) must sign a visitor affidavit and take test within 72 hours of arrival or quarantine for 14 days.


Big Sky

Montana COVID threat level:

Travel restrictions between Chicago and Montana: None. Mask mandate for those 5+ in indoor public spaces. Restrictions could vary on Native American reservations.


Park City Mountain Resort

Utah COVID threat level:

Travel restrictions between Chicago and Utah: None. Masks mandatory for those 2+.


Jackson Hole

Wyoming COVID threat level:

Travel restrictions between Chicago and Wyoming: None. Face coverings mandated through Jan. 25 for those 12+ in public spaces, or using public transportation and ride hailing services.

British Columbia, Canada

Whistler Blackcomb

British Columbia COVID threat level:

Avoid all non-essential travel. Mandatory negative COVID test for those 5+ 72 hours before flying into Canada. International travelers must self quarantine for 14 days and complete ArriveCAN application to enter Canada through Feb. 5.

Airline COVID Precautions


All airlines and airports have instigated stringent disinfectant procedures. Click below for your airline’s COVID page for specifics.
Air Canada

American Airlines

Delta Airlines

Frontier Airlines

Southwest Airlines

Spirit Airlines

United Airlines