Things to Do This Winter in Chicago: Outdoor Activities

Entry-level venues for winter sports, three mountains for great skiing, and a park-and-walk guide to winter fun around the Loop

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RELATED: Our calendar of things to do this winter—from December to February »

A Park-and-Walk Guide to Winter Jollies Around the Loop

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FOG THE GLASS
The holiday displays at Macy’s (1) (111 N. State St.) make a great place to start your day. If you park near the Art Institute (2) (111 S. Michigan Ave.), visit the museum’s Thorne Rooms; nine of the miniature dioramas have been decked in seasonal swag.

STALK SANTA
The Macy’s Claus mans his fifth-floor station daily during store hours from November 25 through December 24. You can also spy on Santa toiling away in his workshop, on the southwest corner of Christkindlmarket (3) in Daley Plaza (50 W. Washington St.); the hard-working fellow is there every day until at least 8 p.m. from November 23 through December 24.

GLIDE AROUND
We’re pretty sure there will be a line at the ice-skating rink on the 94th floor of the John Hancock building. So trek over to the McCormick Tribune Ice Rink (4) (Michigan Ave. at Washington St.; $10) or visit the equally affordable oval at Daley Bicentennial Plaza (5) (337 E. Randolph St.; $7) in Grant Park.

SING A FESTIVE TUNE
Chicago choral groups belt out holiday songs with Cloud Gate (6) looming behind them. Caribou Coffee (7) (20 N. Michigan Ave.) gives out warm drinks during the 50-minute sing-along that happens in Millennium Park every Friday at 6 p.m. from November 25 through December 16.

WARM YOUR HANDS
Ward off the chill with a piping-hot mug of coffee or cocoa at Intelligentsia (8) (53 E. Randolph St.), Starbucks (9) (202 N. Michigan Ave.), Argo Tea (10) (16 W. Randolph St.), Lavazza Espression (11) (27 W. Washington St.), or Café Descartes (12) (327 N. Michigan Ave.). Hot cider is served at Chicago’s Downtown Farmstand (13) (66 E. Randolph St.).

CATCH A BUZZ
Fight fatigue with sugar! Cupcakes abound at Magnolia Bakery (14) (108 N. State St.), Crumbs Bake Shop (15) (134 N. LaSalle St.), Sugar Bliss Cake Boutique (16) (115 N. Wabash Ave.), and Sarah’s Pastries & Candies (inside Macy’s, 111 N. State St.).

FIND RELIEF
The obvious public pit stops are the first- and second-floor bathrooms at the Chicago Cultural Center (17) (78 E. Washington St.) and the Jay Pritzker Pavilion (18) (201 E. Randolph St.). But seek out nicer amenities in the lobbies of the many Loop hotels, in particular theWit (19) (201 N. State St.), the Palmer House Hilton (20) (17 E. Monroe St.), and the Hard Rock Hotel (21) (230 N. Michigan Ave.).

CRANE YOUR NECK
Look north up Michigan Avenue to catch a glimpse of the lights along the Mag Mile. Where the el runs overhead—along Wabash Avenue and Lake, Van Buren, and Wells Streets—you might spot the wrapped-and-ribboned Christmas train jingling by.

 

Illustrations: John Kenzie

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2 years ago
Posted by BeautifulSnow

Living in Chicago & across the lake, I wait 10 months of the year for snow. I teach a lot of couples from Chicago how to ski along the lit trails of Lake Michigan. It's dirt cheap, even in my book! These are usually very cool ppl who take a weekend getaway. I recommend trying to ski at night on the lit groomed trails (or unlit trails if you dare) - it is so beautiful at night, esp if it is snowing, and less intimidating if you are new.

And thank you for the tips, a lot of ppl are clueless, so it is extra cool. Thank you my Chicago friends. You made ski instruction more fun last year.

1 year ago
Posted by Eliza

These are some great recommendations! They just don't seem to scratch the surface of our great city in the winter. I LOVE Intelligentsia and all the ice skating rinks. But if you've only got one day, I'd sneak in a little history too. I love the walking tours by Chicago Detours. I went on a few this summer, but they're mostly inside, so I'm sure they'd be great for the winter too.

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