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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

Small map
Click to view the full map.

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.

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.

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.

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.

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.).

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.).

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.).

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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