Chicago is the place to be for Thanksgiving, with events leading right up to turkey time. The holiday kicks off with a massive parade. Then there’s the Turkey Trot, a pre-feast 5k run. If your head’s already at Christmastime, head over to the Christkindlmarket, an outdoor market where you can buy gifts or just hang out with a mug of mulled wine. And be sure to do some shopping in Wicker Park and Bucktown on Small Business Saturday, where local musicians will play live while you browse.

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November 18 - December 23 | Christmas market
Christkindlmarket
If your mind is already in December, step into Chicago’s largest open-air market for some good old-fashioned holiday cheer. The Christkindlmarket is inspired by those found in Germany, and it features nutcrackers, beer steins, ornaments, German sausages, beer, and mulled wine. This is a rare place that locals will brave the cold Chicago winters to visit—because it’s totally worth it.
Daley Plaza, Washington and Dearborn St., Chicago | Free | website

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November 24 | Parade
McDonald’s Thanksgiving Parade
Chicago’s Thanksgiving parade is the second-largest in the nation, and it’s been going strong since the 1930s. Expect special guests (politicians, Broadway stars, and celebrities) representing every part of the country and the world. This year, the Harlem Globetrotters, the Black Ensemble Theater, and Ronald McDonald will all be in attendance.
8:00 AM - 11:00 AM | State St. btw. Congress Pkwy. and Randolph St., Chicago | Free | website

November 24 | 5k race
Turkey Trot
One of Chicago’s longest-running traditions, the Turkey Trot 5k race is also a great way to burn off some calories before you eat the biggest meal of the year. Choose to run, jog, or walk the 5k or the 8k before doing turkey bowling, corn hole, and a football toss in the Turkey Tailgate Zone while sipping warm apple cider. Bring the kids along, and they can do the Plymouth Rock Ramble Kids Race.
9:00 AM | 2610 N. Canon Dr., Chicago | From $35 | website

Christkindlmarket

November 26 | Music festival
ChillFest Acoustic Musical Festival
On Small Business Saturday (where, in contrast to Black Friday and Cyber Monday, you get out and shop to support small businesses), the Wicker Park Bucktown Chamber of Commerce celebrates more than 60 local musicians by having them perform in 20 neighborhood storefronts. The ChillFest Acoustic Music Festival combines the spirit of a music festival with holiday shopping, all the while encouraging consumers to shop at local small businesses and boutiques in Wicker Park and Bucktown. Featured musicians include pop-folk duo Future Stuff and female hip-hop artist Pinqy Ring.
2:00 PM - 6:00 PM | Locations vary | Free | website

November 26 - 27 | Escape the city
Hocking Hills, Ohio
While most visitors head here for the scenic summer hiking terrain, late fall and winter are an even better time to visit. There are fewer crowds to block your view of rock formations and caves, and the snow adds a layer of magic to the outdoors. Settle in at the Glenlaurel Inn & Spa, where you can stay in a Scottish-themed cottage (ask for one with a hot tub). The restaurant is the highlight there, with a six-course menu nightly and seven courses on Saturdays.

Danielle Braff lives in Chicago with her husband, two daughters, two cats, and her dog. When she’s not writing, she’s out photographing her city and running around frantically trying to fit as many events as she can into her day. You can check out her other articles at Daniellebraff.com.

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