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Five festive holiday tours to take in Chicago this season

Annalise Mantz
Written by
Annalise Mantz

In the middle of Chicago’s brutal winters—complete with single-digit wind chill, lake-effect snow and digging out your car—there’s one bright spot: the holidays. The Christmas lights, holiday markets and ice skating rinks that pop up all over the city bring some much needed yuletide cheer. Snow isn’t an inconvenience during the holidays—it just makes the city look even more magical.

This year, explore the winter wonderland of Chicago on a festive holiday tour. Whether you’ve been going to Christkindlmarket for years or it’s your first winter in Chicago, you’ll have a blast on one of these tours.

A Holiday Tour of Drinks, Daleys and Dead Guys

Explore Christmas past on this historical walking tour of iconic holiday landmarks in Chicago. As you walk to locations like the tree at the former Marshall Field’s Department Store, your guide will tell you some little-known facts, including how Mayor Richard J. Daley saved the Christmas Parade and why some say that Rudolf the Red-Nosed Reindeer was actually born in Chicago. Though you’ll be outside in the cold for most of the tour, you’ll stop inside local bars to warm up with a drink along the way.

Chicago Holiday Lights Tour by Segway

Zoom around Millennium Park and Daley Plaza in style on this segway tour. You’ll watch ice skaters flit around the rink, glide underneath the twinkling lights on Michigan Avenue and stop at Christkindlmarket for hot cocoa. Admire the city’s official Christmas tree before the tour ends and it’s time to turn in your wheels

Chicago Holiday Lights Tour

Don’t want to brave the elements? Stay warm and cozy inside a heated trolley on this guided tour of the holiday lights in downtown Chicago. Admire the festive decorations and twinkling light displays as your trolley makes its way toward Daley Plaza for a stop at Christkindlmarket. You’ll have an hour to spend sipping gluhwein, shopping for gifts and sampling the famous potato pancakes before it's time to head back to the trolley.

Chicago Holiday Stroll and Food Tour

It wouldn’t be the holiday season if you didn’t overindulge on sweets and booze. Why not do it while sightseeing on this food tour that stops at all the big holiday attractions? You’ll hit the rink at Millennium Park, the State Street lights and the Great Tree at Macy’s Walnut Room in between stops to taste the original brownies at the Parker House Hotel, deep dish pizza, traditional German fare and seasonal craft beers. Better come hungry!

Chicago Helicopter Holiday Lights Experience

Pro tip: If you’re planning a date in the next month or so, this helicopter tour works like a charm. You and your sweetheart will sip hot cocoa while waiting to board your chopper for a 20-minute ride over the city. In the air, you’ll fly over Lake Michigan toward the glowing cityscape. Spot Navy Pier, the Magnificent Mile, Willis Tower, Wrigley Field and even the Lincoln Park ZooLights festival before heading back to the heliport. It’s a once-in-a-lifetime experience that’s sure to sweep your special someone off their feet.

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