Update: Many Chicago holiday tours might be operating on a different schedule or on hold for 2020. Please contact tour operators directly for details and see our guide to the holidays in Chicago this year.
When Christmas comes around, Chicago lights up. There’s no shortage of glowing, glittering tours to take you around Chicago’s best holiday displays.
Here are seven ways to sightsee this season.
A festive food tour
Eat, drink, and walk your way through Christmas in Chicago. This holiday walking tour offered through Bobby’s Bike Hike hits all the indoor and outdoor highlights. Bring your appetite for samples of the famous Palmer House brownies, seasonal craft beer, and traditional German fare at Chicago’s famous Christmas market.
- Holiday Hike Tours are available daily, Nov. 18 – Dec. 24, 2019
Holiday tours by Segway
For the adventurous, these two-wheeled tours are the way to go. Step onto the futuristic, self-balancing ride and you’ll be zipping around Millennium Park in no time. Head over to the theatre district before hopping off to wander around Christkindlmarket.
- Holiday Lights Tour with Absolutely Chicago Segway Tours are available Wednesdays – Sundays, Nov. 21 – Dec. 21, 2019
Holiday dinner cruises
For unmatched views of the city horizon all lit up for the holidays, take an unforgettable dinner cruise along the lakefront or down the Chicago River. Step aboard these stunning ships for gourmet meals, top-shelf cocktails, dancing, live music, and plenty of holiday glitz.
- Lakefront holiday cruises by Spirit Cruises are available on select dates throughout December
- Lakefront and river cruises by Odyssey are available on select dates throughout December
- Lakefront holiday cruises by Mystic Blue are available on select dates throughout December
A historic holiday tour
A Holiday Tour of Drinks, Daleys and Dead Guys is a (mostly indoor) walking tour that explores both classic and off-the-beaten-path sites and stories. You’ll discover how Mayor Richard J. Daley saved the Christmas Parade, sip hot cocktails at a historic pub, see the official Chicago Christmas Tree in Millennium Park, and much more.
- A Holiday Tour of Drinks, Daleys and Dead Guys with Chicago Detours is available Nov. 22 – Dec. 29, 2019
Winter walking tours
Just because it’s winter doesn’t mean you can’t go on foot. Free Chicago Walking Tours offers two winter walking tours. One explores the Chicago Pedway, an underground system that crisscrosses beneath the city (and keeps walkers warm in the winter months). The second is a holiday tree & light tour where guests can get a guided tour of the Loop and River North neighborhoods decked out for the holidays.