Chicago Christmas Markets: A Day Trip From Wisconsin
Christkindlmarket, the Mag Mile Lights and ZooLights in One Day, Without Driving, Parking or a Late-Night Drive Home
By the Milwaukee to O’Hare Team · Updated October 2026
Milwaukee to O’Hare, the airport-route division of Pharaoh’s Transportation — 5151 S Howell Ave, Milwaukee, WI 53207. Flat-rate car service between Wisconsin and O’Hare, Midway and downtown Chicago, both ways. Available 24/7. (414) 322-3751 · info@milwaukeetoohare.com· book online.
Quick answer: A day trip from Wisconsin to Chicago’s Christmas markets and holiday lights is easiest with a private chauffeur. Chicago’s Christkindlmarket opens Friday, November 20, 2026, at Daley Plaza and Wrigleyville, the Magnificent Mile Lights Festival is Saturday, November 21, and ZooLights runs November 20 through January 3. With a chauffeur, you skip downtown parking, move between stops on your schedule and ride home to Wisconsin relaxed instead of driving late at night.
What’s On This Season
Christkindlmarket at Daley Plaza. Chicago’s German-style holiday market opens November 20 and runs through December 24 in the Loop. It’s free to visit, and organizers suggest bringing cash, since many vendors don’t take cards. NBC Chicago has the full 2026 schedule.
Christkindlmarket Wrigleyville. A second location next to Wrigley Field opens the same day and stays open through December 31. On weekdays, it opens in the afternoon, so plan an evening visit.
Magnificent Mile Lights Festival. Held Saturday, November 21, the festival lights up Michigan Avenue, and the lights stay on through the winter for an evening stroll.
ZooLights at Lincoln Park Zoo. Running November 20 through January 3, ZooLights fills the zoo with holiday lights after dark.
A Sample Day From Wisconsin
Late morning: Your chauffeur picks you up at home in Milwaukee, Madison or anywhere in between.
Afternoon: Browse the market at Daley Plaza, grab a warm drink and shop for gifts.
Early evening: Dinner downtown, then a walk down the lit-up Magnificent Mile.
Evening: Finish at ZooLights or the Wrigleyville market before heading home.
Night: Ride back to Wisconsin while someone else handles the drive.
Why Not Just Drive?
Downtown Chicago parking is expensive and scarce during the holidays, and moving the car between the Loop, Michigan Avenue and Lincoln Park eats into your day. Then there’s the drive back to Wisconsin in the dark, often in winter weather, after a long day on your feet. A chauffeur turns all of that into a single, easy ride.
The Real Difference Is the Ride Home
Getting to Chicago is easy. Getting home late, tired and full of holiday food is the hard part. With a private chauffeur, the end of the night is the most relaxing part of the trip instead of the most stressful.
How It Works
Book a round trip with hourly service, and your chauffeur and vehicle stay with you for the full booked time. Our guide to round trips between Wisconsin and Chicago explains the options, and our Chicago routes page lists pickups from Milwaukee, Madison and Lake Geneva. For trips from farther away, see our long-distance limo service.
Choosing Your Vehicle
Sedan, up to 3. A couple’s holiday date.
SUV, up to 6. A family with room for shopping bags.
Sprinter, up to 14. Friend groups, office outings and extended family.
See every vehicle on our fleet page.
Tips for the Day
Dress warmly, since the markets and light displays are outdoors. Bring cash for market vendors. Go on a weekday afternoon if you want smaller crowds, and book early, because weekends between Thanksgiving and Christmas fill up fast. Our reviews page shows what other Wisconsin travelers say about riding with us.
Frequently Asked Questions
When does Chicago’s Christkindlmarket open in 2026?
The Daley Plaza and Wrigleyville markets both open Friday, November 20, 2026. Daley Plaza runs through December 24, and Wrigleyville runs through December 31.
When is the Magnificent Mile Lights Festival?
Saturday, November 21, 2026, the Saturday before Thanksgiving. The lights stay up on Michigan Avenue through the winter.
When is ZooLights at Lincoln Park Zoo?
ZooLights runs from November 20, 2026, to January 3, 2027.
Can our chauffeur wait while we explore?
Yes. With hourly service, your chauffeur and vehicle stay with you for the full booked time, so you can move between the market, dinner and the lights without rebooking or parking.
Which vehicle works for a holiday group?
A sedan seats up to 3, an SUV up to 6 and a Sprinter up to 14, so families and friend groups can ride together.
How much does a holiday day trip cost?
It depends on your pickup location, vehicle and number of hours. Call (414) 322-3751 for a custom quote.
How do I book?
Book online or call (414) 322-3751. We’re available 24/7.
Find Out Which Ride Fits Your Holiday Trip
Whether you need a sedan for two or a Sprinter for the whole family depends on your group and your plans, not on who has to drive home. Book your holiday day trip online or call (414) 322-3751. Still have questions? Check our FAQ or reach out directly.
Milwaukee to O’Hare · 5151 S Howell Ave, Milwaukee, WI 53207 · (414) 322-3751 · info@milwaukeetoohare.com · Open 24/7
