Holiday market & lights · Illinois

Chicago at the Holidays: Christkindlmarket to ZooLights day trip

Chicago at the Holidays: Christkindlmarket to ZooLights

A downtown Chicago holiday day that runs from morning into night: the Great Tree in Macy's Walnut Room, lunch and mulled wine at the Christkindlmarket in Daley Plaza, the city's tree and skating in Millennium Park, the Magnificent Mile's lit trees at dusk, and ZooLights at Lincoln Park Zoo as the finale.

Time: 10–11 hour day into evening
Driving: No car: 3–4 miles on foot downtown, then a CTA bus to the zoo and back
Best time: November 20 to December 23, Sunday to Thursday
Updated: October 14, 2026 at 11:32 PM Pacific

$4 USD

One-time purchase. You own your guide forever and can return for the latest update any time.

Wooden market stalls trimmed with garland and gingerbread hearts at night, under bare trees wrapped in white lights in front of a columned office tower — Daniel X. O'Neil · CC BY 2.0. November 2013 photograph of the Christkindlmarket at Daley Plaza; stall layout changes each year. Resized and displayed with crop.

Suggested times, not bookings

Your day at a glance

10:00 amMacy's on State Street and the Walnut Room
11:30 amChristkindlmarket at Daley Plaza
1:15 pmMillennium Park: the Chicago Christmas Tree and ice rink
2:00 pmMaggie Daley Park Ice Skating Ribbon
4:15 pmThe Magnificent Mile lights, and dinner
6:30 pmZooLights at Lincoln Park Zoo
8:30 pmBack downtown

Highlights

Worth the trip

The Great Tree in Macy's Walnut Room and the State Street windows
German food and Glühwein in a collectible mug at the Christkindlmarket
The Magnificent Mile at dusk, then ZooLights at Lincoln Park Zoo

What’s in the guide

Detailed stop guidance, rules, practical pitfalls, a route map, Google Maps, Waze and Apple Maps links and weather alternatives. Read it online any time, or keep it offline in the Greg’s Guides app for iPhone and iPad. See an example guide →

Plan for the conditions

Expected seasonal weather

From late November through December, downtown Chicago usually has highs in the 30s °F and nights in the 20s, colder with wind off Lake Michigan and on the river bridges. Snow and freezing drizzle are possible, and a cold snap can push wind chills below zero. The sun sets around 4:20 pm, so the second half of this day is in the dark. These are seasonal expectations, not a forecast for your travel date; check the NWS forecast the evening before and the morning of your trip.

Admission and parking are separate. Check current conditions before departure.

Another good day

More Midwest day trips

See every Midwest guide →

The wide Illinois River curving past a long wooded bluff in red, orange and gold fall color, with dark green pines at the water's edge and two small motorboats leaving wakes

Canyon hiking & state parks

Chicago → Starved Rock → French & Wildcat canyons → Starved Rock Lodge → St. Louis Canyon → Illinois Waterway Visitor Center → Matthiessen Dells → Utica

Starved Rock & Matthiessen

A canyon-hiking day trip from downtown Chicago to the Illinois River: the sandstone butte and overlooks at Starved Rock, French, Wildcat and St. Louis canyons, lunch at the 1930s Starved Rock Lodge, the lock and dam across the river, and the waterfalls of the Matthiessen Dells, timed around the weekend parking-lot closures.

11–12 hour day·About 4 hours of driving in total

Best: Late March to May, or mid-October

$4 USD

A wide, empty sand beach curving along Lake Michigan under a blue sky, with white-capped waves on the right and a wooded dune in orange and red fall color rising on the left

Dunes, beaches & lakeshore

Chicago → Indiana Dunes State Park → Visitor Center → Chesterton → Century of Progress Homes → West Beach

Indiana Dunes

A lakeshore day from downtown Chicago: the 3 Dune Challenge over the three tallest dunes in Indiana Dunes State Park, passes and maps at the Indiana Dunes Visitor Center, lunch in downtown Chesterton, the 1933 World's Fair houses on Lake Front Drive in Beverly Shores, and the Dune Succession Trail at West Beach, with the Chicago skyline across the water.

9–10 hour day·About 2 hours 30 minutes of driving in total

Best: September to mid-October

$4 USD

The long tile-roofed Riviera building and tour boats at their docks across a calm blue bay, with wooded shoreline and houses behind

Lake town, boat tour & shore walk

Chicago → Riviera Docks cruise → Downtown Lake Geneva → Geneva Lake Shore Path → Yerkes Observatory → Big Foot Beach State Park

Lake Geneva, Wisconsin

A summer day on Geneva Lake, about two hours from downtown Chicago: a morning boat tour from the Riviera Docks past the Gilded Age estates (on the U.S. Mailboat in season), lunch downtown, a walk on the public Shore Path from Library Park, a tour of Yerkes Observatory in Williams Bay and a late swim or walk at Big Foot Beach State Park.

11–12 hour day·About 4 hours of driving in all, most of it the round trip from Chicago

Best: Mid-June to mid-September

$4 USD

A footbridge with black iron railings crossing the grassy levee toward downtown Galena, where brick buildings and church steeples climb a wooded hillside under puffy white clouds

Historic small town & long road trip

Chicago → Horseshoe Mound → U.S. Grant Home → Grant Park → Main Street → Old Blacksmith Shop → Chicago

Galena

A long day from Chicago to Galena, the 1850s lead-mining river town in the far northwest corner of Illinois: a hilltop preserve with views into three states, a tour of the house Galena gave Ulysses S. Grant in 1865, a walk over the river to the brick storefronts of Main Street, and a working 1897 blacksmith shop.

12–13 hour day·About 3 hours each way via Interstate 90 and US 20; little driving once you are in Galena

Best: May to October; best on Friday to Sunday

$4 USD

Two red vintage gas pumps in front of the white clapboard Ambler's Texaco station in Dwight, with a green roof, shuttered window and flower box under a deep blue sky

Route 66 road trip

Begin Route 66 sign → Joliet → Gemini Giant → Polk-A-Dot Drive In → Ambler's Texaco → Odell Standard Oil → Pontiac

Illinois Route 66: Chicago to Pontiac

The first hundred miles of the Mother Road in its centennial year: a photo at the Begin Route 66 sign in downtown Chicago, Joliet's Route 66 Welcome Center and the 1926 Rialto, the Gemini Giant in Wilmington, burgers at Braidwood's Polk-A-Dot, two restored 1930s gas stations in Dwight and Odell, and the Route 66 Hall of Fame in Pontiac.

10–11 hour day·About 200 miles and 4½–5 hours of driving in all, out on old Route 66 and back on I-55

Best: May to October

$4 USD