A Christmas weekend in Chicago, a 2-day itinerary

Sample itinerary. This plan shows the format and level of detail of a VanSledright Travel itinerary. Opening hours, prices, season dates and booking rules change every year, so confirm the details with each provider before you book. Each day ends with a breakfast, lunch and dinner pick near that day’s stops; price levels run from $ (inexpensive) to $$$$ (a splurge), and restaurants change too, so check before you go.

This plan is built for the holiday season only. For a first visit at any other time of year, with the museums, the river cruise and the neighborhoods, see our 3 days in Chicago itinerary. To add the region’s other German and Dutch markets, our Midwest Christmas markets road trip spends two of its 11 days in Chicago.

Where should you stay for a Christmas weekend in Chicago?

Stay in the Loop. The city tree, the ice rink, Macy’s on State Street, Christkindlmarket and both theaters in this plan are within about a ten-minute walk of each other, which matters when it is cold. A hotel near State Street or Michigan Avenue between Randolph and Monroe puts you in the middle of all of it.

River North and the Magnificent Mile also work, and put you closer to the Michigan Avenue lights on day 2. Hotel prices rise on December weekends, so book early.

How do you get around Chicago in winter?

Walk the short hops and use the CTA for the rest. You can pay on ‘L’ trains and buses with a contactless bank card or phone, or with a Ventra card. From O’Hare, the Blue Line runs to downtown around the clock. From Midway, take the Orange Line to the Loop.

You don’t need a car. Parking downtown is expensive, and everything on day 1 is on foot. For the trip to Lincoln Park on day 2, take a CTA bus or a rideshare. From late November to late December the CTA also runs a decorated Holiday Train on its regular routes at normal fares; the schedule is posted each season on the CTA website.

Day 1: The tree, the ice rink, the Walnut Room and Christkindlmarket

Morning. Start in Millennium Park. The city’s Christmas tree stands near Michigan Avenue and Washington Street. In 2026 it is lit from November 20 to January 10, 2027. Skate at the McCormick Tribune Ice Rink below the Bean: admission is free, but you need to reserve a time slot online, and skate rental costs extra. When you get cold, cross Michigan Avenue to the Chicago Cultural Center, which is free to enter and has a Tiffany glass dome in Preston Bradley Hall.

Afternoon. Walk two blocks west to Macy’s on State Street, the former Marshall Field’s. The store has decorated its State Street windows for the holidays for decades; check that they are up before you go. Take the elevator to the seventh floor for lunch in the Walnut Room, where the Great Tree stands in the middle of the dining room. Only guests with a reservation can go in. After lunch, walk a block west to Christkindlmarket in Daley Plaza, a German-style outdoor market with wooden stalls selling ornaments, bratwurst and hot mulled wine. It is free to enter, and quieter on weekdays.

Day 1 evening: a holiday show

Evening. See a holiday show. The Goodman Theatre has staged A Christmas Carol every year for about five decades; in 2026 it runs November 13 to December 31. The Joffrey Ballet’s The Nutcracker, set in Chicago on the eve of the 1893 World’s Fair, plays at the Lyric Opera House from December 4 to 27, 2026. Both theaters are in the Loop. Have an early dinner first, then walk back past the tree on your way to the hotel.

Where to eat on day 1

• Breakfast: Goddess and the Baker (the Loop, $$). A cafe and bakery at 33 South Wabash Avenue, a block west of Millennium Park, for coffee and breakfast before you go out in the cold.
• Lunch: The Walnut Room (Macy’s on State Street, $$$). Lunch beside the Great Tree on the seventh floor, a Chicago holiday tradition. Reservation only during the holidays, with tables limited to 90 minutes; book as soon as dates open.
• Dinner: Italian Village (the Loop, $$$). Family owned since 1927, on Monroe Street, a short walk from the Goodman Theatre and the Lyric Opera House. Tell them your curtain time when you book.

Day 2: The Art Institute, Michigan Avenue and ZooLights

Morning. The Art Institute of Chicago opens at 11am, so have a slow breakfast first. Give the museum two to three hours: the Impressionist galleries, Hopper’s Nighthawks and Wood’s American Gothic are the usual first stops. The museum is closed on Tuesdays. If you are traveling with children, or you have already seen the Art Institute, go instead to the Griffin Museum of Science and Industry in Hyde Park for Christmas Around the World and Holidays of Light, a display of more than 50 decorated trees that has run since 1942. It opens on November 7 in 2026.

Afternoon. After lunch, head north on Michigan Avenue and cross the river. In recent years the Wrigley Building has put a decorated tree under its archway, on the left just past the bridge. North of the river the avenue becomes the Magnificent Mile, where more than 200 trees are wrapped in lights for the season; they are switched on at the Magnificent Mile Lights Festival, a parade and fireworks held on November 21 in 2026. It gets dark early in December, and the lights look best from about 4:30pm.

Day 2 evening: ZooLights

Evening. Take a CTA bus or a rideshare a couple of miles north to Lincoln Park Zoo for ZooLights, when the zoo grounds are covered in light displays. In 2026 it runs from November 20 to January 3, 2027, from 4:30pm to 9pm, with last entry at 8pm. The zoo is free during the day, but ZooLights needs a ticket for everyone, including infants. As of 2026, tickets for a fixed date cost $7 to $12 in advance and $20 on the day, and most Mondays are free with a ticket reserved a week ahead. Allow an hour and a half, and eat across the street before or after.

Where to eat on day 2

• Breakfast: Lou Mitchell’s (West Loop, $$). A diner open since 1923 on Jackson Boulevard, known for handing out donut holes while you wait. A good long breakfast before the museum opens at 11am. Closed Monday and Tuesday.
• Lunch: Miller’s Pub (the Loop, $$). A wood-paneled Loop restaurant open since 1935 on Wabash Avenue, a block and a half from the Art Institute, with the kitchen open from 11am every day.
• Dinner: R.J. Grunts (Lincoln Park, $$). Burgers and hand-spun shakes in a 1970s room, open since 1971 and steps from the zoo. It closes at 8:30pm from Sunday to Wednesday, so on those nights eat before ZooLights.

When is the best time for a Christmas trip to Chicago?

Go between the Friday before Thanksgiving week and December 23. Christkindlmarket in Daley Plaza typically runs from mid-November to Christmas Eve; in 2026 the dates are November 20 to December 24. The city tree is lit the same evening the market opens in 2026, November 20, and the ice rink opens that day too.

The first two weeks of December are the easiest: everything is open and The Nutcracker has started. Weekdays are quieter than weekends at the market and at ZooLights. If you arrive on a Friday in December, the city holds a holiday sing-along in Millennium Park at 6pm on December 4, 11 and 18 in 2026.

Avoid planning around Thanksgiving Day, Christmas Eve or Christmas Day themselves. The market closes early on Thanksgiving and at 4pm on its last day, and museums and restaurants keep holiday hours. Dates for every event here are set year by year, so check the official pages in the sources below for the year you travel.

What should you book ahead for Christmas in Chicago?

Book these before you arrive, especially for a December weekend:

• Your holiday show, A Christmas Carol or The Nutcracker. Weekend performances sell out first.
• The Walnut Room. It is reservation only during the holidays, and tables near the tree can’t be guaranteed.
• An ice rink time slot in Millennium Park. It is free but must be reserved online.
• ZooLights tickets for a fixed date, which cost less than buying on the day.
• Timed museum tickets for the Art Institute or the Griffin Museum of Science and Industry.
• Your hotel. Loop hotels fill on December weekends.

Want a Chicago holiday plan built for your trip?

This sample is written for two adults on a Saturday and Sunday in December. A custom plan starts from your own dates, budget, pace and interests: a trip with young children, a third day for the museums, a different show, or a New Year’s visit.

A custom itinerary for a trip of up to 3 days is $79. Send your details through the form below and we’ll confirm the plan and the price by email before you pay anything. See pricing for longer trips.