Where to Take Visiting Family in Chicago for the Holidays

Where Should You Take Out-of-Town Family in Chicago for the Holidays?

Top picks for out-of-town family include Holidays @ Skydeck, Christkindlmarket, the Millennium Park Christmas tree, and a holiday show, matched to who’s visiting. Start with one indoor anchor everyone can enjoy, then add an outdoor tradition or two when the weather cooperates. Here’s how to match your guests to the best things to do in Chicago this holiday season.

Who’s visiting	Best fit	Why it works
Grandparents and older relatives	Holidays @ Skydeck, Macy’s on State Street, A Christmas Carol at the Goodman	Warm, indoor, and easy on the feet
Families with young kids	Holidays @ Skydeck, ZooLights at Lincoln Park Zoo, Winter WonderFest at Navy Pier	Santa, twinkling lights, and hands-on fun
Teens and adult siblings	The Ledge at Skydeck, the Maggie Daley Park Skating Ribbon, Christkindlmarket	Photo-worthy moments and a little thrill
First-time visitors	Skydeck, Millennium Park and the city’s Christmas tree, Christkindlmarket	The iconic sights, dressed for the season
Relatives who’ve seen it all	Holidays @ Skydeck at sunset, Lightscape at Chicago Botanic Garden, the Joffrey Ballet’s The Nutcracker	A new way to see a city they already know

Why Is Holidays @ Skydeck a Great Place to Take Visiting Family?

Holidays @ Skydeck is a strong choice for visiting family because it works for every age and every kind of weather. From November 13, 2026, through January 4, 2027, Skydeck at Willis Tower, in the Loop at 233 S. Wacker Drive, decorates its Chicago Museum and 103rd-floor observation deck with thousands of twinkling lights, holiday décor, and Santa photo ops. Every Skydeck ticket includes a 3-in-1 experience: the views, the interactive Chicago Museum, and The Ledge, glass balconies that extend 4.3 feet out from the 103rd floor, 1,353 feet above the street.

For a local host, that makes Holidays @ Skydeck one of the simplest Chicago holiday plans for a mixed-age group. Kids get Santa and the lights, older relatives get a warm indoor visit, and the cousins who think they’ve “done Chicago” get a view of the city they haven’t seen before, all inside one downtown address.

What Will Your Family See at Holidays @ Skydeck?

A Holidays @ Skydeck visit includes the full Skydeck experience, with seasonal touches from the museum to the top floor:

• Holiday lights and décor: Thousands of twinkling lights and festive décor fill the Chicago Museum and the observation deck.
• Santa photo ops: Themed holiday backdrops, photo opportunities with Santa, and informal Selfies with Santa.
• Seasonal live performances: Live holiday entertainment adds to the atmosphere during the season.
• The Ledge: The Ledge lets your family step out onto glass, 1,353 feet above the city, for a holiday photo with the whole skyline below.
• The views: On a clear day, the view from America’s highest observation deck stretches up to 50 miles and across four states.

How Does Holidays @ Skydeck Work for Every Age?

Holidays @ Skydeck gives each generation something different to enjoy during the same visit:

Who’s visiting	What they’ll love	Good to know
Young kids	Santa photo ops, the holiday lights, and standing on The Ledge	Share a few Willis Tower fun facts on the way up
Teens	Ledge photos and the skyline after dark	Find your Ledge photos after the visit
Adults	Sunset views and a dinner above the city	Upgrades like Pie in the Sky require reservations
Grandparents and older relatives	Views from America’s highest observation deck without standing out in the cold	The Ledge is wheelchair accessible, and Skydeck is KultureCity certified sensory inclusive
Large family groups	One plan that keeps everyone together	Group visit options make planning easier

Which Holiday Extras Are Worth Booking?

If your family is in town to celebrate, a Skydeck upgrade turns the visit into an occasion:

• Pie in the Sky: A three-course Giordano’s Chicago-style pizza dinner on the 99th or 103rd floor, offered on select evenings with a maximum of seven tables per night. During past holiday seasons, Holiday Pie in the Sky added a seasonal dessert and Christmas music.
• The Ultimate Sunset Experience: Reserved west-facing seating on the 99th floor, champagne or sparkling cider, dessert, and expedited access to The Ledge.
• Golden Hour Drink Package with Kindling: Sunset views and priority Ledge access, followed by an espresso martini at Kindling, for the adults in the group.
• Skydeck and Color Factory bundle: Pair your visit with Color Factory’s interactive art exhibits, just steps away inside Willis Tower.

What Should You Know Before Visiting Skydeck With Family?

• Time your visit for sunset. December sunsets come early, so an afternoon visit lets your family watch the skyline shift from daylight to holiday lights.
• Book tickets ahead. The holiday season is a popular time to visit, and booking ahead keeps the day on schedule. Holiday hours can vary, so check hours before you go.
• Skip the drive. Willis Tower is a few minutes’ walk from the Quincy ‘L’ station (Brown, Orange, Pink, and Purple lines) and from Union Station’s Metra trains, so relatives coming in from the suburbs can leave the car at home.
• Plan parking. If you’re driving in with relatives, reserve discount parking before you leave home.
• Eat at Catalog. Catalog at Willis Tower puts dining like Tortazo by Rick Bayless and Kindling by Jonathon Sawyer steps from Skydeck. Holiday hours vary by restaurant.

Where Should You Take Grandparents and Older Relatives?

With grandparents and older relatives, choose warm, mostly indoor stops with short distances between them. These picks keep the day festive without long stretches in the cold:

• Holidays @ Skydeck: Holiday décor, Santa, and views from America’s highest observation deck, all indoors at Willis Tower.
• Macy’s on State Street: The holiday window displays have long been a Chicago tradition, and the Walnut Room’s Christmas tree has been a classic stop inside for generations.
• A Christmas Carol at the Goodman Theatre: The Goodman’s 49th annual production of the Dickens classic is a seated, all-ages holiday tradition in the Loop.
• Christmas Around the World at Griffin Museum of Science and Industry: The museum’s annual exhibit features trees decorated in holiday traditions from cultures around the globe. Griffin MSI is one of several Chicago museums that make an easy warm-up stop with older guests.

Where Should You Take Visiting Family With Young Kids?

With young kids, plan around lights, Santa, and places where little ones can move around. These stops tend to be the biggest hits:

• Holidays @ Skydeck: Santa photo ops, twinkling lights, and the thrill of standing on The Ledge.
• ZooLights at Lincoln Park Zoo: Lincoln Park ZooLights fills the zoo with holiday lights in the evenings, and kids can walk off energy between displays.
• Wintrust Winter WonderFest at Navy Pier: Winter WonderFest is Navy Pier’s indoor holiday celebration, with an ice-skating rink and the Arctic Express Train, and the rest of Navy Pier is an easy add-on.
• Christmas Around the World: Kids love walking through the forest of decorated trees at Griffin MSI.

Once the decorations come down, the city still has plenty of things to do in Chicago with kids.

Where Should You Take Teens and Adult Siblings?

Teens and adult siblings usually want something a little more active, photogenic, or unexpected. Try these:

• The Ledge at Skydeck: Standing on glass 103 floors up is the kind of photo that ends up on everyone’s feed.
• Ice skating downtown: The Maggie Daley Park Skating Ribbon and the McCormick Tribune Ice Rink in Millennium Park offer skyline views once they open for the season. Check dates and reservation requirements before you go.
• Christkindlmarket: Browse ornaments and German-style food and drinks at Christkindlmarket in Daley Plaza or at Gallagher Way in Wrigleyville.
• Golden Hour with Kindling: For adult siblings, a sunset drink package at Skydeck makes an easy start to a night out.

What If Your Family Has Already Seen the Big Sights?

When your relatives have visited before, look for seasonal twists on familiar places and a few experiences outside the usual loop:

• Holidays @ Skydeck at sunset: Even if they’ve been to Skydeck, a holiday visit at dusk feels completely different, with seasonal décor inside and the city lighting up below.
• Lightscape at Chicago Botanic Garden: Lightscape is an illuminated 1.3-mile trail in Glencoe that’s curated anew each year, so it’s worth the drive even for repeat visitors. Book early, since popular dates go fast.
• The Joffrey Ballet’s The Nutcracker: Christopher Wheeldon’s Chicago version sets the story in 1892, as the city prepares for the World’s Columbian Exposition, at the Lyric Opera House.
• Holiday lights downtown: The best spots to see Christmas lights in downtown Chicago are easy to string together into an evening walk.

What’s an Easy One-Day Holiday Plan With Visiting Family?

An easy one-day plan starts at Millennium Park and works west through the Loop to Willis Tower, ending at Skydeck around sunset. The stops sit close together, so your group can walk between them and warm up indoors along the way.

• Morning: Millennium Park. Start with photos at the city’s Christmas tree and Cloud Gate, and add a skate at the McCormick Tribune Ice Rink if it’s open for the season.
• Late morning: Macy’s on State Street. Walk west to see the holiday windows, then head inside to warm up.
• Lunch: Christkindlmarket at Daley Plaza. Graze the German-style food stalls and browse ornaments a block west of Macy’s.
• Afternoon: Holidays @ Skydeck. Willis Tower is a short walk from Daley Plaza. Arrive in the mid-to-late afternoon to see the holiday décor, step out on The Ledge, and catch sunset from the 103rd floor.
• Evening: Dinner at Willis Tower. Stay for dinner at Catalog, or reserve Pie in the Sky for a pizza dinner above the city on select evenings.

If walking between stops is too much for some of your guests, a short rideshare covers the gaps.

What Are Free Things to Do With Visiting Family in Chicago?

Several of Chicago’s best-known holiday traditions are free, which helps when you’re hosting a full house:

• Christkindlmarket at Daley Plaza: The market is free to enter, so you only pay for the food, drinks, and gifts you choose.
• The city’s Christmas tree: The official City of Chicago Christmas tree in Millennium Park is free to visit, and Cloud Gate is a few steps away.
• Macy’s holiday windows: The State Street window displays are free to enjoy from the sidewalk.
• The Magnificent Mile lights: An evening walk along Michigan Avenue to see the holiday lights costs nothing.

When it’s time for a ticketed stop, there are several ways to save on Skydeck tickets, including CityPASS.

What Is Open in Chicago on Christmas Eve and Christmas Day?

Skydeck is open 365 days a year, including Christmas Eve and Christmas Day, so it’s an easy plan when family is in town for the holiday itself. Many museums, restaurants, and attractions close or shorten their hours on December 24 and 25, so confirm each stop before you go. Christkindlmarket at Daley Plaza runs through Christmas Eve, and the Wrigleyville market stays open through December 31.

Which Chicago Holiday Events Should Your Family Plan Around?

A few of the season’s biggest moments are worth building a visit around:

• Thanksgiving week: Relatives in town for Thanksgiving can start the holiday at the Chicago Thanksgiving Parade on State Street, then fill the long weekend with Christkindlmarket and Winter WonderFest. Several of the city’s largest museums close on Thanksgiving Day, so check what’s open in Chicago on Thanksgiving before you set the schedule.
• December: If your guests have never visited Chicago in December, give them a heads-up: daytime highs typically sit in the mid-30s, and wind off the lake makes it feel colder.
• New Year’s Eve: Family staying through the end of the month can ring in the new year with Navy Pier’s midnight fireworks and other New Year’s Eve events in Chicago.

Plan Your Family’s Holiday Visit to Skydeck

Whoever is coming to town this season, Holidays @ Skydeck gives the whole group a shared moment 103 floors above Chicago, with holiday lights, The Ledge, and the Chicago Museum all in one visit. Book ahead so your visit fits around the rest of your holiday plans.

Visiting Family in Chicago for the Holidays: FAQs

Where should I take out-of-town guests in Chicago during the holidays?

Holidays @ Skydeck at Willis Tower is a strong all-ages pick, with holiday décor, Santa photo ops, and views from the 103rd floor. Pair it with Christkindlmarket, the Christmas tree in Millennium Park, or the holiday windows at Macy’s on State Street for a full day downtown.

What is a good holiday activity in Chicago for all ages?

Holidays @ Skydeck works for every generation in a single visit, with Santa photo ops, holiday décor, The Ledge, and the Chicago Museum under one roof. It runs November 13, 2026, through January 4, 2027.

Is Skydeck accessible for older relatives?

Yes. The Ledge is wheelchair accessible, and Skydeck is KultureCity certified sensory inclusive. The full experience is indoors, so older relatives can enjoy the views without time out in the cold.

What can you do in Chicago with family when it’s too cold to be outside?

Indoor holiday options include Holidays @ Skydeck at Willis Tower, Winter WonderFest at Navy Pier, Christmas Around the World at Griffin Museum of Science and Industry, and holiday shows like A Christmas Carol at the Goodman and the Joffrey Ballet’s The Nutcracker.