Summary
Hosting family in Chicago for the holidays is easier with a plan built around who’s visiting. Grandparents and guests who prefer less walking can enjoy an architecture river tour, the Art Institute, Skydeck, and dinner with a view. Young kids will love Wintrust Winter WonderFest at Navy Pier, ZooLights, and the Shedd Aquarium, while teens and adults can try The Ledge, Christkindlmarket, and holiday shopping on the Magnificent Mile. The guide includes half-day, full-day, and weekend itineraries, ideas for Christmas Eve and Christmas Day, and hosting tips like booking before guests arrive, grouping plans by neighborhood, and pairing outdoor outings with indoor warm-up stops. Shoreline Sightseeing’s architecture river tours run through the end of 2026, with evening departures that show off the city’s holiday lights.
Table of Contents
- Things to Do in Chicago With Visiting Family: Quick Picks by Guest Type
- Where to Take Grandparents and Guests Who Prefer Less Walking
- Where to Take Families With Young Kids
- Where to Take Teens and Adults
- Holidays at Pioneer Court
- Sample Holiday Itineraries for Visiting Family
- What’s Open in Chicago on Christmas Eve and Christmas Day
- How to Entertain Guests Visiting for the Holidays
- Give Your Visitors a Chicago Holiday to Remember
- Frequently Asked Questions
When family comes to Chicago for the holidays, the easiest wins are downtown experiences that work for every age: an architecture river tour to see the city’s holiday lights from the water, Christkindlmarket, Wintrust Winter WonderFest at Navy Pier, a stroll down the decorated Magnificent Mile, and a warm-up at museums like the Shedd Aquarium or Museum of Science and Industry. Plan each day around one neighborhood, make reservations before guests arrive, and build in indoor breaks to keep everyone happy.
The holiday season is a time for family, friends, gratitude, and the joy of giving, and Chicago celebrates it in true style. But when relatives are staying with you, the question isn’t what’s happening in the city. It’s where to take the people in your guest room.
This guide from Shoreline Sightseeing covers the best things to do in Chicago with family visiting, broken down by who’s in town, how much time you have, and how to keep a mixed-age group comfortable. It covers the full holiday stretch, from Thanksgiving through Christmas, when there are plenty of things to do in Chicago during the holidays for every generation.
Things to Do in Chicago With Visiting Family: Quick Picks by Guest Type
| Who’s Visiting | Where to Take Them | Why It Works |
|---|---|---|
| Grandparents and guests who prefer less walking | Architecture river tour, Art Institute, Skydeck, dinner with a view | Big sights with plenty of time seated or indoors |
| Families with young kids | Winter WonderFest, ZooLights, Shedd Aquarium | Hands-on fun, warm indoor options, holiday magic |
| Teens and adults | The Ledge at Skydeck, Christkindlmarket, Magnificent Mile shopping, evening river tour | Thrills, shopping, food, and great photos |
| The whole group together | Architecture river tour, Christkindlmarket, holiday lights on Michigan Avenue | Something for every age in one outing |
Where to Take Grandparents and Guests Who Prefer Less Walking
For guests who’d rather not spend the day on their feet in the cold, focus on experiences where the sights come to you.
- A river tour. An architecture river tour shows off dozens of landmarks while guests stay seated. On chilly days, the lower deck is enclosed by weather flaps for extra protection. Seating isn’t heated, so bundle up.
- The Art Institute of Chicago. Renowned collections, with benches throughout and a cafe for breaks.
- Skydeck Chicago. Sweeping views of the city from Willis Tower, no hiking required.
- A holiday dinner out. Browse options for dining with a view in Chicago and book early for holiday weekends.
Traveling with guests who have mobility needs? Review Shoreline’s accessibility information before booking, and check accessibility details for other attractions ahead of time.
Where to Take Families With Young Kids
Young visitors need a mix of excitement and warm-up breaks. These picks deliver both.
- Wintrust Winter WonderFest at Navy Pier. Indoor rides, a holiday forest, and ice skating under one roof, open from November 27, 2026, into early January 2027.
- ZooLights at Lincoln Park Zoo. A glowing evening outing that’s easy to fit in after an early dinner.
- The Shedd Aquarium. A reliable favorite when the weather turns.
For more ideas, including skating rinks and sledding spots, explore these family-friendly winter activities in Chicago.
Where to Take Teens and Adults
Older guests often want something they can’t do at home. Try these:
- The Ledge at Skydeck Chicago. A glass balcony that extends 4.3 feet out from Willis Tower, far above the city.
- Christkindlmarket. German food, spiced mulled wine for the adults, and one-of-a-kind gifts.
- Holiday shopping on the Magnificent Mile. Decorated storefronts and holiday lights along North Michigan Avenue.
- An evening river tour. Evening departures show off the Chicago buildings that transform for the holidays.
Holidays at Pioneer Court
Right next to the Michigan Avenue Dock, Pioneer Court is the largest privately owned plaza in Chicago and has hosted a European-style holiday market in past seasons. Check this season’s schedule before you go, and explore more things to do near Michigan Avenue while you’re in the area.
Sample Holiday Itineraries for Visiting Family
Half Day: The Michigan Avenue and River Loop
| When | Plan |
|---|---|
| Afternoon | Walk the Riverwalk and see the Wrigley Building and Tribune Tower at the Michigan Avenue bridge. |
| Late afternoon | Take an architecture river tour as the holiday lights come on. |
| Evening | Stroll the decorated Magnificent Mile and finish with dinner nearby. |
Full Day: Downtown Holiday Highlights
| When | Plan |
|---|---|
| Morning | Skate at Millennium Park or the Maggie Daley Park Skating Ribbon (reservations required), or visit the Art Institute. |
| Lunch | Graze at Christkindlmarket downtown (check this season’s location and hours). |
| Afternoon | Take an architecture river tour, timed for late afternoon to catch the holiday lights. |
| Evening | Dinner with a view, then a walk past the lights on Michigan Avenue. |
Holiday Weekend: Something for Everyone
| Day | Plan |
|---|---|
| Saturday | Spend the morning at Winter WonderFest at Navy Pier, head to Michigan Avenue for holiday shopping, then catch an evening river tour. |
| Sunday | Explore the Shedd Aquarium or Museum of Science and Industry in the morning, then see ZooLights in the evening. |
Hosting over Thanksgiving? Build around the parade and a boat tour before dinner with these things to do in Chicago over Thanksgiving weekend. Arriving the weekend before? Don’t miss the Magnificent Mile Lights Festival.
What’s Open in Chicago on Christmas Eve and Christmas Day
If your guests are in town for Christmas itself, plan ahead. Many museums, attractions, and restaurants close or shorten hours on Christmas Eve and Christmas Day, and holiday events often have special schedules. A few ideas that tend to work well:
- Ice skating. The Maggie Daley Park Skating Ribbon’s 2026-27 schedule includes Christmas Eve and Christmas Day sessions from 8 a.m. to 4 p.m. Reservations are required.
- A holiday lights walk. Michigan Avenue, the Riverwalk, and the decorated buildings along the river make for a festive evening stroll that doesn’t depend on opening hours.
- Christmas Eve outings. Many seasonal events run on Christmas Eve with shortened hours, so check schedules and plan earlier in the day.
Always confirm holiday hours before heading out, since schedules can change year to year.
How to Entertain Guests Visiting for the Holidays
- Book before they arrive. River tours, skating sessions, and holiday dinners fill up on weekends, so reserve the must-dos ahead of time.
- Stick to one area per day. Grouping plans around Michigan Avenue, the Loop, or Navy Pier cuts down on travel and keeps everyone fresh.
- Plan warm-up stops. Pair every outdoor activity with an indoor break, like a museum, a cafe, or Winter WonderFest.
- Have a bad-weather backup. Keep an indoor option in your back pocket in case of snow or wind.
- Skip the car when you can. Downtown parking is expensive during the holidays. The CTA and, when available, the water taxi make getting around easier.
- Pace it for the group. Mixed-age groups do best with one or two big outings a day and downtime in between.
- Mix in free outings. Keep the budget in check with some of these family-friendly winter activities in Chicago, several of which are free.
- Check holiday hours. Many attractions change hours on Thanksgiving, Christmas Eve, and Christmas Day.
Give Your Visitors a Chicago Holiday to Remember
Whether your guests are here for Thanksgiving, a December weekend, or Christmas week, Chicago has a way to make every generation feel the holiday spirit. Add a river tour with Shoreline Sightseeing to see the city’s lights from the water, and you’ll give your visitors a view of Chicago they’ll be talking about long after they head home.
Frequently Asked Questions
Popular picks include an architecture river tour, Christkindlmarket, Wintrust Winter WonderFest at Navy Pier, ZooLights at Lincoln Park Zoo, the decorated Magnificent Mile, and museums like the Shedd Aquarium and Art Institute of Chicago. Choose based on your guests’ ages and how much walking they’re comfortable with.
December visitors can enjoy holiday markets, light displays, ice skating, indoor festivals, museums, observation decks, and evening river tours that show off the city’s holiday lights.
Plan one or two big outings a day, group activities by neighborhood, book popular experiences in advance, and pair outdoor fun with indoor warm-up stops. Having a bad-weather backup keeps plans flexible.
Good options for grandparents include an architecture river tour, the Art Institute of Chicago, Skydeck Chicago, and dinner with a view. These experiences offer big sights with plenty of time seated or indoors.
A full day downtown might start with skating or a museum, continue with lunch at Christkindlmarket, and end with a late-afternoon architecture river tour and dinner. For a weekend, add a day at Navy Pier’s Winter WonderFest and an evening at ZooLights.
Many museums, attractions, and restaurants close or shorten hours on Christmas Day, so check schedules in advance. The Maggie Daley Park Skating Ribbon’s 2026-27 schedule includes Christmas Day sessions from 8 a.m. to 4 p.m., and a walk to see the holiday lights on Michigan Avenue and along the river works any time.
Free options include browsing Christkindlmarket, walking the decorated Magnificent Mile, strolling the Riverwalk to see the holiday lights, and sledding the hill by Soldier Field when conditions allow.
Yes. Shoreline Sightseeing’s architecture river tours run through the end of 2026. Check the current schedule for dates and departure times.
Downtown is easy to explore on foot and by CTA train or bus. Grouping each day’s plans around one area, like Michigan Avenue, the Loop, or Navy Pier, cuts down on travel.
