What to do in Winnetka, IL

Activities, attractions and tours

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Winnetka Attractions

Let Expedia help you experience the best that Winnetka has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Activities and Tours

Winnetka is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Winnetka to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights.

Winnetka Attractions

Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Winnetka.

Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Winnetka attractions ensure that you’ll have a successful trip, whatever the season.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $44
per adult
96% of travellers recommend
Flyover in Chicago
LEGOLAND® Discovery Center Chicago

LEGOLAND® Discovery Center Chicago

CA $37
per adult
92% of travellers recommend
LEGOLAND® Discovery Center Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $48
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $71
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
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Top places to visit

1. Wrigley Field

Fans of baseball know Wrigley Field as the long-time home of the Chicago Cubs. Built in 1914, this is one of the oldest and best-known ballparks in the US. Some of the most memorable moments in baseball history have been played out here, including Babe Ruth’s now famous “called shot” in 1932 during the World Series. He allegedly pointed to the bleachers, predicting that he’d hit a home run, and then did. Legendary Cubs player Ernie Banks nicknamed the stadium "The Friendly Confines" because fans were wild about their team and ballpark. Catch a game and mingle with the passionate locals if you’re in town March through September.
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An aerial view of a baseball stadium surrounded by urban buildings.

2. Navy Pier

Navy Pier draws more than 8.6 million visitors each year. It has rides, restaurants, shops, parks and boat tours, all within a 50-acre pier on Lake Michigan. Open year-round, it’s busiest in the summer months when there are open-air stalls selling souvenirs and weekly firework displays.
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A Ferris wheel and a carousel at a fairground.

3. Soldier Field

Soldier Field has been one of Chicago’s most well-known landmarks since its construction in 1924 and is the oldest NFL stadium in the country.
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A large stadium surrounded by a cityscape with modern buildings.

4. Chicago Riverwalk

Get a sense of the culture and character of the Windy City by wandering along the Chicago Riverwalk. This scenic stretch of the city follows the banks of the Chicago River from near the edge of Lake Michigan through Downtown to where the river splits. As you follow the walkway, pass impressive bridges, fascinating museums and trendy dining spots.
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A river with boats, surrounded by tall buildings and a clear sky.

5. McCormick Place

McCormick Place is both the biggest convention center in Chicago and the biggest one anywhere in the U.S. This vast, sprawling complex is an impressive feat of architecture and engineering that was founded well over half a century ago. Attend an event here to get a sense of its incredible scale.
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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.

6. Millennium Park

Millennium Park is a 25-acre (10 hectare) park in the central Loop. Locals and tourists gather year-round for concerts, biking and jogging, and to admire the sculptures dotting the landscape. Conveniently located near other attractions, it’s easy to combine a walk through the park with a visit to the Art Institute of Chicago or shopping along the Magnificent Mile.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

What to do in Winnetka

Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Winnetka

A cityscape with tall buildings, a river, and a bridge at dusk.

Northbrook

A city skyline with modern skyscrapers and a river with boats and people in the foreground.

Chicago

An aerial view of a suburban area with a large parking lot, residential houses, and a mix of deciduous trees.

Northfield

Frequently asked questions

Is Winnetka worth visiting?
With a mix of golfing and nature, there's no shortage of things to do in Winnetka. While you're here, head to North Shore Beach Park, a major attraction in the area.
How do I spend a day in Winnetka?
Start your sightseeing with a visit to North Shore Beach Park and Loyola Beach. Then, explore other areas of Winnetka for local dining and some shopping.
What is the top tourist attraction in Winnetka?
Don't leave without visiting North Shore Beach Park, ranked the top tourist attraction in Winnetka.
Is three days enough to stay in Winnetka?
Three days will be plenty of time to tick off many city highlights, such as North Shore Centre for the Performing Arts, Clark Street Beach and Langdon Park Beach. The average stay in Winnetka is two days. If you have the urge to extend your adventure, Chicago isn't far away.
Is Winnetka a walkable city?
That depends on what you'd like to see and do in Winnetka. Several leading attractions, like Langdon Park Beach, are accessible on foot. If you're up for a wander through one of Winnetka's neighbourhoods, Gross Point is 3 kilometres away from the city centre.
What are some activities to do in Winnetka with kids?
If you're searching for activities and sights for all the family, we've got some fabulous ideas for what to do in Winnetka with kids.

What to do in Winnetka for adults?
FEW Spirits and Milwaukee Avenue are just a few of the things to do in Winnetka. With lots of activities available, there's something here for everyone to explore.
Are there free things to do in Winnetka?
From visiting parks to strolling around vibrant neighbourhoods, it's simple to find free things to do in Winnetka. If you need new ideas, ask for recommendations from a local tour guide. Clark Street Beach is a top spot for anyone planning to save on their sightseeing adventures.