What to do in Winnetka, IL

Activities, attractions and tours

Winnetka Attractions

Let Expedia help you to experience the best that Winnetka has to offer! If you’re planning a trip to Winnetka, 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 to Winnetka 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.

Places of interest in Winnetka

Winnetka is crammed with must-see places to visit and things to do. We can help you decide where to stay in Winnetka, and make it a breeze to explore Winnetka and 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 holiday 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 to Winnetka, 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 in Winnetka.

Winnetka attractions

Winnetka 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 in Winnetka to keep you entertained. Expedia makes it easy to book your flight, hotel and rental car in advance, making for hassle-free travel and freeing you up to explore the sights of Winnetka.

Looking for things to do in Winnetka 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 of Winnetka or catch up with the vibrant local culture, our guides to Winnetka attractions ensure that you’ll have a successful trip, whatever the season. Happy trails!

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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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Wrigley Field featuring a city, a sporting event and city views

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, shopping, restaurants and more can be found in this waterfront entertainment district.

3. 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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Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

4. 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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Millennium Park which includes autumn colours, modern architecture and street scenes

5. 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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Soldier Field which includes a high-rise building, a city and modern architecture

What to do in Winnetka

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Grant Park

Grant Park

4.5/5(96 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
Chicago Riverwalk featuring a river or creek, a bay or harbour and a city

Chicago Riverwalk

4.5/5(29 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk

 

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Day trip destinations from Winnetka

Chicago showing a city and a skyscraper as well as a family

Chicago