What to do in Winnetka, IL

Activities, attractions and tours

Visit Winnetka

Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

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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Recommended things to do in Winnetka

Number of things to do	10
Cheapest thing to do on Expedia	Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago: £8
Top 5 things to do	Travel between Chicago O'Hare and Madison Rosemont: Two Flight Indoor Skydiving Experience Glow Workshop Neon Art Experience at Studio WIP Immersive Potsticker Cooking Class in Chicago BYOB Spray Paint and Sip at Studio W.I.P.
Half-day tours	Travel between Chicago O'Hare and Madison Rosemont: Two Flight Indoor Skydiving Experience Glow Workshop Neon Art Experience at Studio WIP Immersive Potsticker Cooking Class in Chicago BYOB Spray Paint and Sip at Studio W.I.P.
With kids	BYOB Spray Paint and Sip at Studio W.I.P.

What to do in Winnetka

Popular places to visit

Wrigley Field

4.5/5(40 reviews)

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

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.

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.

Navy Pier

4/5(125 reviews)

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

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.

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.

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.

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.

United Center

4.5/5(15 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

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

Chicago

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 kms (2 miles) 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.

BYOB Spray Paint and Sip at Studio W.I.P.

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.