What to do in Winnetka, IL

Activities, attractions and tours

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.

Places to Visit in Winnetka

Ready for the adventure of a lifetime? Let Expedia.co.nz help you find the most exciting and fun things to do in Winnetka, Chicago while also allowing you to save a ton on travel arrangements. Regardless of whether you’re an urban explorer or an intrepid outdoor enthusiast, we can help you decide exactly what to do and see during your time in town.

Our thorough travel guides offer you an insider’s perspective on all of the best Winnetka attractions from NZ$18, making it easy for you to decide which places to visit and when. And by using Expedia.co.nz to set your sightseeing schedule, you can take in more of the enchanting attractions this area is famous for.

From group Winnetka tours and must-see landmarks to personal guides who take you off-the-beaten track, Expedia.co.nz offers you over 10 of the most popular events, activities, and attractions in this corner of the world. So whether you’re travelling alone, alongside a loved one, or with the whole family in tow, be sure to browse through our extensive travel guides prior to your plane touching down in this spectacular Winnetka. We even have a massive selection of flights, car hires, and accommodation for you to choose from. So what are you waiting for? Start your search today, and you’ll be having the time of your life before you know it.

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Top places to visit

1. Wrigley Field

For sports-fans, Chicago is about one of two things – the Bears or the Cubs. But while the Chicago Bears football team switched from Wrigley Park in 1971, its legendary baseball team, the Chicago Cubs, have stuck true to their long heritage here. They've stayed put at one of America's most iconic sports fields, ever since it was built in 1914. After all, Wrigley Park has legendary sporting triumphs (and disasters) steeped into every seat, and written on every leaf of its ivy-covered outfield walls.
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Wrigley Field showing a city and landscape views

2. 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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McCormick Place showing a high rise building and a city

3. Navy Pier

Navy Pier has been many things to Chicago, since it first struck out its 1006 metres into Lake Michigan in 1916. It was once a transport hub, a navy training centre, and even a place for the city to cool down in the days before air-conditioning. Now it’s the capital of fun for Chicagoans, home to circuses, fun fairs, fireworks and flower shows. It's one of the city's most popular attractions when summer arrives, and its twice-weekly firework shows begin. It's also a great launching off point for getting all nautical along Lake Michigan's 483-kilometre length.
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Navy Pier featuring a sunset and rides

4. Millennium Park

You may know Chicago as the Windy City. But its motto is actually Urbs in Horto - or 'City in a Garden.' And parks, large and small, abound in this surprisingly spacious city on Lake Michigan's shore. But none is quite like the Millennium Park, which was added to Chicago's long park list just this side of the new millennium (2004 to be exact – punctuality isn't big with Chicagoans). Less a park, more a 'new kind of town square', Millennium Park is a very 21st-century blend of art, open-spaces, dramatic vistas and engrossing events.
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Reflection of a Chicago buildings in a mirror of Chicago Bean, Millennium Park, Chicago city, USA., Shutterstock ID 1129809965, Purchase Order: SP-2109, Order Number: SP-2109 Qantas AU US Sale New Ads

5. 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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Chicago Riverwalk showing a city, a river or creek and a ferry

What to do in Winnetka

Discover the most popular places to visit in Winnetka

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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 showing a high rise building and a city

McCormick Place

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
Navy Pier featuring a sunset and rides

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

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

Chicago Riverwalk

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
Six Flags Great America featuring 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
Grant Park showing a garden and night scenes

Grant Park

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_UnitedCenter_6064077_01

United Center

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

United Center

 

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

Aerial view of a business district with stores, a church and shopping center in downtown Northbrook, IL.

Northbrook

Aerial View of Baha'i House of Worship in Illinois. High-angle aerial view of the Baha'i House of Worship in Wilmette, Illinois, surrounded by lush greenery, gardens, and urban landscape.

Wilmette

Chicago which includes a high-rise building and a city as well as a family

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 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.