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Winnetka

Winnetka, IL , USA

Winnetka

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Winnetka

Get ready to fall in love with Winnetka, Illinois! Stroll along tree-lined streets, where charming boutiques and cozy cafés beckon. Feel the sand between your toes at the picturesque beaches of Lake Michigan. Don’t miss the vibrant farmers' market and enchanting homes that whisper stories of yesteryear. This delightful town is a perfect blend of quaint and chic—come explore!

From the Community

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katherinebeard
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ritakovtun

Recommendations

Outdoor4.6/5

Elder Lane Park/Beach

Outdoor4.6/5

Tower Road Park/Beach

Outdoor4.7/5

Lloyd Park and Stepan Family Boat Launch at Lloyd Beach

Outdoor4.6/5

Maple Street Park/Beach

Outdoor4.7/5

Hubbard Woods Park

Outdoor4.5/5

Dwyer Park

Outdoor4.2/5

Happ Road Park

Outdoor4.4/5

Indian Hill Park

Outdoor4.6/5

Nick Corwin Park

Outdoor4.6/5

Village Green Park

Outdoor4.7/5

Skokie Lagoons

Explore the enchanting Skokie Lagoons in Glencoe, IL! This scenic oasis offers winding trails perfect for hiking or biking, stunning wildlife for the curious observer, and calm waters for canoeing adventures. Pack a picnic, soak in the sun, and let the lush greenery transport you to a nature paradise just outside the hustle and bustle of Chicago!

Self Care4.5/5

Community House Winnetka

Nestled in the heart of Winnetka, Community House offers a vibrant hub for local events, art, and wellness programs, making it an iconic destination for residents and visitors seeking connection and community.

Culture4.7/5

Winnetka Public Library

Landmark4.8/5

Music Institute of Chicago

Landmark

Anita Willets Burnham Log House

Transport4.7/5

Winnetka

Transport4.1/5

Hubbard Woods

Landmark4.8/5

Winnetka Farmers' Market

Shop4.6/5

Randoons

Shop4.3/5

Maze Home

Things To Do
Provided byViator

5/5
2 h

Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's where we step in to assist. Your Private Chicago Scenic Driving Tour will start by meeting our knowledgeable Guide/Driver who will pick you up at your hotel or other location provided and then proceed with the exploration of the beautiful windy city.

$315.00
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5/5
3 h

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigley Field exterior (Ferris Bueller's Day Off), the Chicago Board of Trade exterior (The Dark Knight), Union Station's staircase (The Untouchables), and Millennium Park's Cloud Gate (Source Code). Enjoy a seamless and comfortable experience exploring these famous sites.

$315.00
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5/5

Private City Tour 6-10ppl

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

$770.00
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5/5
2 h

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on open-top buses while enjoying engaging audio commentary that reveals the rich history and culture of the Windy City. This tour includes admission to the stunning 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center, offering breathtaking panoramic views of Lake Michigan and the city skyline. - Unlimited hop-on hop-off access for 48 hours across top Chicago attractions - Audio commentary in multiple languages covers local history and culture - Admission to the 360 CHICAGO Observation Deck for breathtaking views - Perfect for first-time visitors, families, and those seeking flexible exploration Time selected at booking is for 360 CHICAGO admission. Big Bus Hop-on Hop-off Tour available anytime during operating hours.

$84.00
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5/5
4 h

4-Hour Chicago City Tour by SUV

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

$800.00
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5/5
6 h

Chicago 6-Hour City Tour by Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

$960.00
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5/5
168 h

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover. Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket! Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules. Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids. Get Started: 7 Days of Premium Access available instantly for iPhone and Android.

$11.75
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5/5
6 h

Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in a spacious, air-conditioned vehicle, and let your friendly local guide show you the city’s most iconic sights and hidden gems. See top landmarks like Millennium Park, Cloud Gate (The Bean), Buckingham Fountain, the Chicago Cultural Center, and Wrigley Field, while discovering vintage architecture, vibrant neighborhoods, and photo-worthy murals along the way. This experience is fully private and customizable, giving you plenty of time for photos, exploring, or grabbing lunch at a local favorite. With insider stories, scenic stops, and seamless transportation, it’s the perfect way to see Chicago in one unforgettable day.

$750.00
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5/5
4 h

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

$179.00
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5/5

Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!

$465.00
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5/5
1 h 30 mins

The Serial Killer & Iconic Chicago Landmarks Bus Tour

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous past as you explore the sites connected to America’s most notorious serial killers — John Wayne Gacy, the “Killer Clown” who haunted the Chicago area, and Jeffrey Dahmer, whose gruesome acts shocked the nation.

$42.00
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4.9/5
4 h 30 mins

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Taste all of Chicago’s classic eats on this 4 1/2 hr Adults-only guided food & bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s first city bike tour company, on this exciting & informative adventure which recently ranked Top 20 Food Tours in the World by TripAdvisor. The journey is a leisurely paced 13mi & includes deep dish pizza, Chicago-style hot dog, Italian Beef, & dessert. Upgrade to sample local craft beer! On the DAY version of bike tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the NIGHT bike tour, you'll ride through the major downtown attractions & see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of Chicago, even if you only came for the food.

$89.00
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4.9/5

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

$539.00
More
4.9/5
3 h 30 mins

Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

$89.00
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4.9/5

Trickery Chicago Magic Show

Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious. Theater is located at 3453 N Halsted Street (near the SE corner of Cornelia Ave). Door opens 15 minutes before showtime and seating is general admission. Venue is BYOB for guests 21+. Cups and bottle openers are available if needed. We do not stock ice but there is a 7-Eleven just down the street (3407 N Halsted). Performance runs approximately 1 hour.

$41.00
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4.8/5
45 mins

Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. The price is the total for all 3 passengers (saving you money compared to other operators who charge per person.)

$849.00
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4.6/5

Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable experience, customizable from 2 to 8 hours. From the iconic skyline to hidden gems off the beaten path, I’ll take you on a journey that captures the heart and soul of this incredible city. I’ll also capture professional photos along the way, so you can take home memories of your adventure. With flexible pickup options, including quick tours during layovers at O'Hare, I make it easy to see the best of Chicago, no matter how much time you have. Book your tour today and let me show you the Windy City through the eyes of a local!

$199.00
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4.5/5
4 h 30 mins

Small-Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighborhoods in Chicago. Some tours show 1 or 2 neighborhoods, we travel through the South Side, North Side, Southwest, Northwest and a portion of Downtown showing more then 10 neighborhoods and attractions.

$125.00
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4.3/5

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

Experience a global adventure without leaving Chicagoland! This tour blends rich cultural landmarks, stunning natural beauty, and nostalgic favorites, creating a one-of-a-kind experience. *Hotel Pickup at 9am 1. BAPS Shri Swaminarayan Mandir– Step into an architectural masterpiece often called the "Taj Mahal of Illinois." 2. Leaning Tower of Niles– A mini replica of the Leaning Tower of Pisa. 3. Westfield Old Orchard Center– Enjoy one hour of shopping and lunch at one of the most beautiful open-air mall. 4. Bahá’í House of Worship– A spiritual and architectural wonder, one of only eight in the world. 5. Scenic Drive Along North Sheridan Road 6. Home Alone House– Visit the iconic film location, a nostalgic stop for movie lovers in the North Shore's wealthy neighborhood. 7. Chicago Botanic Garden– Marvel at springtime tulips like the Netherlands or unwind in the serene Japanese Garden, an oasis year-round. 8. Hotel Drop Off or Drop Off at Navy Pier

$269.00
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4/5

Luxury SUV 4 Hour Sightseeing Tour

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and renowned stadiums. Whether you’re attending a concert, exploring historic sites, or enjoying a day at the park, our professional chauffeur service ensures a seamless and luxurious journey. With our SUV tours, you'll have the flexibility to explore at your own pace. Visit top attractions like Millennium Park, the Art Institute of Chicago, and the Field Museum. Enjoy a thrilling game at Wrigley Field or United Center or take in a concert at Allstate Arena. Our chauffeur will drop you off and pick you up at each location, providing you with the utmost convenience. Book your tour today and let us take care of the details. Travel in comfort and make the most of your time in Chicagoland with our premium SUV tour service.

$350.00
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