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Illinois Tours
All Illinois Tours & Excursions in 2026 - page 22
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500+ results
Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Englewood, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Englewood - Led by knowledgeable Historian Dilla for an authentic experience
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2 Hour Englewood, Chicago Tour
2 hours
Free Cancellation
from
US$45
Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like North Lawndale, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in North Lawndale - Led by knowledgeable Historian Dilla for an authentic experience
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2 Hour North Lawndale, Chicago Tour
2 hours
Free Cancellation
from
US$45
Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic skyscrapers and stunning lobbies, learning the fascinating stories behind their designs. This 2.5-hour tour is perfect for architecture enthusiasts and curious travelers alike, providing a unique perspective on the birthplace of modern skyscrapers. Whether you’re a local or a visitor, discover why Chicago's skyline is renowned worldwide. - Private tour lasting 2.5 hours, perfect for families and small groups - Visit landmark buildings like The Sullivan Center and The Rookery - Expert local guide shares insider knowledge about architectural history - Flexible meeting points available for your convenience
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Private Chicago Loop Architecture Walking Tour
2 hours to 2 hours 30 minutes
Free Cancellation
5.0
(529 Operators)
from
US$180
Price varies by group size
Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walking tour circles Wicker Park, showcasing stunning Victorian mansions on Beer Baron's Row while sharing engaging trivia about the area’s rich ethnic and commercial history. Enjoy insights into the local arts and entertainment scene and uncover the best spots to eat and drink along the way. Test your knowledge with trivia, and compete for a special prize at the end of the tour. - Explore the historic Wicker Park neighborhood on foot - Visit iconic locations like the Polish Triangle and Beer Baron’s Row - Engage in neighborhood trivia for a chance to win a prize - Learn about the area's ethnic history, arts scene, and dining hotspots
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Wicker Park Walking Tour History Trivia and Local Flavors
1 hour 30 minutes to 2 hours
Free Cancellation
5.0
(1)
from
US$40
Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your steps in" along the scenic Riverwalk, revealing the stories behind the city’s most celebrated structures. Expert guides will share insights into the work of renowned architects like Mies van der Rohe and Jeanne Gang, showcasing the stunning interplay of glass, steel, and water. Ideal for architecture enthusiasts and first-time visitors alike, this tour offers a unique perspective on the Windy City’s vibrant culture and architectural beauty. - Discover Chicago’s architectural evolution from Art Deco to modern designs - Guided insights from experts on legendary architects and their masterpieces - Enjoy a scenic stroll along the picturesque Riverwalk - Perfect for both architecture lovers and those new to Chicago
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Chicago Riverwalk Architecture Walking Tour and Discover Skyline
1 hour 30 minutes
Free Cancellation
from
US$49
Likely to Sell Out
This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks and hidden streets, capturing the city’s character from golden hour through to its dazzling night lights. As skyscrapers glow and trains blur past, your professional guide helps you master techniques like composition, long exposure, and low-light shooting. Designed around your skill level, this private tour ensures one-on-one coaching, creative development, and unique photo opportunities. It’s more than sightseeing—it’s a hands-on journey through Chicago’s streets after dark, where every corner becomes a chance to create striking images. Creative composition, using lines, repetition, camera angles Training your eye: finding subjects, lighting, composition Taking control of your camera: f-stop, shutter speed, ISO and focusing Reviewing your photography
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Chicago Photography Masterclass Private Photography Lesson
3 hours
Free Cancellation
from
US$140
Price varies by group size
Special Offer
The Neo-Futurists are a landmark American theater company, making high-energy, honest, and strange work for the past 38 years. Our flagship show THE INFINITE WRENCH is never the same twice, and changes drastically from week to week.
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The Infinite Wrench: Experimental theater in Chicago
1 hour 20 minutes
Free Cancellation
4.5
(29 Operators)
from
US$20
US$16
Enjoy a serene evening on Lake Michigan with a private sunset sailing charter, where the stunning Chicago skyline transforms as the sun sets. Departing from Montrose Harbor, this exclusive experience offers a cozy atmosphere for date nights, anniversaries, and memorable celebrations. Aboard the Vagabond, a Beneteau Oceanis 393 yacht, guests can unwind, capture picturesque moments, and savor their favorite BYOB drinks and snacks against the backdrop of golden-hour light. With a dedicated captain overseeing your journey, relish a tranquil escape just minutes from the bustling city.
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Private Chicago Sunset Sailing Charter on Lake Michigan
3 hours
Free Cancellation
4.5
(7 Operators)
from
US$1,350
Per group
Little Diners Crew invites young food enthusiasts aged 4-12 to embark on culinary adventures that expand their palates beyond mac-n-cheese and chicken fingers. Each month, kids explore different cuisines at Chicago's best restaurants while interacting with chefs, tasting and rating new dishes, and learning about food preparation and dining etiquette. Meals become memorable experiences as kids discover the world through food.
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Little Diners Crew Culinary Adventures for Kids
2 hours
Free Cancellation
from
US$105
One of the two remaining founding members of the NFL, dating back to 1920, the Chicago Bears are the epitomise NFL history. For an experience filled with tradition and history, look no further than attending a Bears game at the iconic Soldier Field. The Bears are entering a new era, led by former Heisman-Trophy winning quarterback, Caleb Williams. The excitement and electricity in the air Solider Field is noticeable and expectations amongst the Bears passionate fanbase have been raised. Soldier Field, the oldest stadium in the NFL, is a historic venue, located on the shores of Lake Michigan, with a unique architectural blend of the original structure and modern upgrades. The tailgating scene at Soldier Field is vibrant. Fans gather hours before the game to socialize and celebrate, forming a big part of the game day experience. Attending a game is also an opportunity to explore the city, known for its famous deep-dish pizza, you’ll have to get a taste of the real Chicago culture!
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Chicago Bears Football Game at Soldier Field
4 hours
4.0
(1 Operators)
from
US$419
Likely to Sell Out
Here's what you can expect during your 1.5-hour private room experience: Shooting/Spinning Art Experience: Collaborate with your group to create a masterpiece on a large canvas (24x36 inches) using our unique Shooting/Spinning technique. Each team of seven people will work together to shoot down balloons filled with paint, then watch as we spin your canvas to create mesmerizing abstract art. Art Room Experience: Indulge your inner artist as you each create your own masterpiece on a personal canvas (16x20 inches). Choose your colors, unleash your creativity, and bring your vision to life in our inviting art room. Paint: High-quality acrylic paints provided for all your artistic endeavors. Premium Clothes Protection: Keep your party attire clean and stylish with our premium clothes protection, ensuring a worry-free painting experience. Book your party at Shot of Art today and prepare for an unforgettable experience!
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Art Boom 3 in 1 : Adults-Only Private Art Experience in Chicago
1 hour 30 minutes
Free Cancellation
5.0
(3 Operators)
from
US$195
Likely to Sell Out
Get to grips with Italian pasta in this Florentine-inspired hands-on class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs. Carpaccio, hand-filled ravioli, a fresh vodka sauce and citrus cookies – four courses, four distinct techniques, one deeply satisfying Italian meal. Your hands-on cooking experience features: - Marinated Vegetable Carpaccio – assorted vegetables, homemade herb dressing and fresh herbs - Beef Ravioli – flour, eggs and seasoned beef - Vodka Sauce – olive oil, tomatoes and vodka - Italian Lemon Drop Cookies – flour, butter and eggs You will leave with real pasta-making skills and a fresh perspective on Italian cuisine, from antipasto to dessert. Guests are welcome to bring wine or beer to enjoy throughout the experience.
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Italian Ravioli Cooking Class in Chicago (Includes 4-Course Meal)
2 hours 30 minutes
Free Cancellation
5.0
(10 Operators)
from
US$145
Likely to Sell Out
In the heart of Chicago, near Wrigley Field, a culinary adventure awaits. Led by Rakhi, a professionally trained chef and Le Cordon Bleu graduate with experience working with Bobby Flay, this private cooking class immerses you in the rich flavors of Italian-American cuisine. Over 2.5 hours, you'll learn to prepare iconic dishes such as Chicken Vesuvio, hot fried chicken, and homemade desserts, all while enjoying a relaxed and interactive atmosphere. With the chance to tailor your menu, every class becomes a unique experience that celebrates Chicago's vibrant food culture. Gather your friends or family for a memorable evening of cooking and dining together.
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Private Chicago Cooking Class with Le Cordon Bleu Chef
2 hours 30 minutes
Free Cancellation
4.5
(8 Operators)
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US$149
JT and the team ensures a seamless, guided experience, whether you're a seasoned angler or a first-timer. Enjoy satellite entertainment and hi speed wifi for those last minute video conference calls. Our commitment to comfort, elegance, and excellence sets us apart in every detail. From sunrise departures to golden hour returns, every moment is tailored for exclusivity. Whether you're celebrating a milestone or escaping the ordinary, we make every trip unforgettable. Discover what it means to fish luxuriously—reserve your elite charter today.
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Boating or Fishing Charter Chicago's Lake Michigan
6 hours
Free Cancellation
from
US$1,795
Per group
This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.
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Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour
45 minutes to 1 hour 15 minutes
Free Cancellation
3.0
(6 Operators)
from
US$10
Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your professional chauffeur will navigate the bustling streets of the Windy City. Glance through the panoramic windows at towering skyscrapers like the Willis Tower. Coast down Michigan Avenue to admire the luxury boutiques of the Magnificent Mile. Pass by the architectural marvels of the Loop and the lakefront beauty of Grant Park. This tour itinerary maximizes your time in the city. It is ideal for couples celebrating an anniversary, travelers on a tight schedule, or anyone seeking a VIP Chicago experience. Avoid the crowds of standard tour buses. Enjoy the privacy, comfort, and prestige of DS Luxury Rolls-Royce Tour.
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Downtown Chicago City Tour in a Rolls Royce
1 hour
3.0
(6 Operators)
from
US$195
Special Offer
Get views of Chicago’s most famous buildings, as well as insider info from an expert guide, on this time-saving, architecture-focused cruise. See the city's most important buildings all on one tour—including the Willis (Sears) Tower, Old Post Office, Wrigley Building, and more—and enjoy a more relaxing way to explore the city. As you go, your guide's live commentary will bring their stories to life. This pet-friendly cruise offers accessible boarding from Navy Pier dock only. What's included Guided architecture cruise of the historic Chicago River Live expert commentary on board Restroom on board Pet-friendly What's not included Drinks (available for purchase) WiFi on board Highlights See Chicago's top architectural masterpieces in a single tour Pet-friendly cruise allows you to bring your dog along Learn about the city's architectural history through an expert's narration Admire some of the most picturesque angles of the city
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Chicago Architecture River Cruise
1 hour
Free Cancellation
from
US$67
US$54
Enjoy a stress-free game day with your 5-hour private hourly service. Skip parking hassles and stadium traffic while your professional chauffeur handles the driving. Travel in comfort and style with your choice of Sedan, SUV, Sprinter Van, or Minibus — perfect for groups from 6 to 23 passengers. Your vehicle is exclusively yours for 5 hours, giving you the freedom to make multiple stops, tailgate, or celebrate after the game. With door-to-door pickup from your hotel, residence, or airport, bottled water onboard, and a luxury fleet designed for comfort, you can focus on the excitement of the event while we take care of the rest.
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5-Hour Sports Event Chauffeured Service in Chicagoland
5 hours
Free Cancellation
from
US$500
Per group
The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see landmarks such as the Gold Pyramid House and the stunning Bahāʾī temple. The 85-mile bike ride will bring you right to your boutique inn where your bags will be waiting for you. The following day your guide will take you to the beach where you can kayak or just enjoy some much-deserved lounging. After this you will visit the Apple Barn for a delightful day of seasonal apple or strawberry picking, followed by a stop at their bakery. Don't forget to bring your ID for the wine tasting; they often feature live music and are very family-friendly! Will give you time to explore the shops and ice cream parlors in the charming downtown area before packing the car to drive you back to Chicago.
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Small Group Bike Tours From Chicago to Lake Geneva
2 days
Free Cancellation
from
US$449
Per group
Comfortable Roundtrip Tour from your hotel in Chicago to Lighthouse Place Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.
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Private Shopping Tour from Chicago to Lighthouse Place Outlets
6 to 7 hours
Free Cancellation
5.0
(4 Operators)
from
US$366
Price varies by group size
Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.
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Private Shopping Tour from Chicago to Chicago Premium Outlets
5 to 6 hours
Free Cancellation
5.0
(4 Operators)
from
US$288
Price varies by group size
Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into the city’s architecture, skyline, and history while guiding you to the best photo spots. Begin at Museum Campus, where the skyline rises above Lake Michigan, offering stunning reflections at golden hour. Continue to Adler Planetarium for one of Chicago’s most iconic panoramic skyline views. Visit Buckingham Fountain, where the historic landmark creates a beautiful foreground for sunset photos. Head to North Avenue Beach to capture the skyline stretching across the horizon as the sun sets, then enjoy a scenic drive along Lake Shore Drive as city lights begin to glow. With a flexible itinerary and door-to-door service, this experience offers a relaxed, unforgettable way to capture Chicago’s skyline from day to night.
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Chicago Private Lakefront Sunset and Skyline Photo Tour
2 hours
Free Cancellation
5.0
(2 Operators)
from
US$141
Price varies by group size
Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, including the first Europeans to come through here, the Great Chicago Fire, the origin of the skyscraper, the 1893 World’s Fair, Prohibition and the creation of Millennium Park. Along the way, you’ll discover some of the Loop’s most beautiful interiors, found in buildings that thousands of people walk past every day, completely unaware of what’s inside…And how things created inside those buildings shaped our current world for the better. You’ll hear the stories of the men and women--including Jean Baptiste Point du Sable, Daniel Burnham, Potter and Bertha Palmer, and Muddy Waters--who made Chicago what it is today, and those, like Jeanne Gang, who are defining Chicago’s architectural future.
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Chicago Architecture, History and Culture Loop Walking Tour
3 hours
Free Cancellation
5.0
(2)
from
US$50
Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Chatham, led by Historian Dilla, who uncovers the unique stories and contributions of these communities, providing an authentic experience of Chicago's diverse heritage. Whether you're a history buff or simply curious about local culture, these tours offer fascinating insights into the Windy City's past and present. The tours vary in duration but typically last around 2 hours, making them perfect for a quick but enriching adventure. - Discover the history and culture of Chicago's neighborhoods - Tours available in Chatham - Led by knowledgeable Historian Dilla for an authentic experience
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2 Hour Chatham, Chicago Tour
2 hours
Free Cancellation
from
US$45
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Top Attractions in Illinois
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Attractions
Navy Pier
From US$12
Attractions
Tribune Tower
From US$12
Attractions
Grant Park
From US$12
Attractions
Skydeck Chicago at Willis Tower (Sears Tower)
From US$12
Attractions
Art Institute of Chicago
From US$12
Attractions
Chicago River
From US$25
Attractions
Navy Pier
From US$12
Attractions
Tribune Tower
From US$12
Attractions
Grant Park
From US$12
Attractions
Skydeck Chicago at Willis Tower (Sears Tower)
From US$12
Attractions
Art Institute of Chicago
From US$12
Attractions
Chicago River
From US$25
Attractions
Navy Pier
From US$12
Attractions
Tribune Tower
From US$12
Attractions
Grant Park
From US$12
Attractions
Skydeck Chicago at Willis Tower (Sears Tower)
From US$12
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