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525 Available Tour Excursions in Chicago
The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!
Price: $89.00
Duration: 2 hours
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.
Price: $507.96
Duration: 2 hours
This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with varying architectural styles and see how older structures connect to new skyline additions. On this tour, we'll make seven stops in downtown Chicago where we can compare the histories and styles of buildings located within sight of each other. The tour features 19th-Century Commercial, Beaux-Arts, Mid-Century Modern and Postmodern buildings, as well as the latest in architecture from Frank Gehry, Renzo Piano and Adrian Smith. At each stop, we’ll look at the connections between the past and present and discover what inspires design today. The tour culminates with a visit to Millennium Park, where world-class art and architecture combine, creating a unique urban fabric. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Price: $35.00
Duration: 1 hours
Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supernatural speakeasies. Whether you’re a recent transplant to Chicago or have lived among the Windy City’s ‘others’ for years, you’re about to get a haunted history that may leave you with more memories than you dare to retain. Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago. A costumed guide will lead tour goers on a walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
Price: $34.77
Duration: 1 hours
This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which provides a unique and interesting touch to the normal tour experience. Being both sturdy in the water, and fast! Reaching up to speeds of 35 Knots! We work hard to provide historical context for our great city, as well as provide an exhilarating experience through the use of high speed runs and spins!
Price: $90.00
Duration: 1 hours
We’ll begin our photo walk in Millennium Park with portraits at Cloud Gate (The Bean), one of Chicago’s most iconic landmarks. During our time together, we’ll visit a rooftop spot for skyline views, cross the scenic DuSable Bridge, and stop by the elegant Wrigley Building - all perfect for beautiful photos. Along the way, I’ll guide you with natural poses and creative ideas, helping you feel relaxed and confident. By the end of this walk, you’ll not only have a beautiful photo gallery - you’ll have also visited many of the MUST-SEE places in downtown Chicago.
Price: $169.00
Duration: 1 hours
Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became a global force in culture, commerce, and architecture. Our tour will explore building interiors like the world's oldest skyscrapers, City Hall, the underground Pedway, and the old library. We will observe public art like the Picasso and the Bean. While immersed in the places where it happened, Chicago's colorful stories will vividly spring to life. This walking tour aims to enhance your understanding of modern-day Chicago by a deep dive exploration of its history. Your guide to the city is the friendly and well-informed Dave Lineal: local artist, culture vulture, and historian. Dave is tested and certified by the Chicago Tour-Guide Professionals Association. This is an outdoors / indoors all-weather walking tour with a duration of two hours. We will meet under the marquee at the Chicago Theater, 175 N. State Street.
Price: $33.00
Duration: 2 hours
Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life through captivating stories, insider insights, and exclusive information tailored to your interests.
Price: $162.50
Duration: 2 hours
Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from early, classically inspired European styles to bold American Art Deco and Modernist innovations to today’s Contemporary designs that continue to set the pace for world-leading architecture. As you journey through Chicago’s spectacular skyscraper canyons and stunning interiors, you’ll see how economics, technology, creativity, and gritty determination shaped Chicago’s ever-evolving skyline. Whether you’re a visitor or you’re a Chicagoan who has never explored the architectural masterpieces you see every day, join us today on this enlightening adventure.
Price: $35.00
Duration: 1 hours
Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At the museum, visit the Butterfly Haven and Birds of Chicago exhibit; admission is included. Walk through Victorian-style greenhouses with orchids and tropical palms, and see zoo habitats while hearing conservation stories from your guide.
Price: $274.98
Duration: 2 hours
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.
Price: $315.00
Duration: 2 hours
Chicago’s top-rated limo and car service — with 16+ years of proven service, licensed drivers, and full commercial insurance. Enjoy a safe, private transfer between Midway Airport (MDW) and any destination within Chicago city limits. All chauffeurs are fully uniformed, background-checked, and trained for professionalism and safety. Vehicles are equipped with GPS tracking and dispatch monitors every trip. Upon arrival, you’ll receive a text with your driver’s details. At the airport, meet your driver curbside after exiting baggage claim. Skip the hassle of taxis, shuttles, or rideshares — and travel in a clean, comfortable, late-model private sedan. Ideal for business or leisure travelers, solo riders or families. 24/7 support. Chicago-based and proud to be a 5x Certificate of Excellence winner on TripAdvisor. Reliable. Professional. Local.
Price: $160.00
Duration:
Skip the stress of a taxi or shared shuttle between Chicago downtown and Midway airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel.
Price: $142.00
Duration:
#1 Rated Car Service In Chicago Area based on 400 + combined reviews on Trip Advisor, Google and Yelp. We carry newer model luxury vehicles with low mileage and professional, uniformed chauffeurs. Skip the stress of a taxi or shared shuttle between Chicago downtown and O'Hare airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick-you up in Chicago and drop you off at O'Hare Airport. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago O'Hare Airport with this private transfer service.
Price: $133.00
Duration:
Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn from expert guides what makes Chicago one of the spookiest places in the world! Note, tour does not finish where it starts
Price: $35.00
Duration: 1-1 hours
Enjoy a fun and scenic 90-minute Cycleboat Cruise along the beautiful Chicago River! Take in stunning skyline views as you pedal, relax, and sip your favorite drinks with friends, family, or that special someone. • 1.5-hour cruise up and down the iconic Chicago River • Comfortable boat with 10 cycle stations and bench seating at the front • Maximum capacity of 16 passengers — perfect for smaller groups or couples • BYOB! Bring your own beverages and snacks to enjoy onboard • Departs from the Water Plaza on the Chicago Riverwalk (between Wells Street and LaSalle Street bridges) Whether you want a lively group outing or a relaxing ride through the city, this Cycleboat Cruise is one of the most unique ways to see Chicago from the water — no full-boat rental required!
Price: $65.00
Duration: 1 hours
- Chicago's Highest Rated Limo And Car Service - 16 Years in the limousine business - Proven track of exceptional customer service - Professional, Safe, Fully Uniformed Chauffeurs - FBI Background checks for all drivers - $350,000 Commercially Insured - GPS tracking devices on all vehicles - "Driver ON Location" automated text message - Chicago Based company Skip the stress of a taxi or shared shuttle between Chicago downtown and O'Hare airport with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago O'Hare Airport with this private transfer service.
Price: $175.00
Duration:
Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazing area, the most desirable address in the city before the fire. Many of the incredible homes are still standing and the spirits linger, waiting to divulge their secrets in a haunted history tour and ghost investigation in one of Chicago's most prestigious places.
Price: $39.99
Duration: 2 hours
Key Info for Visitors
- Currency: USD
- Languages: English, Spanish, Polish, Chinese
- Climate: Continental
- Timezone: America/Chicago
- Population: Approximately 2.7 million
- Best Time to Visit: best time to visit is late spring to early fall to enjoy pleasant weather.
- Visa Requirements Visitors to Chicago generally follow U.S. visa requirements. Citizens from visa waiver countries such as most EU nations, the UK, Canada, Australia, and Japan can enter the U.S. for tourism without a visa for up to 90 days under the ESTA program. Other travelers may need to apply for a visa in advance. U.S. citizens do not require a visa. Visitors should check the latest U.S. Department of State guidelines for specific visa categories, e-visa options, and entry requirements.
About Chicago
Chicago is a dynamic city renowned for its striking skyline, rich cultural heritage, and vibrant urban life. Nestled on the southwestern shore of Lake Michigan, it offers a unique blend of architectural marvels, world-class museums, and diverse neighborhoods. Visitors are drawn to Chicago’s iconic deep-dish pizza, jazz and blues music, and its status as a hub for arts and theater. The city’s lakefront provides scenic parks and beaches, perfect for outdoor activities. Chicago’s history as a center of industry and innovation is reflected in its museums and historic sites. The city’s friendly Midwestern vibe combined with cosmopolitan amenities makes it a compelling destination for travelers seeking culture, cuisine, and entertainment. Whether exploring the Magnificent Mile, catching a show in the Theater District, or enjoying a boat tour on the Chicago River, visitors find plenty to inspire and entertain.
Chicago Tours & Experiences
- Top Attractions: Highlights of Illinois
- Duration Range: 2 to 10 hours
- Group Size: Private or shared tours
- Difficulty Level: Mixed Difficulty
- Recommended For: The best time to visit is late spring to early fall to enjoy pleasant weather. Pack layers as temperatures can vary. Chicagoans are friendly but direct; tipping 15-20% in restaurants is customary. Stay vigilant in crowded areas and avoid poorly lit neighborhoods at night. Credit cards are widely accepted, but having some cash is useful. Plan visits to popular sites in advance to avoid long lines.
Average Tour Price: $95
Lowest Price Tour: $50
Highest Price Tour: $220
Important Tour Information
- Bring comfortable walking shoes and appropriate clothing
- Check tour cancellation and refund policies
- Arrive at the meeting point at least 15 minutes early
- Carry valid identification and tour booking confirmation
Frequently Asked Questions
Local Food & Cuisine
Chicago’s food scene is famous for its hearty deep-dish pizza and Italian beef sandwiches. The city also offers a rich variety of international cuisines reflecting its diverse population, including Polish, Mexican, and Chinese dishes. Must-try foods include Chicago-style hot dogs and Garrett Popcorn. Noteworthy restaurants include Alinea, known for innovative fine dining, and Lou Malnati’s for classic deep-dish pizza.
Getting Around
Chicago is accessible via O’Hare International Airport and Midway Airport, both well-connected globally. The city has an extensive public transit system operated by the CTA, including buses and the 'L' train network, which is convenient and affordable for getting around. Taxis and rideshares are widely available. Walking is practical in downtown areas. Costs vary, but a single CTA ride is economical, and multi-day passes are available for tourists.
Travel Tips
The best time to visit is late spring to early fall to enjoy pleasant weather. Pack layers as temperatures can vary. Chicagoans are friendly but direct; tipping 15-20% in restaurants is customary. Stay vigilant in crowded areas and avoid poorly lit neighborhoods at night. Credit cards are widely accepted, but having some cash is useful. Plan visits to popular sites in advance to avoid long lines.
Culture & Customs
Chicago’s culture is a blend of Midwestern friendliness and urban sophistication. Social interactions tend to be polite but straightforward. The city hosts major events like the Chicago Blues Festival and Taste of Chicago food festival. Sports are a big part of local culture, with passionate fans of baseball, basketball, and football. Respect for diversity and community pride are important local values.
About The Author
Calvin has loved travel and adventure since first visiting Los Angeles with a suitcase in 1992 at the age of 20. He ditched the suitcase and got a backpack pretty fast.
He hates leaving after any trip and has to console himself by writing and sharing articles on it. You can find and connect with him on linked in here.
Likes
Travel, Gaming, Scuba Diving, Skiing and anything to do with water.
Dislikes
Exact luggage sizing police and being tired in an airport and many more..