Here are some of the best 36 tours and sightseeing options you have while in Chicago.
Tour Images Tour Name Tour Type Tour Details Booking
Chicago CityPass Sightseeing Tickets & Passes Chicago CityPASS is the best deal in the Windy City, giving you discounted admission to five of the city's premier attractions. The Chicago CityPASS ensures you'll get the most out of your vacation - yet it is so compact it will fit into your back pocket. It's all you need to see the best of Chicago! 
Chicago City Hop-on Hop-off Tour Tours & Sightseeing See all the sights of Chicago at your own pace! On a Chicago City Hop-on Hop-off Tour you can get off the bus at any scheduled stop to visit Chicago's most popular attractions, then pick up the tour where you left off or get on at any other regular stop on the route. For individuals and families, this is the best way to see the sites in a day!
Downtown Chicago Deco Cultural & Theme Tours Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour. Learn of Chicago's influence on the international Art Deco movement, and trace the history of lively architectural heritage.
Historic Chicago Loop Skyscrapers Cultural & Theme Tours Perhaps Chicago's most identifiable claim to fame resides in its architecture. The prototype of the modern industrial metropolis arose from the charred landscape left by the Great Fire of 1871. Many of Chicago's surviving buildings are the forefathers of the great modern skyscrapers and on this walking tour you will discover the historic beginnings of the Chicago School of Architecture and the earliest skyscrapers, built between the 1870s and the 1930s.
Modern Chicago Loop Skyscrapers Cultural & Theme Tours Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles that incorporate new, environmentally-sustainable technology. A great 2 hour tour for architecture buffs as well as anyone with a simple interest in the buildings of Chicago.
Tiffany on Wednesdays Cultural & Theme Tours This tour explores the art glass designed, crafted or installed by the Tiffany Glass and Decorating Company, Louis Comfort Tiffany and his contemporaries, in four late 19th Century Chicago landmarks:
Chicago Airport Arrival Transfer Transfers & Ground Transport Don't want to queue for a taxi or battle unfamiliar streets in a rental car? Save time and money with the convenience of a pre-paid shuttle transfer to downtown Chicago hotels.
Chicago Airport Roundtrip Transfer Transfers & Ground Transport Travel in comfort from the airport to your downtown Chicago hotel and back again with a Chicago Airport Roundtrip Transfer. Take the hassle out of your holiday with the convenience of a regularly scheduled transfer service to downtown Chicago.
Chicago Airport Departure Transfer Transfers & Ground Transport Don't pay high cab fares or struggle with luggage on public transport, a Chicago Airport Departure Transfer is the easiest way to make it to the airport for your flight on time, every time.
Chicago Lakefront Neighborhoods Bicycle Tour Walking & Biking Tours Accept no imitations! This tour taking you off the tourist beat and onto the quiet neighborhood streets, city parks, and packed beaches of the North Side of Chicago, giving you a glimpse as to how Chicagoans enjoy their beautiful city. This tour is for all ages and fitness levels
City Lights at Night Bicycle Tour Walking & Biking Tours Bike through Chicago's most attractive locations at night and discover her charming neighborhoods. Enjoy a leisurely and informative biking experience as you see some of the most beautiful sites of the Windy City such as Buckingham Fountain, Millennium Park and Museum Campus. As you cruise downtown, you'll see Chicago illuminated with the sparkling city lights on this night bicycle tour.
Chicago Segway Tour Tours & Sightseeing Hop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham Fountain, Navy Pier, Lake Michigan and more. Be one of the first to take part in this unique, unforgettable experience!
Chicago Segway Night Tour Tours & Sightseeing Hop on the most innovative tour to hit Chicago in years! Gliding through the Windy City on an eco-friendly Segway is the coolest ride of the 21st century! Far easier than walking, and more unique and personalized than a coach tour, riding a Segway personal transporter is a once-in-a-lifetime experience.
Shopping Tour to Aurora Chicago Premium Outlets Shopping & Fashion Head to Chicago Premium Outlets for an unparalleled collection of 120 designer and name brand stores offering savings of 25% - 65% every day!
Chicago Club Crawl Food, Wine & Nightlife After dark, hit two of Chicago's hotspots for the best in blues and late night entertainment. At each club you will be treated to some of the City's popular Blues artists and entertainers. Transportation, admission and a drink (beer or wine) will be included at each club.
Chicago Grand Half-Day Tour Tours & Sightseeing This comprehensive half-day tour is the perfect introduction to the Windy City. From the highlights of the North Side and South Shore, to driving virtually the entire length of the scenic Outer Drive, you'll come away with an overview of the best Chicago has to offer.
Chicago Grand Tour and Hancock Observatory Sightseeing Tickets & Passes Enjoy the Grand Tour of Chicago and a visit to the Hancock Tower! See the sites from one of Chicago's tallest landmarks.
Chicago North Side Tour Tours & Sightseeing This is the tour for those looking to experience the vitality and excitement of Chicago. You'll tour through Chicago's main business section, one of the financial centers of the world and always bustling with activity. You'll tour the famous "Loop" and State Street - the great street where Chicago's fame began.
Chicago South Shore Tour Tours & Sightseeing Here is a tour full of interest, history, and beauty. You'll travel through Grant Park, the front lawn of the city and site of Soldier Field, Adler Planetarium with its sky dome, the Joseph Petrillo outdoor band-shell where Chicagoans listen to fine music throughout the summer nights, the Art Institute of Chicago, world renowned for the largest collection of impressionistic art, Orchestra Hall, home of the famous Chicago Symphony Orchestra, the world's largest aquarium, the Shedd Aquarium, and the Field Museum of Natural History, renowned for the size and scope of its collections. And looking over from these sights you'll see the 80 story Amoco Oil Building, completely faced in white granite. Then you'll travel through the South Commons a new 'close- in' residential community. Upgrade and add a guided cruise on Lake Michigan.
Chicago Hop-on Hop-off Trolley and Upper Decker Tour Tours & Sightseeing Enjoy a scenic tour of Chicago's lake front and downtown area aboard the Trolley buses and the New Upper Deckers!
Tommy Gun's Garage Dinner and Show Food, Wine & Nightlife Welcome to the only speakeasy dinner show in Chicago Tommy Gun's Garage! Just say the password and you'll be transported back to the roaring twenties. You'll be entertained by gangsters and flappers, dancing the Charleston to the music of Cole Porter and George Gershwin. It's a night out in Chicago you'll never forget!
Go Chicago™ Card Sightseeing Tickets & Passes The Go Chicago Card is the perfect way to save on your Chicago vacation. You'll get FREE admission to over 25 attractions and tours for one low price! Chicago has dozens of great attractions, so the Go Chicago Card has something for everyone.
Chicago Shopping Tour: Bucktown and Wickerpark Shopping & Fashion Explore Chicago's hippest shopping neighborhoods - Bucktown and Wickerpark. Your shopping guide will take you to the neighborhoods' most unique boutiques where you can find up-and-coming designers and the latest fashion trends. This unique Chicago Shopping Tour leads you to all the hard-to-find boutiques that you won't find back home or on the Magnificent Mile.
Chicago Shopping Tour: Lincoln Park Shopping & Fashion Explore Chicago's prettiest shopping neighborhood - Lincoln Park. Your shopping guide will take you to the neighborhood's most unique boutiques where you can find local designers and all the latest trends. This unique Chicago Shopping Tour leads you to all the hard-to-find boutiques that you won't find back home or on the Magnificent Mile.
Chicago River and Lake Architecture Tour Cruises, Sailing & Water Tours Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all about Chicago's history and landmarks before the tour's grand finale, a thrilling speedboat ride on Lake Michigan.
Chicago Brunch Cruise Cruises, Sailing & Water Tours Experience Chicago's amazing skyline views from a unique vantage point on board this unforgettable 2 hour brunch cruise. With unsurpassed views of the Sears Tower, the John Hancock Tower, to the Museum campus and the Aon Center, you'll be seduced by the luxury and spaciousness of the three climate-controlled dining and observation decks while sailing on the world-famous harbor.
Chicago Dinner Cruise Cruises, Sailing & Water Tours Step aboard the Chicago Dinner Cruise and enjoy a three-hour escape on Lake Michigan. Relaxing in the elegant ambiance that only a true luxury cruising vessel can provide, you'll sail along the lake shore and have unmatched views of the world-famous Chicago skyline.
Chicago Halloween Haunted Cruise Holiday & Seasonal Tours Add a new adventure to your Halloween festivities this year. Come join all the fun on a haunted one hour speedboat cruise on Lake Michigan.
Chicago Lunch Cruise Cruises, Sailing & Water Tours Welcome aboard Chicago's largest luxury yacht at Navy Pier! Tantalize your taste buds and discover Chicago's wonderful city skyline on this two-hour lunch cruise. While you cruise, and enjoy a freshly prepared three-course meal, you'll enjoy magnificent views of the Windy City skyline and hear your favorite music from a live trio.
Lake Michigan Speedboat Ride Water Sports Feel the need for speed? This exhilarating speedboat ride takes you out onto Lake Michigan for the ride of a lifetime. Experience the roar of the 2000-horsepower engines as you race along Chicago's famous Lake Michigan. The best way to view Chicago is always from the lake!
LEGOLAND Discovery Center Chicago Family Friendly LEGOLAND? Discovery Center, a giant indoor LEGO world designed for families with children aged 2 to 12, is located in Schaumburg's Streets of Woodfield shopping center. The 30,000-square-foot attraction features activities ranging from hands-on LEGO play to life-sized LEGO adventures designed to provide several hours of family entertainment centered around the iconic interlocking colored bricks.
Chicago Party Pass Food, Wine & Nightlife Purchase the Chicago Party Pass and party like a VIP at 11 of the Hottest Nightclubs in Chicago. Receive special offers such as: Free Entrance, No waiting in line and a free drink at each nightclub.
Adler Planetarium and Astronomy Museum Sightseeing Tickets & Passes Be transported to the outer reaches of the Universe on a visit to Chicago's Adler Planetarium and Astronomy Museum, the first planetarium in the United States. Since 1930 the country's oldest planetarium has been delighting audiences with the spectacle of the night sky. Visit the Atwood Sphere Experience, Shoot for the Moon exhibit and choose from a range of five Sky Shows at the Definiti Space Theater or 3D Universe Theater.
Historic Hyde Park and Kenwood Mansion Bicycle Tour Walking & Biking Tours See the neighborhoods of Chicago on the Historic Hyde Park and Kenwood Mansion Tour. This 4-hour, 24-mile (38 km) bike ride is perfect for moderate to advanced riders and a great way to explore Chicago.
Chicago Segway Art & Architectural Tour Tours & Sightseeing See Chicago?s landmark architecture, outdoor sculptures and famous skyline by Segway! This family-friendly guided tour is both an exciting and educational way to explore Chicago. Plus, you'll save your feet from a day of walking and instead, quickly glide along the lakefront soaking in views of the spectacular skyline while seeing some of the tallest buildings in the world.
Chicago Sunset Dinner Cruise with Buffet Cruises, Sailing & Water Tours Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like Navy Pier, Soldier Field and more while you dine on a lavish, all-you-can-eat buffet! See spectacular views of the Chicago skyline while being entertained by a singing ship staff and a live DJ spinning your favorite songs.