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Top Illinois Sightseeing Tours
Chicago Architecture River Cruise
1 hour 15 minutes - Experience one of the world’s most beautiful cities on a cruise down the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see...Read more
Chicago's Gold Coast Hidden History: A Self-Guided Audio Walk
50 minutes - Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss, takes you on a fascinating self-guided audio tour of hidden historical spots in Chicago's gilded Gold Coast. Peep behind the gates of the original Playboy Mansion, walk along a wooden block-paved alley, sip a Faster Pussycat in Chicago's oldest piano bar and more as you enjoy a...Read more
90-Minute Chicago River Architecture Tour
1 hour 30 minutes - Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained...Read more
Lake Michigan Sightseeing Cruise
40 minutes - Admire all of Chicago's fabulous lakefront sights and attractions on this 40 minute Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing views of the city’s famous skyscrapers from a great vantage point. Feel free to bring a lunch and enjoy drinks from the onboard bar as you relax on this sightseeing...Read more
Chicago Lake and River Architecture Tour
1 hour 30 minutes - An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known...Read more
Big Bus Chicago Hop-On Hop-Off Tour
2 hours - The lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of a Classic, Premium or Deluxe ticket, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop...Read more
Gangsters and Ghosts Tour in Chicago
2 hours - Interested in exploring Chicago from the perspective of ghosts and gangsters- Want to really immerse yourself in the history of this great American city, right from the locations that started it all- This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in...Read more
Chicago Lakefront Electric Bike Tour
1 to 2 hours - This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will get a chance to ride Electric Bikes and see the city from a different vantage point.
It all begins navigating through Buckingham Fountain, the Art Institute of Chicago, and the Museum...Read more
1-Day Harley-Davidson Museum+Lake Geneva (Chicago Departure) CW1
8 to 10 hours - Itinerary:
Milwaukee - Harley-Davidson Museum (Optional, 75 mins) -Miller Brewery (Optional, 75 mins) - Lake Geneva - Lake Geneva Bay Cruise (Optional, 60...Read more
Famous Tastes of Chicago Food Tour
3 hours - What should a visitor see and do while in Chicago- It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond that it can often be hard to decide where to start. Why not tantalize all of your desires and senses with a 3 hour small- group walking food excursion lead by a professional guide- You'll...Read more
Chicago Style Food Tour
3 hours - Confused on what to see and do while in Chicago- It goes without saying that the Windy City has it all; from food, history, architecture, culture and beyond. Combine them all by tantalizing all of your senses with a 3 hour small- group walking food excursion lead by a professional guide. You'll indulge in 5-6 of Chicago's quintessential staples...Read more
Amazing Lakefront Segway Tour in Chicago
2 hours 30 minutes - Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a...Read more
Chicago Crime and Mob Bus Tour
1 hour 30 minutes - Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Walking tour paths explore historic crime scenes with great photo opportunities. True crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap...Read more
Holiday Hike Chicago-Style: Festive Food & Walking tour
3 hours - There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3-hour guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for tours by bike and on foot. You’ll get to sample the Windy City’s favorite winter treats; including a...Read more
Chicago Fireworks Dinner Cruise with Buffet
3 hours - 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 and a live DJ spinning your favorite songs. In the summer...Read more
Private Chicago Highlights Driving Tour
3 hours - See Chicago’s most essential landmarks from the comfort of a private vehicle on this 3-hour jaunt around town. Your guide will pick you up directly from your Chicago accommodation, after which you’ll be whisked away to see the sights. From the storied Magnificent Mile to the glamour of the Gold Coast, you’ll encounter the best of the Windy...Read more
Chicago Favorites Ultimate Food & Walking Tour
3 hours - Stroll through the beautiful streets of downtown Chicago and taste all of the Windy City’s favorite eats! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, whose walking tours have been recognized nationally by National Geographic, USA Today, and Conde Nast Traveler Magazine. This is Bobby’s quintessential culinary...Read more
Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
4 hours - Taste all of Chicago’s classic eats on this four-hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure. The journey is 14 miles (traversed at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot...Read more
Private Haunted History of Chicago Ghost Tour
3 hours - Up for more of a spooky perspective of the Windy City- Boy, does it deliver. We have curated a unique and underground ghost tour, providing you with the rare opportunity to visit many of Chicago’s notable haunted locations.
• Murder Castle: the hotel designed specifically for murdering people in the late 1800s by America’s first mass...Read more
Chicago Sunset Segway Tour
2 hours 30 minutes - Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views as well as views of Chicago's world-famous skyline and graceful lakefront. This segway tour departs near Millennium Park as dusk arrives and passes sights like Buckingham Fountain,...Read more