Private Sedan Transfer Between O'Hare airport & Downtown Milwaukee WI
Reliable and luxury airport transfers
Best and most professional Chauffeurs in the industry
Up-to-date luxury vehicles
High quality of service
Smart rates
Duration: 1 hr 15 min – 1 hr 40 min
- Free cancellation
- Private tour
Private Chicago Street Food Walking Tour With A Local Guide
Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary landscape, tracing the influence of immigrants on the city's gastronomy. Indulge in the iconic Chicago deep-dish pizza, renowned for its thick crust and flavorful fillings, followed by a visit to a historic eatery for the famed dipped Italian beef sandwich, a local favorite. Amidst culinary delights, marvel at architectural marvels like Cloud Gate and the Chicago Cultural Center, adding depth to your exploration. As the tour unfolds, anticipate a tantalizing surprise: a secret dish, revealed only on the day of your adventure, promising an unexpected culinary delight. This immersive experience offers not only a feast for the palate but also insights into Chicago's rich culinary heritage and architectural splendor.
Duration: 3 hours
- Free cancellation
- Private tour
Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer
Book your Private Round-Trip Transfer from Chicago Midway Airport (MDW) to Chicago or address and return.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers
Duration: 50 min
- Free cancellation
- Private tour
Save 5%
Departure Private Transfer: Chicago to O'Hare Airport ORD in Luxury Car
Your safety is our crew’s biggest priority. Before your journey even begins, your chauffeur completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-trained drivers will greet you with a name sign in the reception of the hotel, will offer to assist with luggage and guide you to your vehicle. Your driver will open and close the door for you, and for your safety, guests are only permitted to ride in the back seat. We’re here to ensure you arrive at your destination feeling healthy, happy, and ready to take your flight.
Duration: 30 min
- Free cancellation
- Private tour
Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets
Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time.
Highlights:
• Discover downtown Chicago on foot with a 5-Star Private Guide leading the way
• Cruise Lake Michigan with included tickets and audio commentary onboard
• See breathtaking skyline views and snap iconic photos from the water
• Learn the city’s best-kept secrets through fascinating stories and history
• Get tailored recommendations on top spots to eat, visit, and explore next
Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!
Duration: 3 hours
- Free cancellation
- Private tour
Chicago Pope Leo XIV's Roots Tour
Discover the unique journey of Pope Leo XIV through Chicago on this interactive bus tour. Visit his childhood home and childhood church in the suburb of Dolton on this one of a kind experience. This tour not only showcases the Pope's life but also intertwines the vibrant culture of Chicago, making it a must for both visitors and locals. Enjoy exclusive insights from knowledgeable guides while engaging with the city's rich history and faith.
- Guided bus tour through Chicago’s historical sites related to Pope Leo XIV
- Pickup at Holy Name Cathedral in the heart of the city
Duration: 2 hr 30 min
- Free cancellation
Chicago Riverwalk Architecture Walking Tour
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
Duration: 1 hr 30 min
- Free cancellation
Save 10%
Chicago Gangsters and Ghosts Late Night Halloween Special
Uncover the chilling history of Chicago's gangsters and ghosts on this thrilling late-night Halloween walking tour. Delve into the dark secrets of the South Loop, once a vice district, as your historian guide shares captivating tales of Al Capone and the city’s infamous past. Explore haunted locations like the Palmer House and the Chicago Theatre, and hear eerie stories of spirits that linger in Death Alley and along the Chicago Riverwalk. This tour culminates at the Congress Hotel, renowned for its ghostly sightings, making it the perfect way to experience Chicago's haunted history at midnight.
- Late-night Halloween walking tour through Chicago's South Loop, ending at midnight.
- Hear true stories about notorious gangsters like Al Capone
- Visit haunted spots including the Chicago Theatre and Palmer House
- End your tour at the Congress Hotel, one of Illinois' most haunted locations
Duration: 2 hours
- Free cancellation
![Downtown Chicago City Tour in a Super Car [30 Minute Experience]](https://media-cdn.tripadvisor.com/media/attractions-splice-spp-400x400/r/33/f9/b4/9e/caption.jpg)
Downtown Chicago City Tour in a Super Car [30 Minute Experience]
Turn heads and take in the views with your Premier Chicago Tour Experience!
Your journey begins in the passenger seat of an automotive masterpiece. Tour downtown Chicago in an Exotic Sports Car where you'll discover the luxury boutiques of the Magnificent Mile, and enjoy breathtaking waterfront views on Lake Shore Drive. After your scenic tour, enjoy 10 minutes of dedicated photo-op time at the departure point located at the Heart of Downtown Chicago. Whether it’s for social media or a personal keepsake, you’ll have plenty of time to pose with these mechanical works of art against the backdrop of the Windy City before your next adventure begins.
More info
THE VEHICLES CONSIST OF EXOTIC SPORTS CARS FROM MAKES SUCH AS LAMBORGHINI, FERRARI, MCLAREN, ASTON MARTIN & MORE!
Group passenger vehicles consist of Vehicles from make such as Lamborghini, Aston Martin, Rolls-Royce, Bentley & MORE.
Duration: 30 min
- Private tour
Kite Coloring Workshop in Chicago
Discover a cherished Chinese tradition through a fun and creative Kite Coloring Workshop in Chicago's Chinatown. Learn about the fascinating history of kites, which were first invented in ancient China, and hear the cultural stories behind this centuries-old art form. Then, let your creativity shine as you design and color your own blank silk kite under the guidance of experienced instructors. Once your masterpiece is complete, you'll take it home as a unique keepsake of your cultural experience. This hands-on activity is suitable for all ages and offers an engaging way to connect with Chinese heritage through art and storytelling.
- Learn the history and cultural significance of traditional Chinese kites.
- Design and color your own silk kite to create a one-of-a-kind souvenir.
- Enjoy a hands-on cultural activity suitable for participants of all ages.
- Take your finished kite home as a memorable keepsake
Duration: 45 min
- Free cancellation
Save 6%
Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business Car
Your safety is our crew’s biggest priority. Before your journey even begins, your driver completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-trained drivers will greet you with a name sign in the arrivals terminal of the airport, will offer to assist with luggage and guide you to your vehicle. Your driver will open and close the door for you, and for your safety, guests are only permitted to ride in the back seat. We’re here to ensure you arrive at your destination feeling healthy, happy, and ready to take on the day.
Duration: 30 min
- Free cancellation
- Private tour
Meet and Greet Private Sedan Transfer from ORD to Downtown Chicago
Reliable and luxury airport transfers
Best and most professional Chauffeurs in the industry
Up-to-date luxury vehicles
High quality of service
Smart rates
Duration: 30 min – 1 hr 30 min
- Free cancellation
- Private tour
Podcast Tour Chicago The Promised Land and the Black Metropolis
Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migration—a time when millions of African Americans fled the Jim Crow South to build a self-sustaining 'Black Metropolis'. From the birthplace of gospel music to the headquarters of a newspaper that changed the nation, discover the triumphs of entrepreneurship, the brilliance of cultural innovation, and the unyielding spirit of a community that shaped modern America.
A 3.9 km self-guided tour with 7 stops over 121 min
Ideal for travelers interested in Identity, Migration & Globalization and History & Memory
Immersively told in a podcast style by experts and locals
Matching audio content, AI guide and navigation through the app
Duration: 2 hr 1 min
- Free cancellation
Save 6%
Chicago Airport Transfer: Chicago to O'Hare Airport ORD in Business Car
Your safety is our crew’s biggest priority. Before your journey even begins, your chauffeur completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-trained drivers will greet you with a name sign in the reception of the hotel, will offer to assist with luggage and guide you to your vehicle. Your driver will open and close the door for you, and for your safety, guests are only permitted to ride in the back seat. We’re here to ensure you arrive at your destination feeling healthy, happy, and ready to take your flight.
Duration: 30 min
- Free cancellation
- Private tour
Private Sedan Transfer from Chicago Downtown to O`Hare airport
Reliable and luxury airport transfers
Best and most professional Chauffeurs in the industry
Up-to-date luxury vehicles
High quality of service
Smart rates
Duration: 30 min – 1 hr 30 min
- Free cancellation
- Private tour
Private Transfer by Luxury Car to ORD Airport
Free purified water and free soda on board. Passengers will have the option to play their music on board.
Duration: 2 hours
- Private tour
Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt
Celebrate the magic of the season this year with Holly Jolly Hunt. Holly Jolly Hunt is an app based scavenger hunt that you can play anywhere of your choosing. Explore the city and look for holiday related items, both traditional and not so traditional. Take a photo through the app to score points for your scavenger hunt team. Perform fun, holiday challenges that will bring laughter to your team. See your score on the leaderboard compared to other teams from all over. Holly Jolly Hunt is guaranteed to provide lasting holiday memories. Whether you play with friends, family, or even co-workers, Holly Jolly will put a smile on your face for the rest of the year!
Duration: 1 hour
- Free cancellation
- Private tour
2 Hour Chatham, Chicago Tour
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
Duration: 2 hours
- Likely to sell out
- Free cancellation
A Spectacular Scavenger Hunts Chicago Adventure
Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered. Challenge yourself with trivia, tackle brain-teasing puzzles, and embark on an epic journey of exploration!
Whether you’re collaborating with your crew or turning up the competition, Let’s Roam Adventure Hunts guarantee a blast for all. Perfect for any occasion—whether it’s a spontaneous outing, a wild bachelorette bash, a festive birthday celebration, or a team-building extravaganza.
Each player gets to dive into an interactive role, ensuring every challenge is as thrilling and unique as the next. So, gather your squad, choose your adventure, and let the good times roll!
With Let’s Roam, every outing becomes a treasure trove of memories and excitement. Are you ready to conquer the city and create unforgettable experiences? Let’s Roam and make every day an adventure!
Duration: 1 hr 30 min
- Free cancellation
- Private tour
Meet and Greet Private SUV Transfer from MDW to Downtown Chicago
Reliable and luxury airport transfers
Best and most professional Chauffeurs in the industry
Up-to-date luxury vehicles
High quality of service
Smart rates
Duration: 30 min – 1 hr 30 min
- Free cancellation
- Private tour
Chicago-Milwaukee Small Group Tour
Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!
Duration: 6–7 hours
- Free cancellation
Private SUV Transfer Between O'Hare airport & Downtown Milwaukee WI
Reliable and luxury airport transfers
Best and most professional Chauffeurs in the industry
Up-to-date luxury vehicles
High quality of service
Smart rates
Duration: 1 hr 15 min – 1 hr 40 min
- Free cancellation
- Private tour
Chicago Gangsters and Ghosts Walking Tour
We are the original, top-rated Gangsters and Ghosts tour! As a private tour, hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your private historian guide, uncovering the many mysteries hidden behind every turn.
Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies and bootleggers.
Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business".
Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.
Duration: 2 hours
- Free cancellation
- Private tour
Save 20%
Self-Guided Podcast Tour Chicago: Michael Jordan's West Side
Step into the grit and glory of Michael Jordan’s 1990s Chicago Bulls dynasty. We trace the physical collision between global basketball myth and the reality of the Near West Side. From high school talent pipelines and pickup courts to working-class fan taverns, the vanished Chicago Stadium, and the redeveloped housing projects across Lake Street, this walk explores how an industrial city rebranded itself into an international sports capital—and what that transformation meant for the neighborhood living in the arena's shadow.
- A 3.9 km self-guided tour with 8 stops over 139 min
- Ideal for travelers interested in Pop Culture & Media Landscapes and History & Memory
- Immersively told in a podcast style by experts and locals
- Matching audio content, AI guide and navigation through the app
Duration: 2 hr 19 min
- Free cancellation