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 Private Lakefront Sunset and Skyline Photo Tour
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.
Duration: 2 hours
- Free cancellation
- Private tour
Curbside SUV 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
Chinatown History and Culture Tour
Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001.
Discover the history, culture, and hidden stories of Chicago’s Chinatown on a guided walking tour through one of the city’s most vibrant neighborhoods. Starting at Chinatown Library, you'll visit iconic landmarks, including Chinatown Square, Chinatown Mural, Ping Tom Memorial Park, the Chinatown Gate, Nine Dragon Wall, Pui Tak Center, Chinese Buddhist Temple, St. Therese Chinese Catholic Church, and more. Along the way, you'll learn about Chinese heritage, local traditions, and the community’s lasting impact on Chicago before ending at the historical old Chinatown.
- Explore Chicago Chinatown with a knowledgeable guide.
- Learn about Chinese culture, history, and traditions.
- Admire public art and the Chinatown Mural
- Perfect for first-time visitors and returning guests alike
Duration: 1 hr 30 min
- Free cancellation
2 Hour Englewood, Chicago Tour
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
Duration: 2 hours
- Likely to sell out
- Free cancellation
Chicago Bears Football Game at Soldier Field
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!
Duration: 4 hours
Adventurous Scavenger Hunt in Chicago by Crazy Dash
With Crazy Dash, you'll use an app to explore Chicago in this exciting scavenger hunt! Use an app to find things around the city in any order you want, take photos, and collect points. At the end, take a look at the rankings to see your score compared to others across the country. All scavenger hunts have a live remote host that will help via chat. Crazy Dash is our most easy-going scavenger hunt. Come join us in Chicago today!
Duration: 2 hours
- Free cancellation
- Private tour
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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
Chicago Local Fashion Designers Shopping Tour with a Stylist
Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes.
Learn more about the art of styling your body features and take a figurative soft tour outside your comfort zone as your stylist pulls pieces for you to explore and try. Think of it as a mini style consultation followed by recommendations and a hands-on practice session during the shopping tour where you can ask any fashion and style-related questions.
Throughout your shopping circuit and neighborhood's discovery, listen to fashion stories as told by your fashion savvy guide, and get a unique insight into the industry.
Prior to your shopping tour, you will be sent a little shopping form to help personalize your experience. And following your fashion escapade, you will be sent a personal style summary of recommendations received by your stylist as well as some tour souvenir photos.
Duration: 3 hours
Private History and Architecture of Chicago Loop Walking Tour
This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy to customize the tour itinerary and content for your group.
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.
Duration: 2 hr 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
Dark Tales of Bucktown: A Self-Guided Chicago Tour
Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the neighborhood's murders, hauntings, and disappearances, encountering a real-life fugitive, the ghost of a pub owner who still tends bar, and a winged creature with red eyes spotted across Chicago.
Starting at the former Lincoln Tavern, where a 1980 robbery ended in multiple murders, you'll pass the spot where a 12-year-old boy was killed by a train in 1902. You will see where residents still report signs of his presence, and walk by the only Opus Dei-operated church in the country.
The tour ends at Club Lucky, where three bullet holes still visible in the bar mark the spot where a Polish immigrant named Walter met his unfortunate end in January 1967. Sweet dreams.
Duration: 40 min – 1 hr 20 min
- 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
Chicago Suburbs Movie Sites Private Tour
Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s Day Off and Home Alone to modern hits like The Dark Knight. Led by a local actor guide, explore iconic homes, schools, and streets while hearing behind-the-scenes stories and fun film trivia. Perfect for movie lovers and anyone wanting a fresh, cinematic look at the Chicago suburbs.
Duration: 2–3 hours
- Private tour
Chicago to Chicago Airport (MDW) - Departure Private Transfer
Book your private departure transfer from Chicago to Chicago Midway Airport (MDW).
Your driver will be waiting for you at the scheduled time, and you can travel comfortably to your destination.
Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.
Duration: 30 min
- Free cancellation
- Private tour
Luxury Limousine Transfers in Chicago
Elevate your travel experience in Chicago with luxurious limousine transfers that redefine comfort and sophistication. Whether it’s a corporate event, wedding, or a night out, each ride offers plush interiors and exceptional service from professionally trained chauffeurs. Enjoy complimentary bottled water as you glide through the city in style, taking in the vibrant urban landscape. With options ranging from sedans to spacious SUVs, every detail is catered to ensure your journey is seamless and memorable.
- Premium vehicles including Cadillac and Mercedes-Benz options
- Professional chauffeurs familiar with the best routes
- 24/7 service to accommodate your schedule
- Group bookings available for larger parties or events
Duration: 1 hour
- Free cancellation
- Private tour
Wheelchair Accessible Airport Transfer Chicago to O’Hare, Midway
Travel in Comfort & Accessibility with Chicago’s Premier Private WAV Service.
Your professional, fully licensed driver will meet you curbside at O’Hare (ORD) or Midway (MDW) and assist with boarding into our wheelchair-accessible Toyota Sienna WAV.
✓ Private, insured service with $350,000+ commercial coverage
✓ Fully wheelchair-accessible vehicles with secure restraints
✓ Safe, quiet ride in a clean, premium vehicle
✓ 16 years of trusted transportation service in Chicago
✓ 5× Certificate of Excellence award-winner on Viator
- Free cancellation
- Private tour
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
Small Group Walking Tour of Chicago The Loop
Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through the heart of the city, you'll uncover fascinating stories, admire world-renowned architecture, and learn about the pivotal events that helped shape Chicago into one of the world's most influential destinations.
With a small group, you'll enjoy a relaxed and interactive experience, giving you plenty of opportunities to ask questions and connect with your guide. Along the way, you'll receive insider tips on the best places to eat, drink, and explore, helping you experience Chicago like a local long after the tour ends.
Whether you're visiting for the first time or returning to discover more, this tour offers an engaging introduction to Chicago's history, culture, and architectural heritage.
Duration: 2 hr 30 min
- Free cancellation
Prohibition Chicago: Myth vs. Reality Walking Tour
More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate.
On this tour, you’ll hear how the culture in turn-of-the-century Chicago helped bring about the 18th Amendment through stories of notorious vice districts along the Chicago River and the South Loop. We'll talk about the rise of Al Capone during the infamous “Beer Wars,” culminating in the St. Valentine’s Day Massacre. Along the way, we’ll talk about how the city played a role in the popular and artistic growth of jazz, and how Chicago during the Roaring Twenties has been depicted on screen, in blockbusters such as "The Untouchables" and "Chicago."
Please be advised that this tour contains stories of murder and sex work. Although children are welcome on this tour, parents should use their discretion in determining whether it is suitable for those under 15.
Duration: 2 hours
- Free cancellation
Private Transfer from Chicago (ORD) Airport to Chicago City
Take the worry out of your arrival to Chicago (ORD) Airport and pre-book a private transfer to suit your group size (up to 14 people). Avoid the long lines for taxis on arrival, and travel in the comfort of a Premium car or minivan.
Duration: 35 min
- Free cancellation
- Private tour
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
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Arrival Transfer: O'Hare Airport ORD to Chicago by Luxury SUV
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
Curbside Sedan Transfer from O`Hare Airport 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