BYOB Chicago River Guided History Tour
Discover the fascinating history of Chicago from a whole new perspective — on the water! This 120-minute Guided History Tour along the Chicago River brings the city’s past to life through captivating stories, iconic landmarks, and little-known facts that shaped the Windy City into what it is today.
• Chicago’s transformation from swamp land to industrial hub to the modern metropolis it is today
• The dramatic story of the Great Chicago Fire of 1871 and how the city rebuilt stronger than ever
• Tales of Chicago’s most infamous gangsters and Prohibition-era legends
• The groundbreaking 1893 World’s Fair and the inventions it introduced to the world
• The incredible reversal of the Chicago River — its purpose and lasting impact on the city’s future
Step aboard and experience how history, architecture, and innovation flow together on this unforgettable journey through Chicago’s past and present.
Self-Guided Chicago Loop Tour Explore the City at Your Own Pace
Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown.
This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline.
Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit.
The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll.
— Self-guided exploration of Chicago’s historic Loop area
— Learn about the city’s architectural innovations and history
— Visit iconic landmarks like the Art Institute and Millennium Park
— Perfect for first-time visitors or seasoned Chicagoans alike
360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour
Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on open-top buses while enjoying engaging audio commentary that reveals the rich history and culture of the Windy City. This tour includes admission to the stunning 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center, offering breathtaking panoramic views of Lake Michigan and the city skyline.
- Unlimited hop-on hop-off access for 48 hours across top Chicago attractions
- Audio commentary in multiple languages covers local history and culture
- Admission to the 360 CHICAGO Observation Deck for breathtaking views
- Perfect for first-time visitors, families, and those seeking flexible exploration
Time selected at booking is for 360 CHICAGO admission. Big Bus Hop-on Hop-off Tour available anytime during operating hours.
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hancock Tower. Your guide is a local who has plenty of tales about Chicago life together with an in-depth knowledge of its character.
As you journey down the Magnificent Mile, you will learn how Chicago has earned each of its nicknames, including the City of Broad Shoulders, the Second City, and of course, the Windy City. Lastly, your guide will escort you to the Hancock Tower to bid on your adieus.
You will then travel to the top of the Hancock Tower’s Observation Deck, where you can enjoy 360-degree views of the entire city at your own leisure.
Private Wicker Park and Bucktown Walking Tour
This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a whole different side of the city.
The tour has 2 options:
Wicker Park and Bucktown - faster pace, 2.5 miles of walking.
Wicker Park only - slower pace, 1.5 miles of walking
Private SUV Transfer from Chicago Downtown to Midway 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
Private Holiday City Tour
Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjoy all the Holiday sites the city is known for including, Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. This experience is the only way to see Chicago during the holidays!
Luxury SUV O'Hare/Midway Airport (Curbside) Chicago One Way
THE PREMIUM SUV OFFERS SEATING FOR 6 PASSENGERS, WITH LUGGAGE CAPACITY FOR 3 CHECKED-IN BAGS AND 2 CARRY-ON ITEMS.
Luxurious Fleet: Our fleet consists of top-of-the-line luxury vehicles, meticulously maintained to provide the utmost comfort and style during your journey. Whether you're traveling solo, with a group, or for a special occasion, we have the perfect vehicle to suit your needs.
Professional Drivers: Our drivers are not only highly skilled behind the wheel but also epitomize professionalism and courtesy. They prioritize your safety and satisfaction, ensuring a smooth and enjoyable ride from pick-up to drop-off.
Friday Night Pizza Crawl - River North, Chicago
Based on the book, "Pizza City USA," this tour features three different styles of pizza in less than 3 hours. You'll meet some of the pizza makers behind the pies, learn about Chicago pizza history (and the greater city at large) plus discover a pair of places few locals even know about. You'll be sampling deep-dish, artisan and Neapolitan-style pizzas on this tour. (Masks required)
Chicago Air and Water Show VIP Cruise or Skydeck Experience
Chicago Air and Water Show 2025
Great for friends & family!
PLEASE READ CAREFULLY
Experience Chicago’s Air & Water Show from the Best Seat on the Lake!
10AM SAIL: Our first sail will depart at 10am sharp. Our first event will be the Air and Water Show, and will showcase a wide variety of aircraft, and demonstrations, which will be watched from the *best location, as determined by the Captain. We will return to our dock by 12:30pm.
1PM SAIL: This sail will depart at 1PM sharp. As this is our second sail for the Air and Water Show, this sail will also showcase a wide variety of aircraft, and demonstrations, INCLUDING THE MAIN EVENT. This will be watched from the *best location, as determined by the Captain. We will return to our dock around 3:30pm, but this may be delayed, if the show is delayed, to ensure your viewing of the main event, if it happens.
Chicago 6-Hour City Tour by Sedan
Luxury vehicles
Professional chauffeurs
Updated fleet
Licensed chauffeurs
Knowledge about navigating in the city
Private Photography Session with Local Photographer in Chicago
Flytographer Private Vacation Photo Shoot
Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Chicago, including where to eat & what to see from your vacation photographer. Return from your trip with beautiful, high-quality vacation photos — the best souvenir ever.
We specialize in:
- honeymoons
- family trips
- engagements
- anniversaries
- romantic getaways
- multi-generational trips
- babymoons
- solo travellers
- and just because!
With over 10,000 5-star reviews, Flytographer is the global leader in vacation photography and has captured over 3 million memories for travellers across six continents. We’ve been featured across A-list media, including Conde Nast Traveler, Oprah, Forbes, Travel + Leisure, New York Times, BRIDES, Martha Stewart Weddings, InStyle Magazine, Elle, Buzzfeed, Refinery29, Huffington Post, & many more.
Custom Chicago Walking Tours
We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high school students, to tavern tours tracing Chicago’s beer history, to local neighborhood food tours, every tour is crafted to be engaging, flavorful, and unforgettable.
Gangs and Mobsters Crime Tour at Chicago
Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, where the echoes of a century of Mob activity intertwine with the modern cityscape. Traverse the iconic Michigan Avenue, once a hub of illicit operations masterminded by the infamous Al Capone, and uncover the hidden secrets of the past that now lie beneath the surface of changing demographics and contemporary establishments. Brace yourself for chilling tales of mob hits and ongoing underworld dealings, as you unravel a dark and compelling narrative that still resonates through the streets today.
6-Hour Private SUV Transportation Service in Chicago
Luxury vehicles
Professional chauffeurs
Updated fleet
Licensed chauffeurs
Knowledge about navigating in the city
Original Chicago Prohibition Bus Tour
Our Original Bus Tour is a deep dive into Chicago's most notorious era. Taking you to neighborhood gems you may not find on your own, grab a drink and enjoy the history of the men, women and locations (famous and infamous) that helped shape Chicago as we know it today.
Adventurous Scavenger Hunt in Chicago by Zombie Scavengers
This experience is unique for its unmatched flexibility and strong emphasis on group interaction. It’s not bound to a fixed schedule or route, allowing groups to start, strategize, and explore at their own pace. The core difference is the immersive, lighthearted zombie theme that dictates the tasks—you're scavenging for supplies and completing silly challenges to prove your survival mettle. It’s perfect for team-building or family fun because it's priced per team (up to 10 people), includes the guidance of a remote, chat-based host, and culminates in the unique bragging rights of checking your national rank on the app's leaderboard.
Curbside Sedan Transportation from O'Hare or Midway Airport to Downtown Chicago
Safety is our main focus! All our chauffeurs are licensed and our vehicles are regularly maintained. You will feel safe with us!
O'hare Airport Taxi (ORD) To Chicago Downtown
At Ohare Airport Taxi LLC, we specialize exclusively in private transportation to and from O’Hare Airport, located in Chicago, Illinois. Our service is designed for passengers who value punctuality, comfort, and professionalism.
We operate a modern fleet of commercially licensed and insured vehicles, all well maintained, spotless, and equipped for a safe and smooth ride. We are not a ride sharing. We are a fully licensed professional limo style service, with all the necessary permits to legally pick you up at O’Hare Airport.
Our full time, experienced drivers know Chicago and the airport inside and out. They track flights in real time to ensure your pickup is timely and stress free, even in case of delays or early arrivals.
Booking your Taxi to O’Hare Airport has never been easier. Whether you're traveling for business or leisure, Ohare Airport Taxi LLC is the most reliable and professional choice for airport transportation in Chicago.
Private City Tour 6-10ppl
PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago. Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more. The tour will be interactive and entertaining, covering history, architecture and culture. We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.
Chicago Scavenger Hunt & Highlights Self-Guided Walking Tour
The Best Way to Discover Chicago: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a photo at Maggie Daley Park or a visit to the Shedd Aquarium and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups.
The "Complete City" Package - Everything you need in one app:
Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way.
Learn the history/legends of each site.
Insider Tips: Access hand-picked local restaurant and shop recommendations.
What you will visit: Navy Pier, Franklin Delano Roosevelt Bridge, Maggie Daley Park, Millennium Park, The Art Institute of Chicago, Clarence F. Buckingham Memorial Fountain, Queen’s Landing, Field Museum, Shedd Aquarium, and Adler Planetarium.
Chicago and All MidWest Self Guided AI Audio Tours for 7 Days
With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mile—or dive deep into 1920s mobster hangouts and hidden Prairie Style masterpieces. Ask about literally anything that catches your eye—from a Gilded Age historic district to a secret jazz club or a towering steel-and-glass skyscraper. The Windy City's deepest secrets are entirely yours to uncover.
Point & Discover: Snap a photo of any monument or museum masterpiece to instantly receive a captivating and accurate story. It’s like having a historian in your pocket!
Ultimate Freedom: Navigate seamlessly with interactive map-based audio tours. Your schedule, your pace, your rules.
Choose Your Vibe: Select a narrator persona that matches your style—from a deep-diving scholar to a fun companion for the kids.
Get Started: 7 Days of Premium Access available instantly for iPhone and Android.