Top Chicago How to Get Around in 2026

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginning near the iconic Palmolive Building, this guided experience takes you through the city’s Gold Coast and beyond, uncovering the eerie aftermath of the Great Chicago Fire and the restless spirits it may have left behind. Along the way, you’ll visit a curated mix of historic sites and local bars, blending chilling storytelling with time to grab a drink and soak in the atmosphere. Adults 21+ only, must have valid I.D.

If it’s your first time in Chicago or you just have limited time, make the most of a day in the Windy City on a private driving tour. Instead of navigating public transit or waiting for ride shares, relax as a dedicated driver takes you to all the major attractions of downtown and beyond, including Navy Pier, Michigan Avenue, Wrigley Field, Millennium Park, and Museum Campus. Plus, get local insight into Chicago along the way.

Discover Chicago in a fun new way—and combine your sightseeing with a lively scavenger hunt—on this 2-in-1 excursion. With your smartphone in hand, set off at a time that works best for you on this self-led tour. Prompted by the game, explore the Windy City's vibrant Loop neighborhood. Spot historic buildings, famous streets, and other local landmarks along the way, all while your party solves clues and challenges.

Don’t leave Chicago without taking home professional digital and polaroid shots of your visit. Starting from the iconic Millennium Park, your photographer guide takes you to some of the city’s most photogenic landmarks to take photos of you that really pop—once it’s over, you can take home about 100 digital photos and five polaroid shots.

On most tours of Chicago, you only see a small selection of the city’s highlights, but you can customize this flexible-duration private tour to suit your schedule and tastes. Choose to discover hidden gems that most tourists miss, snap photos of landmarks like the Willis Tower, explore the Windy City’s shopping scene, and much more.

The Art Institute of Chicago is home to over 300,000 works of art by local and international artists. With so much to explore, it’s easy to get overwhelmed by all of the options during a visit. Sit back and let an expert guide handle the planning as they take you through the museum’s major pieces. Learn about the history and context behind each piece in this culturally enriching experience.

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the ride while exploring Chicago's iconic filming locations. Tour Highlights: - Visit the exterior of Gallagher House (Private Residence) - Visit the exterior of Sheila's House (Private Residence) - Visit the exterior of Kelvin & Veronica's House (Private Residence) - Explore Millennium Park and take a photo in front of the famous "Bean" Sculpture, a popular Chicago Landmark. - Explore the Chicago Cultural Center renowned for its stunning architecture, including the world's largest Tiffany stained-glass dome. This tour offers a unique blend of Shameless fandom and Chicago exploration, while prioritizing respect for private residences and local communities.

Discover the hidden gems of Lincoln Park on a private, open-air pedicab ride guided by a local storyteller. Relax as you explore lush gardens, the iconic lily pond, lakefront views, and landmark architecture— all without the effort of walking or the crowds of bus tours. Your route and pace are fully customizable, with plenty of photo stops and personal stories that bring Chicago’s past to life. Perfect for families, visitors with mobility needs, photography lovers, or anyone seeking a breezy, memorable Chicago adventure.

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby. Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, The Dark Knight, The Bear, and more. See the theater from Public Enemies, Harold Washington Library from Ocean’s Eleven, the Chicago Board of Trade and Calder’s Flamingo from Ferris Bueller, iconic Blues Brothers spots, and Bruce Wayne’s penthouse and Harvey Dent’s office from The Dark Knight. Perfect for film buffs and Chicago enthusiasts alike.

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks and hidden streets, capturing the city’s character from golden hour through to its dazzling night lights. As skyscrapers glow and trains blur past, your professional guide helps you master techniques like composition, long exposure, and low-light shooting. Designed around your skill level, this private tour ensures one-on-one coaching, creative development, and unique photo opportunities. It’s more than sightseeing—it’s a hands-on journey through Chicago’s streets after dark, where every corner becomes a chance to create striking images. Creative composition, using lines, repetition, camera angles Training your eye: finding subjects, lighting, composition Taking control of your camera: f-stop, shutter speed, ISO and focusing Reviewing your photography

Take a deep dive into the world of "Chicago Fire" and learn more about what it’s like behind the scenes of your favorite show on this private tour. Visit filming locations such as the exterior of Firehouse 51 and Molly's Bar, and popular tourist attractions, including the Bean at Millennium Park and the Chicago Cultural Center. Plus, enjoy handy hotel pickup if your accommodation is within five miles of downtown Chicago.

Chicago is famous for its architecture, but it takes an expert to decode its various styles. See all that the Windy City has to offer—from Gothic Revival, Art Deco, Modernist, and more—on this guided walking tour. Enjoy stunning lakefront views from Millennium Park, then catch century-old landmarks along the Magnificent Mile.

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who shares local stories, historical insights, and highlights the architecture and communities that shape the city’s unique character. Begin in the Gold Coast Historic District with its elegant mansions and tree-lined streets, then explore Lincoln Park with its scenic paths, gardens, and historic zoo. Visit Wrigley Field to experience Chicago’s sports culture, followed by Hyde Park and the University of Chicago, known for its stunning architecture and intellectual heritage. Conclude in Chinatown, a lively cultural district with colorful streets, markets, and traditional restaurants. With a flexible, door-to-door itinerary, this private tour offers a relaxed, immersive way to experience Chicago’s history, culture, and diverse neighborhoods.

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant neighborhoods with personalized attention and insider knowledge. Enjoy a hassle-free day with transportation, tickets, and lunch included. Explore Millennium Park, Navy Pier, and more, with plenty of photo opportunities and fascinating stories. Book now for an unforgettable Chicago adventure!

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

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. We are true fans of Chicago, The Bear and good food which is why we start our tour at the world famous Pequod's pizza where a hot pie will be ready waiting for us to pickup and try. Enjoy this in the pedicab as we begin our leisurely ride through the city getting an open air view of some of Chicago's cutest neighborhoods. Next up we go to Margies Candies for a Banana Split before embarking on a ride all the way from the west side to River North, crossing the Chicago River and getting some photos at the iconic LaSalle Flowers. End your epic Chicago adventure at Mr. Beef or Kasama! Your tour vehicle will be a decorated 6 seat pedicab driven by one of our knowledgeable tour guides. Comfortable for up to 4-5 adults, 6 if kids/teenagers are in the mix. Look at the photos of the cab and feel free to reach out with any questions.

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking parks, the famous Cloud Gate (The Bean), world-class museums, and renowned stadiums. Whether you’re attending a concert, exploring historic sites, or enjoying a day at the park, our professional chauffeur service ensures a seamless and luxurious journey. With our SUV tours, you'll have the flexibility to explore at your own pace. Visit top attractions like Millennium Park, the Art Institute of Chicago, and the Field Museum. Enjoy a thrilling game at Wrigley Field or United Center or take in a concert at Allstate Arena. Our chauffeur will drop you off and pick you up at each location, providing you with the utmost convenience. Book your tour today and let us take care of the details. Travel in comfort and make the most of your time in Chicagoland with our premium SUV tour service.

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!

Explore the Chicago River in a unique way with this 120-minute Guided Ghost Tour. Learn about the city's haunted history, including the Great Chicago Fire and the Eastland Disaster. You are welcome to bring your own beverages and food/snacks to fully enjoy your time on the water. Departing from the Chicago Riverwalk, this is a fun and engaging way to experience the spooky side of the city. This tour is typically smaller allowing for you to interact with the tour guide! Ask all the questions, we are ready! - 120-minute ghost tour on the Chicago River for up to 18 passengers - Fun bring-your-own beverage/snacks experience with a u-shaped bar and coolers - Learn about Chicago's haunted history and significant events - Departures from the Chicago Riverwalk—15-minute early arrival required to allow time for check in and depart on time.

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.

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.

Shoreline water taxis are the fast and fun way to get to Chicago’s top attractions. Our water taxis aren’t tours, but they are a great way to get around town. Offering multiple docks conveniently located near major attractions including Navy Pier, the Willis (Sears) Tower, Michigan Avenue, Museum Campus, and Union Station.

This self-guided walking tour is perfect for last-minute travelers who love chocolate! Travelers will use the eATLAS app for directions on where to go, and what to do--map included. You can start and pause the Adventure whenever it is convenient for you. Chicago was once the “Candy Capital of the World,” and chocolate has been a rich, decadent part of the city’s culinary history longer than deep-dish pizza and Italian beef. Milton Hershey even learned how to make chocolate in Chicago at the 1893 World’s Fair. Some of the world’s most beloved chocolate treats, including Tootsie Rolls, Baby Ruth, Butterfinger, Snickers, 3 Musketeers and Milky Way, were invented or are manufactured here. There are 8 delicious Loop and River North stops on our tour/scavenger hunt. Simply read the clues and follow the directions to guess the answers. Hints are provided if you need help. You won’t be required to buy anything, but if you need a quick pick-me-up, what’s better than chocolate?