Top Chicago How to Get Around in 2026

Head to one of Chicago’s top neighborhoods for food lovers—and try donuts from four of the Windy City’s top specialty bakeries—on this indulgent walking tour. Meet your guide at the Chicago French Market in the morning, and come hungry: you’ll enjoy four different donuts, each representing different culinary styles and traditions. As you go, wander the West Loop and Restaurant Row, and learn more about Chicago’s dining scene.

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.

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at every stop, while taking in the captivating sights of the Windy City. Whether you're a resident or visitor, this exclusive ride offers a fresh perspective of Chicago's vibrant energy and charm. Don’t miss the chance to explore the city like never before—reserve your adventure and drive through Chicago’s heart in true sophistication. All tour vehicles are subject to availability During This Ride You May See Views Of The Following Land Marks: Little Italy Willis Tower Harold Washington Library The Chicago Theatre Millennium Park Grant Park Buckingham Fountain Magnificent Mile Gold Coast Museum of Science & Industry Lake Michigan And much more! We cannot guarantee that all sites on this list will be seen in your tour.

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin an immersive journey through the galleries. Together, we'll explore the museum's most celebrated highlights, featuring masterpieces by Monet, Picasso, Van Gogh, Dalí, Warhol, Hopper, and more. I'll share fascinating stories that bring the art and its creators to life, revealing the hidden meanings and personal histories behind. Along the way, I'll capture beautiful, candid photographs at the best photo spots. Using your phone or my iPhone 14 Pro, I'll guide you with simple posing tips and angles to ensure you receive stunning, professional-quality images perfect for memories or social media. Anyone looking for more than just a museum visit, you'll leave with gallery-worthy images plus knowledge that transforms how you experience art—an unforgettable blend of photography, storytelling, & culture. Looking forward to hosting you!

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and construction history. Get a unique chance to combine touring by foot and by L train, and see the city’s most iconic landmarks like The Rookery Building, Chicago Cultural Center, First Arts Building, and more 19th and early 20th-century masterpieces. Be ready to see the City by the Lake from a new perspective and get to know it even closer as you stroll down its streets and travel by train. Enjoy the small-group experience and don’t miss a thing as you travel Discover the downtown and historical building together with your local knowledgeable guide Marvel at architectural landmarks of the City by the Lake and get to know the stories behind them Combine a walking tour with a train to see more landmarks and iconic sights on one tour.

Chicago is well known for its architecture and many visitors admire the buildings on a cruise along the Chicago River. Take your river cruise to the next level aboard a floating tiki bar that allows you to take in all the sights with a drink in hand. Your captain also enhances the atmosphere with island tunes as you enjoy your leisurely sail.

Dive into Chicago’s Magnificent Mile on an interactive scavenger hunt, perfect for families, friends, or team building! Guided by clues on your phone, you’ll solve puzzles, unlock local legends, and discover iconic sites like the Old Water Tower, Tribune Tower, and bustling Riverwalk—plus hidden gems along the way. Go at your own pace, compete for fun, and see the best of Chicago’s lively downtown in a whole new way. Teams of up to six welcome; no local knowledge required—just curiosity and comfy shoes.

Step inside a unique and fascinating journey through Chicago’s premier indoor mushroom farm, as seen on FX/Hulu’s acclaimed series "The Bear," where our mushrooms were featured by the show’s chefs. During this tour, you'll discover how exotic culinary mushrooms are cultivated for Chicago’s top Michelin-starred restaurants and celebrated chefs. Explore 17 diverse climate-controlled grow rooms and follow every stage of the mushroom-growing process—from spore to harvest. Experience how advanced agricultural technology produces sustainable, flavorful mushrooms that grace everything from tacos to fine dining plates. This behind-the-scenes adventure is perfect for food lovers and curious minds, offering an unforgettable look at the future of farming and flavor.

Admire up-close views of the Chicago skyline—and a fireworks show over the city—on this tiki bar boat tour. In the evening, make your own way to the departure point at the Chicago Riverwalk, hop aboard, and get comfortable in the air-conditioned seating area or on the deck. Purchase cocktails and food from the on-site tiki bar, watch the city float by, and then sit back and take in the show.

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!

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.

On this cheerful tour you’ll see Chicago’s most famous Christmas trees, as well as several under-the-radar ones you may not know about. Your guide will lead you around downtown, stopping at the Christkindlmarkt and the old Marshall Field’s, as well as hidden-gem spots with some of the city’s most impressive holiday decor. All the while, you’ll learn about some beloved Christmas stories and traditions from across the globe, and even get to stop for some holiday sweets.

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district, now becoming the Chicago Brewery District. Here you'll experience the fabulous, intricate world of the art of beer creation. We will all meet at the first one, introduce ourselves and try some delicious appetizers; where Carla will make a special Homemade Guacamole and Homemade Tortilla chips, and here, the first 3 handcrafted beers (3-5oz beers) are on us. Then we'll walk to the other breweries where you'll have a chance to order other beers and serve your own. Here you can stay as long as you want after the tour. During our expedition, we can all share our opinion about the flavors, the creation, etc... All the breweries are within walking distance.

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn fascinating stories about the city’s history and culture. At each stop, professional photos will be taken of you or your group, allowing you to take home original digital images that capture your adventure in the Windy City. - Visit five picturesque locations for memorable photos - Enjoy breathtaking skyline views throughout the tour - Receive original digital photos after the tour to keep the memories alive - Perfect for couples, families, or anyone wanting to explore Chicago through photography

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous past as you explore the sites connected to America’s most notorious serial killers — John Wayne Gacy, the “Killer Clown” who haunted the Chicago area, and Jeffrey Dahmer, whose gruesome acts shocked the nation.

Explore the Chicago History Museum on a private tour customized for you. Benefit from expert commentary that brings the city's history to life while providing richer context behind the museum's collections and exhibits. The intimate format allows a flexible pace, deeper interaction with your guide, and the opportunity to focus on the stories and topics that interest you most.

Milwaukee offers a wide range of sightseeing highlights and cultural attractions—but it can be challenging to find your own way there from Chicago. Instead, leave the logistics and transit to someone else, and enjoy a hassle-free way to explore, on this small-group day trip. Opt for a cost-effective tour-only option to visit key city sights, or upgrade to add admission to the Harley-Davidson Museum and Miller Brewery or Pabst Mansion.

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.

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.

An immersive clue-solving adventure around the trendy arts neighborhood Fulton Market. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll never forget! Reschedule anytime with no fees. It's a scavenger hunt, escape room, and urban crawl all-in-one. Follow the storyline around town as you find clues and use them to crack codes. Then enter solutions on the app to find out where to go next. Clues can be anywhere - murals, statues, landmarks, and more! Plan on about two hours of playtime, depending on your experience level and how much time you spend exploring along the way. Difficulty level is adjustable - take as many or as few hints as you’d like! PLEASE NOTE: Bookings made less than 7 days before your play date will be scheduled for local pickup. For bookings made 7+ days in advance, our team will contact you to arrange shipping.

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.

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes provide effortless rides through the city, eliminating worries about traffic and parking. Experience the joy of biking while saving on gas and insurance costs. - Convenient location on Clark Street in Lincoln Park - Free demo test ride available - Ideal for leisurely exploration or thrilling rides - Expert advice to help you choose the right e-bike model

Enjoy a new perspective on the Windy City—and see more of its sights in less time, all without breaking a sweat—on this small-group, sunset Segway tour. With included instruction and hands-on guidance, get comfortable on your Segway in no time. Then, set off to discover top Chicago highlights from the Museum Campus and Millennium Park to Buckingham Fountain and beyond, all while the city's lights slowly come on.