Chicago-Style Holiday Hike: Festive Food and Walking Tour
There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holiday Hike, a 3-hour guided walking and food tour of the city’s top seasonal attractions.
You’ll sample Chicago favorites like deep-dish pizza, a Chicago-style hot dog, Italian beef, a chocolate brownie, and hot apple cider. Alcoholic beverages aren’t included, but holiday drink pairings can be added on-site.
Our local guides will fill the tour with festive stories—like how Rudolph the Red-Nosed Reindeer originated in Chicago. You’ll see the classic holiday windows at the original Marshall Field’s, the Chicago Christmas tree, the Millennium Park ice rink, and enjoy VIP entry to the Christkindlmarket.
No other tour offers such a complete Chicago holiday experience!
Historical and Architectural Chicago Fireboat River & Lake Cruise
Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin.
Bike Tour of Chicago's Lakefront Neighborhoods
This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods Chicago Bike Tour is what started it all. Join one of Bobby’s expert guides on this 3-hour bicycle tour through Chicago’s beautiful North Side Lakefront neighborhoods. See the ever-rising skyscrapers of Streeterville, the deluxe residential mansions of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the world-famous Lakefront Bike Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime! This Bicycle Tour of Chicago is kid-friendly and all equipment (bikes, helmets) is included.
Vito's Vault Chicago Speakeasy Dinner Theatre
One of the most unique experiences in Chicago. Immerse yourself in the Roaring Twenties. Step back in time to Prohibition Chicago with da gangsters and da flappers, and your host, Vito Valentino. Great music, great food, great comedy, and a great time, not to mention Vito's bootleg hooch. Give da password at the door, but when you're in, you're in.
Chicago Insider Segway Tour
This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!
Chicago Walking Tour: Must-See Chicago
Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and more!
Get a brief overview of more than a dozen buildings—as well as Chicago landmarks like Millennium Park, the Loop and the Chicago River—on this whirlwind tour. There are lots of photo opportunities along the way, so be sure to bring your camera!
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Chicago Walking Tour: The Magnificent Mile
Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons.
Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside.
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich
On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city.
You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!
Chicago Pizza Tour
Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza. Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias. In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
Chicago Fire TV Show Set Tour
Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes to life.
Tour Highlights:
- Explore the iconic Firehouse 51 exterior
- Visit the Molly's Bar a fictional bar on the show, but a real pub in Chicago.
- Visit the famous Bean (Cloud Gate) at Millennium Park
- Visit the Chicago Cultural Center renowned for its stunning architecture, including the world's largest Tiffany stained-glass dome.
This tour is subject to filming schedules, and it can be customized to your needs. Tour participants are respectfully advised that this is an active firehouse; please be mindful of operations and follow guidelines, noting that the tour is independently operated and separate from the fire department.
Additionally, For visits to Firehouse 51, the Bean, and the Chicago Cultural Center, please note that the tour guide will not accompany visitors, but detailed instructions will be provided.
Chicago Pier Fireworks Segway Tour
See Chicago's weekly summer fireworks display on this spectacular Chicago Segway Tour. You haven't seen Chicago until you have seen it at night while gliding through the park & lakefront on a Segway PT. View Buckingham Fountain's romantic evening light show with the illuminated skyline as a backdrop. This evening fireworks tour glides along the lakefront to our secret spot for watching Navy Pier's Fireworks display. It's difficult to decide which is more spectacular — the fireworks or the Chicago skyline in its evening splendor! A perfect family activity, this is one of our most fabulous Chicago Segway tours.
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hear of hidden mob headquarters, psychopaths in plain sight, and disasters like the Iroquois Fire and Eastland Disaster.
Join us in exploring historic interiors where gangsters once gathered and ghosts are said to linger. Along the way, explore the roots of ghost lore—are they real sightings or tricks of architecture? Decide for yourself if Chicago’s most haunted tales are fact or fiction. Perfect for fall nights and curious minds, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience.
Chicago Architecture Tour: Underground Pedway and the Loop
This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!
Chicago City Minibus Tour
Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more!
Along the way, your guide will provide historical and informational and at times humorous commentary about the area and its many attractions. The small-group atmosphere with maximum of 13 people ensures a more personal experience.
Please note, infants 0-3 years must sit on a lap.
Chicago Perfume Making Classes on Magnificent Mile
Step into the world of perfumery and unleash your creativity in a guided workshop! Explore a treasure trove of fragrance notes, from vibrant florals to exotic spices. With expert guidance, blend and harmonize these scents to craft a perfume that embodies your unique essence. Fill a luxurious 1.0oz bottle with your bespoke creation, personalized with a name or initials of your choice. Immerse yourself in this sensory journey, where every drop tells your story. Perfect for indulging solo or sharing with friends—an unforgettable experience awaits!
Outdoor Escape Room in Chicago - Fulton Market
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.
Luxury Minibus Chicago City Tour
Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus designed for comfort and class.
Marvel at iconic skyline views and the shimmering waters of Lake Michigan from panoramic windows, and enjoy curated photo stops at the city's most breathtaking landmarks. With engaging stories from your private guide and an intimate, upscale atmosphere, this tour offers an unmatched blend of elegance and exploration.
Please note, infants 0-3 years old must sit on a lap.
Lincoln Park Hauntings Ghost Investigation Tour
We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal researcher and investigator. Like Ursula, all of our guides are all real investigators and true Chicagoans. We love investigating, we love Chicago history, and we would love to show you Chicago's haunted history. This is the only tour which takes you out of the downtown area and into one of the most haunted parts of Chicago: Lincoln Park, the old City Cemetery, which was ravaged by the Great Fire of 1871, leaving 10,000 graves behind. The bodies are all still here, as well as the ghosts. The tour also visits the site of the St. Valentine's Day Massacre and the site of Suicide Bridge, where more than 100 desperate souls lost their lives.
Trickery Chicago Magic Show
Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious.
Theater is located at 3453 N Halsted Street (near the SE corner of Cornelia Ave). Door opens 15 minutes before showtime and seating is general admission.
Venue is BYOB for guests 21+. Cups and bottle openers are available if needed. We do not stock ice but there is a 7-Eleven just down the street (3407 N Halsted). Performance runs approximately 1 hour.
The Christmas Tree Crawl Experience Chicago at the Holidays
On this nostalgic and educational tour, we will lead you on a "Christmas treasure hunt" through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown. You’ll learn about the origins of some world-famous Christmas characters — some of them from Chicago, some not — as well as the history behind Christmas traditions practiced by people around the world.
Chicago Loop Walking Tour
The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. Along the way, we'll discuss some of the people, and people groups, that have helped to make this one of the "must see" communities, in Chicago!
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people overlook on a daily basis. We hope you join us to experience something truly unique in Chicago.
Chicago's Secret Interiors Architectural Walking Tour
We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking hidden spaces, from Frank Lloyd Wright’s sunlit masterpiece inside the Rookery to the world's largest Tiffany stained-glass domes at the Cultural Center and Marshall Field Building.
Walk through the stunning Gilded Age luxury of the Palmer House and iconic movie backdrops along La Salle Street at a relaxed, conversational pace. We combine world-class history with photo vantage points, ending with personalized local recommendations. Don’t just see Chicago, experience it from the inside out.
Chicago Walking Tour: Modern Architecture
Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) and a city ready and willing to accept them. Find out what set these buildings apart from their predecessors and how they helped set the stage for the future.
If you’re interested in iconic buildings, public art, urban planning or government this is your tour. Find out the stories behind inland steel, Marina city, the IBM building and other "Mad Men" worthy skyscrapers.
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.