The Magnificent Mile
Tours

Enter your dates to find available activities

Our most recommended The Magnificent Mile Tours

Chicago: Mob and Crime Bus Tour

1. Chicago: Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

2. Chicago: 1.5-Hour Open-Top Double-Decker Night Tour

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 75-minute, live-guided panoramic tour and take in unique views of the Chicago Skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off of The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper and see architectural marvels like 875 N Michigan Ave (formally the John Hancock Building), the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. End the tour at the Chicago Riverwalk, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers, to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

Chicago Crimes Night Tour

3. Chicago Crimes Night Tour

Uncover how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the Windy City. Ride in luxury on a climate-controlled bus, as you explore famous Chicago crime scenes ranging from the 19th century through to modern times. Learn about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, The Lady in Red, Captain George Streeter, Frank "The Enforcer" Nitti, Bugs Moran, Johnny Torrio and more. Grab your camera for a drive-by shooting of historic and architectural landmarks, and stake out crime scenes like the Biograph Theatre, Holy Name Cathedral and St. Valentine's Day Massacre, one of Chicago's most notorious murder sites. Walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

4. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: Food, History and Architecture Tour with Tastings

5. Chicago: Food, History and Architecture Tour with Tastings

Discover the best of Chicago on a comprehensive guided tour. Learn more about the city's history and vibrant food scene as you discover various bustling neighborhoods and historic areas. Start your tour under the dazzling marquee of the Chicago Theater, recognizable from movie-musical Chicago before heading off into the bustling city. First, stop at the Chicago Pedway, used by locals and commuters daily to move about the city in a network of underground tunnels. From here, head towards the official seat of the government for the city at City Hall. Check out its classic interior design and architecture.  Next, enjoy your first food tasting of the day, traditional Chicago-style popcorn. Weather permitting, your guide will take you for a stroll along the Chicago Riverwalk, pointing out familiar buildings such as the Marina Towers, the Britannica Building, and the Willis Tower. From here, make your way to another delicious destination where you can sample locally made chocolate from a local shop.  Then, you will either hop on the ‘L’ train or a water taxi on the Chicago River, depending on the weather and time of year. Either option offers a uniquely local Chicago experience. Feel like a local as you zip past buildings and catch even more awesome views. Next, take a stroll through the beautiful lakefront parks along Michigan Avenue. Arrive at the picturesque Millennium Park, home to the iconic Bean sculpture. By then, you’ll hopefully have built up an appetite because it’s time to begin your ultimate food experience. Travel with your guide up to the River North neighborhood, the original Chicago foodie destination. Your first food sampling is a local favorite, a Chicago-style hot dog. Next up is the world-famous Chicago deep-dish pizza, the staple of the Chicago food scene. Visit a pizza place that’s an icon to Chicago natives to try the real deal for yourself. After you’ve filled up on pizza and hot dogs, take a stroll through two more establishments, each one essential to Chicago’s food culture. Then continue your tasting journey with a classic Chicago sandwich: Italian beef. Sample this sandwich in a true Chicago institution. Your tour ends here, but don’t forget to get some recommendations from your guide of where else you visit or eat during tour time in the city.

Chicago: Riverwalk Guided Walking Tour

6. Chicago: Riverwalk Guided Walking Tour

Tag along on this essential Chicago experience: a guided walking tour of the Chicago Riverwalk. Spend your day exploring art, architecture, and all the locals’ favorite spaces. Visit the Meatpacking District, Chelsea Market, DuSable Bridge, and more. Birthed around the banks of the (now) Riverwalk, Chicago is a city teeming with tales. With the help of your local guide, discover the stories behind the sites you visit and see. Visit all four districts of the Riverwalk, each offering its own flavor of Chicago. Pass iconic sites including the Wrigley Building, Tribune Tower, DuSable Bridge, and the Marina Towers. As an added perk, become a Chicago insider with behind-the-scenes access at the McCormick Bridgehouse & Chicago River Museum. Stop at Heald Square and see the city’s many monuments and memorials. Along the tour, spot the touching Vietnam Veterans Memorial. Continue strolling down the Riverwalk and hear stories at the site of Old Fort Dearborn and the disaster that was the SS Eastland. Then, pass by the Jeweler's Building and find out if Al Capone really had a super-secret speakeasy at the very top. Nearing the end of the tour, take in a Picasso gifted to the city by the artist himself, see the first church at the Chicago Temple, and end under the prisms of light filtering in the Tiffany Dome at the Chicago Cultural Center.

Chicago: Private 3-Hour Al Capone Gangster Tour

7. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

Chicago: Private Architecture Tour - 3 or 6 Hours

8. Chicago: Private Architecture Tour - 3 or 6 Hours

Start with pickup from your hotel and meet your local tour guide, an expert on the architecture of Chicago. Travel through the city in luxury private transportation to discover its rich architectural history. See famous buildings such as the Sears Tower, The John Hancock Building, and the Wrigley Building Discover Gothic gems along the Magnificent Mile, historic brownstones, and the Frank Lloyd Wright homes of Oak Park. Enjoy a unique added value opportunity to view not only the outside but the amazing hidden interior of many of the buildings on the tour. At your discretion, make numerous stops along the tour to go to the top of the sky decks of famous skyscrapers. Walk along the Chicago River and enter the inside of buildings designed by many famous architects. This tour has several different options. Enjoy the sites of the downtown Chicago area with its many skyscrapers, amazing interiors and great photo opportunities. You may also choose the Oak Park Frank Lloyd Wright Homes and Studio option in lieu of the downtown tour where you will have the opportunity to view the interior of his very first home and studio along with over two dozen of his original structures lining Forest Street in Oak Park anchored by Unity Temple, considered to be the world's first building of the modern architectural style. Each of the above separate options are 3 hours long. If you are to choose both options for a full 6-hour touring experience, enjoy a lunch stop at one of Chicago's many famous hot dog stands or deep-dish pizza joints.

Chicago: Private Half-Day Highlights Tour with Hancock Tower

9. Chicago: Private Half-Day Highlights Tour with Hancock Tower

Explore Chicago, a vibrant metropolis packed with incredible history, architecture, and public art. Discover the third-largest city in the United States on a guided walking tour. Visit all of the city's major sights, such as the Magnificent Mile, Navy Pier, Millenium Park, and Hancock Tower. Listen to stories about Chicago life from a local and find out how the city earned its nicknames. Savor a slice of deep-dish pizza at the end of your tour before your guide drops you off at Hancock Tower. Enjoy 360-degree views of the city from the observation deck.

Frequently asked questions about The Magnificent Mile Tours

What are other things to do than Tours that are worth visiting in The Magnificent Mile?

The other unmissable things to do in The Magnificent Mile are:

Which The Magnificent Mile Tours are taking additional COVID-19 precautions?

Other Sightseeing Options in The Magnificent Mile

Want to discover all there is to do in The Magnificent Mile? Click here for a full list.

What people are saying about The Magnificent Mile

Overall rating

4.0 / 5

based on 417 reviews

Had a really enjoyable time , our guide was Jay she was really entertaining gave us loads of information and made it a fab tour which I would highly recommend . Jay was engaging from the start of the tour until the end and seemed to enjoy it as much as we did . Well done !!

Fun, informative, very tasty tour. Dylan, the guide, was knowledgeable and super fun.

Justin was phenomenal! So enthusiastic about the city. Made it so fun! Also, the food

VERY VERY INTERESTING THE WHOLE TIME!!! AWESOME!!! Def Recommend!!! book early!!

차타고 편히 돌아다닙니다. 가이드도 상냥하고 혜자네요. 갱이랑 범죄에 관심있으시면 좋을것 같습니다.