Tours
in Chicago, IL

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Plan for something nice during your next vacation, or maybe next time someone comes for a visit. Surprise your guests – or your traveling buddies – with professional tours of the area. Get to know the latest and greatest venues or historical spots, or maybe get a specialized tour and hit the best areas in the city.

Check out our list below to see everything that’s available in the area. Find their name, address, phone number, website and driving directions – and start your next adventure!
Bike and Roll Chicago
Bike and Roll Chicago

(312) 729-1000

700 E Grand Ave
Chicago, IL 60611   Directions Website

Bike and Roll Chicago offers several locations to rent bicycles or Segways to explore the city. They provide five different tour options, such as The Amazing Lakefront, Friendly Neighbors, Chicago River & Parks, The Presidential Tour, and Bikes @ Nite, so you can pick the one that best suits your interests.

Join one of their award-winning bike tours and see all the top attractions in Chicago. Glide along the stunning lakefront on a Segway. Please wear appropriate walking shoes as you embark on a magical adventure through downtown Chicago, lit with beautiful illuminations.

Chicago Architecture Center
Chicago Architecture Center

(312) 922-3432

111 E Wacker Dr Ste 1321
Chicago, IL 60601   Directions Website

Chicago is renowned worldwide for its architecture, and the Chicago Architecture Foundation offers a variety of tours to showcase some of the city's most exceptional buildings.

With walking, bus, and boat tours available, visitors can explore the downtown area or one of the city's many charming neighborhoods. Expert docents will guide you and share the stories behind the buildings, whether you visit iconic skyscrapers, elegant hotels, or legendary houses designed by Frank Lloyd Wright. With dozens of tours, you may need help selecting just one.

Chicago Pizza Tours
Chicago Pizza Tours

(312) 221-8502

27 N Upper Wacker Dr
Chicago, IL 60606   Directions Website

Are you looking for the ultimate pizza experience in Chicago? Look no further than the Chicago Pizza Tours. You'll be able to visit four of the city's top-rated, historic, and highly-reviewed pizzerias. At each of the carefully chosen locations, you can enjoy multiple styles of pizza and discover new places to add to your must-visit list. The tours are led by trained experts who will take you to off-the-beaten-path neighborhoods so you can eat like a local Chicagoan.

There are three tours: The Original Chicago Pizza Tour, a 3.5-hour daytime bus tour; The Downtown Pizza Walk, a 3-hour daytime walking tour; and the Bucktown Neighborhood Pizza Crawl, a 3-hour daytime walking tour. All food is pre-ordered and ready for your group when you arrive at each stop. They are also able to accommodate most dietary restrictions. In addition, alcohol is available for purchase at each stop. Take advantage of this fantastic pizza adventure.

City Experiences | Chicago Cruises, Boat Rides & Tours
City Experiences | Chicago Cruises, Boat Rides & Tours

(800) 459-8105

600 E Grand Ave
Chicago, IL 60611   Directions Website

Enjoy a memorable evening on the water with City Experiences Chicago Cruises, Boat Rides & Tours. With a perfect setting to enjoy dinner, drinks, and dancing, they provide stunning views of Chicago from the water.

City Experiences offers exciting options for groups of 20 or more, such as historic sightseeing cruises in Boston, thrilling speed boat rides on Seadog in Chicago or Codzilla in Boston, and awe-inspiring whale watches in San Diego or Boston. With unique tours and experiences, City Experiences ensures an unforgettable day on the water.

Segway Experience of Chicago
Segway Experience of Chicago

(312) 663-0600

2 E 8th St
Chicago, IL 60605   Directions Website

Are you looking for a fun and unique way to explore Chicago? Look no further than The Segway Experience of Chicago. You can rent a Segway and join a guided tour that will take you through some of the city's most iconic architecture and landmarks.

During the tour, you'll feel like a kid again as you glide through the streets on your Segway. Experienced and knowledgeable guides will lead you through scenic and historic downtown Chicago and popular destinations such as Grant Park, the Buckingham Fountain, the Museum Campus, and the lakefront. You can join the Riverwalk tour if you prefer to explore the Chicago River. You'll see Navy Pier and famous Chicago bridges, travel up historic Michigan Avenue, and pass by Millennium Park. Whichever tour you choose, The Segway Experience of Chicago guarantees it will be a lifetime memory.

Tall Ship Windy
Tall Ship Windy

(312) 451-2700

600 E Grand Ave
Chicago, IL 60611   Directions Website

Welcome aboard! Embark on an unforgettable skyline sail packed with unique experiences, including an architecture tour revealing the hidden history of the Windy City's skyline, thrilling pirate and maritime tales that transport you back in time, and educational sails that pique curious minds. Catch the breathtaking horizon views during sunset sails, creating the perfect backdrop for romantic moments, fun nights with friends, and stunning photo opportunities.

Join them for the Monday Night Blues sail, where live music will soothe your soul, or celebrate special occasions with enchanting fireworks sails that light up the night sky. At Windy, they aim to create memories, connect people, and provide an unparalleled nautical experience.

Tastebud Tours
Tastebud Tours

(219) 929-6648

Chicago, IL 60642
Website

Attention food enthusiasts in Chicago! Have you ever considered exploring the city's food, history, and architecture all in one walking food adventure? If so, Tastebud Tours is the perfect choice for you. Get ready to embark on a delicious journey through specialty dessert shops, famous deep-dish pizza joints, Chicago-style hot dog stands, and unique ethnic eateries.

Tastebud Food Tours strives to provide its guests with a world-class food tour experience of exceptional value. Their tour guides are the secret ingredient to their success, and they take pride in their spirit of loyalty, enthusiasm, and dedication.

Untouchable Tours
Untouchable Tours

(773) 881-1195

600 N Clark St
Chicago, IL 60654   Directions Website

Embark on a journey back in time to the days of infamous mobsters like Al Capone, Bugs Moran, and John Dillinger with Untouchable Tours. This unique experience takes patrons to various famous areas in Chicago where notorious gangsters would hang out during the days of Prohibition.

During the tour, you'll return to Prohibition-era Chicago and visit the hotspots where Al Capone and his allies and enemies became famous. The guides are actors who adopt the persona of a 1920s gangster and accurately recount the crimes and activities in Chicago during the 1920s and '30s. You'll hear about the exploits of Capone, Moran, Dillinger, and other notorious gangsters. Some sites included are the St. Valentine's Day Massacre, the Biograph Theatre, and Holy Name Cathedral. The tour is educational and highly entertaining, and you even have the chance to win prizes at the end.

Urban Kayaks
Urban Kayaks

(312) 965-0035

435 E Riverwalk S
Chicago, IL 60601   Directions Website

Are you looking for a unique and exciting way to experience Chicago? Look no further than Urban Kayaks, offering downtown guided kayak tours and rentals for all skill levels. Whether you're interested in the famous sunset kayak trip or the historic Chicago kayak tour, there's something for everyone. Enjoy the beautiful sunset or watch the Navy Pier fireworks display during your kayaking adventure on the Chicago River.

The experience offered by Urban Kayaks showcases the city of Chicago amazingly and uniquely. You'll leave with a smile, from the courteous and helpful staff to the lovable pooches hanging out at the shop. They love Chicago and can't wait to take you on a tour that will inspire adventure and show you the best of the city.

Wendella Tours & Cruises
Wendella Tours & Cruises

(312) 337-1446

400 N Michigan Ave
Chicago, IL 60611   Directions Website

For over 80 years, Wendella has been Chicago's top provider of tours and cruises on the River and Lake Michigan. Their tours offer the perfect blend of nostalgia for the city's rich history and modern experiences, making it an enjoyable day on the water for visitors and locals alike.

As the original architecture tour in Chicago, Wendella offers a variety of narrated tours that focus on the city's architectural heritage and history. Their knowledgeable tour guides provide detailed accounts of the 130-year-long history behind the iconic skyline, while the staff ensures that you are comfortable and entertained throughout the journey. This tour takes you through the city's heart on all three branches of the Chicago River, providing an up-close look at the iconic buildings and structures that define the city.

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