Tour-tally Awesome: 14 Must-Try Tour Operators in Chicago!

Chicago is a vibrant city with a lot to offer. From its stunning architecture to its delicious food, there's no shortage of things to see and do. And when it comes to exploring this great city, tour operators are an excellent option.

They offer visitors a chance to see the city through the eyes of a local and take advantage of their extensive knowledge of the area. But with so many tour operators to choose from, it can be overwhelming to find the right one for you.

That's where this guide comes in. We've done the research and compiled a list of the best tour operators in Chicago.

Whether you're interested in a walking tour of the city's historic neighborhoods or a boat tour along the Chicago River, we've got you covered. Our list includes a variety of tour operators, each with their own unique offerings and specialties.

But why choose a tour operator in the first place? Well, for starters, tour operators can save you time and hassle. They'll take care of all the logistics, so you can sit back and enjoy the ride.

They also provide an opportunity to learn from experts who are passionate about the city and its history. Plus, tours can be a great way to meet other travelers and make new friends. So without further ado, let's dive into our list of the best tour operators in Chicago.

1. Chicago Gangsters and Ghosts Tours

Chicago Gangsters And Ghosts Tours
71 East W Wacker Dr, Chicago, IL 60601 (Google Maps)

Chicago Gangsters and Ghosts Tours is a highly recommended tour operator for those who want to explore the city's history and spooky side.

The knowledgeable and energetic guides make the tour engaging and informative, providing extra tidbits of information beyond the usual storytelling.

The walking tour is well-paced, allowing for time to take photos and admire the landmarks.

The tour is a great way to learn about Chicago's architecture, society, and events. The tour is suitable for families and groups of friends looking for a unique experience.

2. Chicago Detours

Chicago Detours
53 W Jackson Blvd # 1357, Chicago, IL 60604 (Google Maps)

Chicago Detours is an event management company that offers various sightseeing tours and event planning services.

Their knowledgeable guides provide dynamic and interactive tours that take visitors to lesser-known spots around the city. The tours cover a range of topics such as Chicago's history, architecture, and the impact of the 1893 World's Fair.

The company also offers virtual tours, which are perfect for those who cannot visit the city in person.

The tours are informative, fun and perfect for both locals and visitors. Chicago Detours is a must-try for anyone looking for a unique and engaging way to explore the city.

3. Chicago Greeter

Chicago Greeter
72 E Randolph St, Chicago, IL 60601 (Google Maps)

Chicago Greeter is a highly recommended tour operator that offers personalized walking tours of Chicago.

Their knowledgeable and friendly guides provide insightful information about the city's history, architecture, and culture.

The company also offers free customized tours for those who contact them two weeks in advance.

This is a great option for anyone looking to explore Chicago in a unique and informative way.

4. See Sight Tours – Chicago Tours

See Sight Tours - Chicago Tours
200 E Randolph St Suite 5100, Chicago, IL 60601 (Google Maps)

See Sight Tours – Chicago Tours is a popular tour operator that offers a variety of tours for visitors to the city.

With knowledgeable and personable guides, they provide a fun and informative experience for all.

The tours cover the must-see spots in the city with interesting background stories and observations. The guides are also happy to help with taking photos.

The tour is highly recommended by many visitors and is a great way to see the city in a short amount of time.

5. Chicago Foodways Tours

Chicago Foodways Tours
see Web Site for Tour Locations, Chicago, IL 60640 (Google Maps)

Chicago Foodways Tours is a top-notch tour operator that offers food and drink tours in the city.

Led by Phyllis, who is incredibly knowledgeable and passionate about food and the neighbourhoods the tours are in, their Saigon to Stockholm tour is highly recommended.

The tour includes a recap email of everything tasted, making it easy to relive the experience. The Little Italy tour is also a must-try.

Whether you're a local or a tourist, Chicago Foodways Tours is the perfect way to explore the city's food scene.

6. Two Lane America

Two Lane America
1050 N Damen Ave, Chicago, IL 60622 (Google Maps)

If you're looking for an exceptional tour operator in the US, Two Lane America is one to consider.

Their Route 66 trip from Chicago to Los Angeles is a highlight for many travelers, thanks to the exceptional planning and attention to detail provided by Austin Coop.

He is a people person, always willing to go the extra mile to ensure his guests are satisfied.

Whether you're a seasoned traveler or a first-timer, Two Lane America is a great choice for a memorable trip.

7. Chicago Private Tours

Chicago Private Tours
900 Michigan Ave, Chicago, IL 60611 (Google Maps)

Chicago Private Tours is a great option for those looking to explore the city in a unique way.

Their private tours are led by knowledgeable guides who offer a crash course on the city's history and attractions.

The tour is conducted in a comfortable vehicle, making it easy to see the sights without the hassle of navigating public transportation.

The tour is customizable, so visitors can see the sights they are most interested in. The tour is a great way to get a taste of what Chicago has to offer and leaves visitors wanting to come back for more.

8. Chicago Private Tours and Productions

Chicago Private Tours And Productions
116 W Chestnut St, Chicago, IL 60610 (Google Maps)

Chicago Private Tours and Productions is a top-rated tour operator that offers custom tours in Chicago.

Their excellent communication before the tour helps guests to develop a tour that is meaningful to them.

The knowledgeable and friendly tour guides make the experience relaxing and enjoyable. The company's amazing drivers ensure a smooth ride throughout the tour.

Chicago Private Tours and Productions is highly recommended for those looking for an unforgettable tour experience in Chicago.

9. Chicago Prohibition Tours

Chicago Prohibition Tours
27 N Upper Wacker Dr #126, Chicago, IL 60606 (Google Maps)

Chicago Prohibition Tours offers an exciting and unique way to learn about the city's history. With knowledgeable and friendly guides, guests are taken on a walking tour to visit various bars with VIP access.

The tour offers an interesting mix of history and drinks, making it a fun experience for adults.

The group sizes are perfect, and the atmosphere is friendly and fun. The tour is definitely worth the money and leaves guests wanting more.

With great drink recommendations and a wealth of knowledge about the prohibition era and gangsters, Chicago Prohibition Tours is a must-do experience for anyone visiting the city.

10. Chicago Food Planet

Chicago Food Planet
600 E Grand Ave, Chicago, IL 60611 (Google Maps)

Chicago Food Planet is a tour operator that offers food tours in the city. Their tours are highly recommended by visitors and locals alike.

The tour guides are knowledgeable, friendly, and engaging, making the experience delightful. The food selections on the tours are amazing, and the overall experience is super enjoyable.

They offer a beverage package with their tours, which is a nice touch. The only suggestion is to add one more food stop and one less sweet.

If you're looking for a fun and delicious way to explore the city, Chicago Food Planet is the tour operator for you.

11. Chicago Crime Tours and Experiences

Chicago Crime Tours And Experiences
163 E Pearson St, Chicago, IL 60611 (Google Maps)

Chicago Crime Tours and Experiences offers a fascinating and entertaining tour of downtown Chicago.

The knowledgeable and energetic tour guides provide insight into the city's criminal history and take visitors to some of the most infamous crime scenes.

The air-conditioned bus is comfortable and the driver keeps guests safe in the busy Chicago traffic.

The tour is COVID-friendly and a great value for the money. Highly recommended for anyone interested in the history of the "Windy City."

12. Vacations By Rail

Vacations By Rail
309 W Washington St # 1100, Chicago, IL 60606 (Google Maps)

Vacations By Rail is a reliable tour operator that provides excellent service and value. Their staff is helpful, patient, and communicates well with clients.

They offer a variety of train tours and have knowledgeable agents who can answer any questions or concerns.

They have a good track record of following up with clients and ensuring that everything runs smoothly.

If you're looking for a unique and exciting vacation experience, consider booking with Vacations By Rail.

13. Chicago Hajj & Umrah

Chicago Hajj & Umrah
2818 W Peterson Ave, Chicago, IL 60659 (Google Maps)

Chicago Hajj & Umrah is a highly recommended tour operator for those seeking Hajj or Umrah packages. They offer excellent communication and great service, making the process simple and fast.

Customers have praised their commitment to customer satisfaction and willingness to find good ticket prices with short layovers.

The visa process is efficient, with fast turnaround times and the convenience of uploading documents online.

Chicago Hajj & Umrah is a reliable choice for those planning a pilgrimage to Saudi Arabia.

14. Chicago Segway Tours

Chicago Segway Tours
505 N Lake Shore Dr, Chicago, IL 60611 (Google Maps)

Chicago Segway Tours offers an exceptional experience for anyone looking to explore the city in a unique way.

With a thorough training session, friendly and knowledgeable guides, and newer Segways with custom colors, this tour operator guarantees the lowest prices without compromising on quality.

The tour offers stops for photos and a good history of Chicago, making it an informative and fun activity for all ages.

Highly recommended for anyone looking for a memorable and exciting way to see the city.