The 7 Best Tour Operators in Chicago

Discovering the vibrant city of Chicago is best done with the expertise of a professional tour operator. Whether you’re a local looking to explore hidden gems or a visitor eager to see iconic landmarks, choosing the right tour service can make all the difference. In this guide, we highlight the 7 best tour operators in Chicago, known for their exceptional service, knowledgeable guides, and unique experiences.

When selecting a tour operator, consider the following services and aspects:

Customized Tours: Tailored experiences to fit your interests and schedule.
Group Tours: Join others for a shared experience, often at a lower price.
Private Tours: Enjoy a more personalized and intimate exploration.
Guided Walking Tours: Discover the city on foot with expert insights.
Bus Tours: Cover more ground and see more sights in comfort.
Specialty Tours: Focus on specific interests, such as architecture, food, or history.
Pricing: Consider the cost, which can vary from $20 to several hundred dollars, depending on the type and duration of the tour.
Reputation and Reviews: Look for operators with positive feedback and a strong reputation.

Each tour operator in our guide offers something unique, ensuring that your Chicago adventure is memorable and enriching. Whether you’re drawn to the bustling downtown or the serene lakefront, these expert operators will enhance your experience with their deep knowledge and passion for the Windy City.

1. Chicago Segway Tours
2. Chicago Detours
3. Vacations by Rail

4. Chicago Prohibition Tours
5. Nightly Spirits
6. Chicago Food Planet
7. Two Lane America

Number of companies

1310

Verified reviews

4,77

Average rating

(312)8903701

1. Chicago Segway Tours

★ ★ ★ ★ ★ 4,5/5

505 N DuSable Lake Shore Dr, 60611.0, Chicago

Tour operator
Tourist attraction

Why we chose them

Chicago Segway Tours offers a unique way to explore the vibrant cityscape, providing an unforgettable experience for both tourists and locals. Their tours, such as the Lakefront & Museum Campus Tour and the exhilarating Glide@Nite, showcase Chicago’s scenic beauty and lively atmosphere. With packages tailored to beginners and seasoned riders alike, this tour operator ensures that every participant feels comfortable and engaged. The company prides itself on offering the guaranteed lowest prices in town, making it an affordable adventure for everyone.

Known for their first-class service and thorough training, Chicago Segway Tours has received rave reviews from participants who appreciate their attention to detail and commitment to safety. The staff is friendly and skilled, making sure that each ride is both fun and informative. Their tours provide spectacular photo opportunities, making them perfect for capturing memories of the city. Whether it’s a corporate outing or a private exploration, this company ensures a memorable experience with every glide through Chicago’s open-air museum of attractions.

(312)3501131

2. Chicago Detours

★ ★ ★ ★ ★ 4,9/5

935 W Chestnut St #405, 60642.0, Chicago

Tour operator
Consultant
Event planner

Why we chose them

Chicago Detours stands out as a boutique experiential company renowned for its ability to connect people with their surroundings through immersive storytelling and interactive activities. They offer a diverse range of services, including tour operations, consultancy, and event planning, catering to corporations, universities, and museums. Their unique approach involves community-building activities that weave Chicago’s rich stories into engaging experiences. From visitor experience strategies to corporate field immersions and experiential learning programs, they craft custom in-person and virtual tours that captivate audiences with themes such as women’s history, the 1893 World’s Fair, and the Chicago River.

The company is celebrated for its innovative use of storytelling, with a team comprising educators, historians, journalists, and creators who excel in producing hyperlocal stories through visual, written, and experiential media. Their virtual experiences feature stunning visuals and dynamic storytelling, allowing guests to traverse time and space with historic illustrations and 360-degree photos. Notably featured in Entrepreneur Magazine, they also offer creative challenges and competitive games to foster remote collaboration. Known for having some of the best tour guides and incredible storytellers, they have successfully transitioned from a traditional tour company to an expert in creating and curating digital content like virtual tours and documentary videos.

(877)9297245

3. Vacations by Rail

★ ★ ★ ★ ★ 4,5/5

309 W Washington St # 1100, 60606.0, Chicago

Tour operator
Tour agency

Why we chose them

Vacations By Rail stands out as North America’s most comprehensive provider of global rail travel and tours, offering a unique way to explore destinations across the globe. With a vast selection of independent rail vacations, escorted rail tours, luxury rail journeys, and custom train vacations, the company caters to a wide array of travel preferences. Whether exploring the scenic landscapes of the United States, the vibrant cultures of Europe, or the majestic Canadian Rockies, travelers can find thoughtfully planned itineraries that promise unforgettable experiences. Their expertise as a trusted authority on rail vacations ensures that every journey is both seamless and enriching.

As a leading tour operator and tour agency, the company offers exceptional customer service backed by over 20 years of experience in the travel industry. Their dedicated rail specialists provide expert guidance and support, ensuring that each trip is tailored to meet the needs of their clients. The company also prides itself on offering the largest collection of vacation packages, including river cruises and escorted tours, allowing travelers to explore culture-rich cities and breathtaking landscapes. Highly rated by satisfied customers, the company continues to be a preferred choice for those seeking adventure and discovery by rail.

(630)9359428

4. Chicago Prohibition Tours

★ ★ ★ ★ ★ 4,8/5

27 N Wacker Dr #126, 60606.0, Chicago

Tour operator
Bar

Why we chose them

Chicago Prohibition Tours offers a captivating glimpse into the city’s notorious past through engaging guided bus and walking tours. Visitors are taken on a journey through the Prohibition era, exploring the infamous speakeasies that played a crucial role in Chicago’s history. The tours are rich with tales of gangsters, politicians, and the intriguing stories that unfolded during this tumultuous time. Guests can enjoy a drink or two along the way, making the experience both educational and entertaining. This unique approach to exploring Chicago’s history is why the company stands out as the top Prohibition tour in the city.

In addition to regular tours, the company provides opportunities to craft private events, perfect for company outings or special occasions. Their blog, filled with intriguing articles like “The Hush” and “A Toast to the Prohibition Movement and Its Epic Failures,” offers additional insights into the era, enhancing the overall experience. With a commitment to delivering thought-provoking and enjoyable tours, Chicago Prohibition Tours has garnered rave reviews from international travelers and locals alike, making it a must-visit for anyone interested in the fascinating stories of Chicago’s past.

(844)6788687

5. Nightly Spirits

★ ★ ★ ★ ★ 4,9/5

Tours meet inside Glascott's Saloon, 2158 N Halsted St, 60614.0, Chicago

Tour operator

Why we chose them

Nightly Spirits offers an enthralling journey into the eerie history of Chicago through its Haunted Pub Tours. With a costumed guide leading the way, participants embark on a 2.5-hour adventure filled with spine-chilling tales of long-dead phantoms and specters. The tour includes visits to several bars, where attendees can enjoy drinks at their own expense while delving into the city’s haunted past. Recognized as one of the Top 10 Best Ghost Tours in the United States, Nightly Spirits promises an unforgettable experience for ghost hunters, casual believers, and even skeptics.

Operating across numerous cities, including Chicago, the company has been voted Best Haunted Ghost Tour by USA TODAY for two consecutive years. Founded by two roommates with a passion for the paranormal, Nightly Spirits has grown to offer thrilling tours in cities like Austin, Boston, and New Orleans. Their commitment to providing a personal touch and high-quality experiences is evident through their multiple awards and hundreds of five-star reviews. Engaging promotions, such as discounts for special events and gift card bonuses, further enhance the appeal of their captivating tours.

(312)9320800

6. Chicago Food Planet

★ ★ ★ ★ ★ 4,8/5

600 E Grand Ave, 60611.0, Chicago

Tour operator

Why we chose them

Chicago Food Planet offers a unique way to explore the Windy City through its diverse and delicious food tours. As the original Chicago food tour operator, they provide an immersive experience that showcases the city’s iconic eats and hidden culinary gems. With expert guides who are passionate about Chicago’s food and history, they ensure both locals and visitors get an authentic taste of the city. Their tours cover a wide range of neighborhoods and cuisines, from the famed deep dish pizza and Italian beef to the vibrant flavors of Chinatown and the artistic vibes of Pilsen.

The company offers specialized tours such as the “Yes, Chef! Chicago: A Bear-Inspired Food Tour,” giving participants a chance to visit restaurants featured in popular media. With options for private experiences and corporate events, they cater to various group sizes and interests. The tours are designed to feel personal and engaging, avoiding the typical tourist traps and instead offering full-sized tastings that are the equivalent of a complete meal. Chicago Food Planet’s commitment to providing an authentic and enjoyable experience makes them a standout choice for anyone looking to explore the culinary heart of Chicago.

(513)8278273

7. Two Lane America

★ ★ ★ ★ ★ 5,0/5

1050 N Damen Ave, 60622.0, Chicago

Tour operator

Why we chose them

Two Lane America is a distinguished tour operator specializing in guided tours along the iconic Route 66 and other celebrated regions of the United States. The company offers a variety of travel experiences, including car caravans and bus tours, making the classic American road trip accessible and stress-free. Travelers can choose to drive their own vehicles in the company’s expertly organized car caravans or relax on a motorcoach while exploring destinations such as the scenic Southwest, the vibrant South from Nashville to New Orleans, and the picturesque fall landscapes of New England. With a focus on creating unforgettable road trip adventures, Two Lane America allows travelers to experience the unique charm and history of each destination.

Emphasizing ease and enjoyment, the company provides multiple guided tour options that cater to a wide range of interests. Whether it’s cruising the legendary Route 66 from Chicago to LA, delving into the Midwest’s rich automotive heritage, or marveling at the natural beauty of the Southwest, each tour is designed to offer a seamless and enriching travel experience. Two Lane America’s dedication to storytelling and adventure is further showcased through their engaging travel blog, “Tales from the Road,” which highlights unique attractions like the James Dean Museum. By making the great American road trip easier than ever, they deliver an adventure-packed journey filled with discovery and exploration.

FAQs

What types of tours do tour operators in Chicago offer?

Tour operators in Chicago offer a variety of tours, including customized tours, group tours, private tours, guided walking tours, bus tours, and specialty tours focusing on areas like architecture, food, or history.

How much do tours in Chicago generally cost?

Tour prices in Chicago can vary widely. On average, you can expect to pay between €18 and €200, depending on the type and duration of the tour.

How long do most tours in Chicago last?

The duration of tours in Chicago can range from a couple of hours to a full day. Walking tours might last 2-3 hours, while bus or specialty tours could extend to 6-8 hours.

What should I consider when choosing a tour operator in Chicago?

Consider the types of tours offered, pricing, the operator's reputation, reviews from previous customers, and whether they provide services that match your interests and schedule.

Are group tours in Chicago more affordable than private tours?

Yes, group tours are generally more affordable than private tours. They provide a shared experience with others, often at a lower price point.

What are the benefits of taking a private tour in Chicago?

Private tours offer a more personalized and intimate experience, allowing you to explore at your own pace and focus on specific interests with the undivided attention of your guide.

How can I find reputable tour operators in Chicago?

Look for operators with positive reviews, strong reputations, and recommendations from trusted sources. Online platforms and travel forums can also provide valuable insights.

Do tour operators in Chicago offer tours in languages other than English?

Many tour operators in Chicago offer tours in multiple languages. It's best to check with the operator in advance to ensure they can accommodate your language preference.