The 7 Best Travel Agencies in Chicago

Chicago, the bustling metropolis by Lake Michigan, offers an array of exciting travel opportunities both locally and globally. Whether you’re planning an exotic getaway, a business trip, or a family vacation, finding the right travel agency can make all the difference. In this guide, we’ll explore the 7 Best Travel Agencies in Chicago, each offering unique services to meet your travel needs.

A travel agency can provide a wide range of services, ensuring a seamless and stress-free travel experience. Here are some services you might expect:

Flight Booking: Assistance with finding the best flight options and competitive pricing.
Accommodation Reservations: Booking hotels, resorts, or vacation rentals tailored to your preferences.
Travel Packages: Customized vacation packages that include flights, accommodations, and activities.
Travel Insurance: Providing options for travel insurance to protect against unexpected events.
Visa Assistance: Guidance and support in obtaining necessary travel visas.
Local Tours and Excursions: Arranging guided tours and activities at your destination.
Transportation Services: Coordinating car rentals, airport transfers, and other transportation needs.

When selecting a travel agency in Chicago, consider the following aspects to ensure a perfect fit:

Reputation and Reviews
Experience and Expertise
Customer Service Quality
Range of Services Offered
Pricing and Value for Money
Flexibility and Customization Options

With the right guidance and support, your next adventure could be just around the corner.

1. Chicago's First Lady
2. Chicago River Boat Architecture Tours
3. Chicago Helicopter Experience

4. Absolutely Chicago Segway Tours
5. Chicago Fireboat Tours
6. Untouchable Tour
7. Windy City Ghosts

Number of companies

7821

Verified reviews

4,80

Average rating

(847)3581330

1. Chicago's First Lady

★ ★ ★ ★ ★ 4,8/5

112 E Wacker Dr, 60601.0, Chicago

Boat tour agency
Event venue
Wedding venue

Why we chose them

Chicago’s First Lady offers an unparalleled way to experience the Windy City’s stunning architecture and vibrant waterfront. Known for the top-rated Chicago Architecture Center River Cruise, this boat tour agency provides an immersive journey through downtown Chicago’s architectural marvels. Guests can enjoy the renowned daytime river cruise or opt for an enchanting evening experience as the city transitions from day to night, casting golden hues over its iconic skyline. The fleet, reminiscent of 20th-century luxury yachts, adds a touch of elegance and charm, enhancing each voyage along the historic Chicago River.

Beyond its acclaimed tours, Chicago’s First Lady serves as a premier event and wedding venue, offering a unique setting for memorable occasions. Whether hosting a business gathering or celebrating a wedding, the seven exquisitely designed ships provide the perfect backdrop, combining the beauty of the river with exceptional service. The company emphasizes creating unforgettable experiences, making it a standout choice for anyone looking to explore Chicago’s hidden gems or celebrate significant milestones in style.

(708)4886343

2. Chicago River Boat Architecture Tours

★ ★ ★ ★ ★ 4,9/5

465 N McClurg Ct, 60611.0, Chicago

Boat tour agency

Why we chose them

Chicago River Boat Architecture Tours offers an exceptional opportunity to explore the architectural wonders of Chicago from the unique vantage point of the Chicago River. Known for its rich history and iconic skyline, Chicago is a city where architectural innovation thrives. The company provides an expert-led, in-depth riverboat tour that showcases over 50 significant buildings, highlighting designs, innovations, and the creators behind them. With guides who are architects, architecture students, or historians, these tours provide an engaging, educational experience that can’t be replicated through books or films.

In addition to the core architecture tours, the company offers a variety of themed experiences, such as the Chicago River Boat Cocktail Tour and Lake Michigan Navy Pier Fireworks Cruises. These options cater to diverse interests, allowing guests to enjoy cocktails or watch fireworks while absorbing the city’s architectural beauty. As proud Chicagoans, the team is committed to delivering entertaining, enlightening, and perfectly organized tours, ensuring visitors experience the city’s architectural grandeur firsthand. With daily tours available, they provide flexibility and convenience for anyone ready to explore the Windy City’s architectural treasures.

(312)9678687

3. Chicago Helicopter Experience

★ ★ ★ ★ ★ 4,8/5

1339 S Wood St, 60608.0, Chicago

Helicopter tour agency
Event venue
Helicopter charter
Sightseeing tour agency
Tour agency

Why we chose them

Chicago Helicopter Experience stands out as a premier helicopter tour agency, offering breathtaking aerial views of the iconic Chicago skyline. Known for its exceptional sightseeing tours, the company provides unforgettable experiences that highlight the city’s architectural marvels from a unique vantage point. As an established tour agency, it caters to both tourists and locals looking to explore Chicago in an exhilarating way. The personalized tours ensure that every passenger gains a new perspective on the Windy City’s beauty, making it a must-include in our directory.

In addition to scenic tours, the company excels as an event venue and helicopter charter service. This versatility allows clients to host memorable events with a backdrop of stunning aerial views or charter flights for bespoke travel needs. The company’s commitment to providing top-tier services in each of these areas demonstrates its dedication to customer satisfaction and innovation. This diverse range of offerings makes it a standout choice for those seeking exceptional aerial experiences in Chicago.

(312)5525100

4. Absolutely Chicago Segway Tours

★ ★ ★ ★ ★ 4,9/5

300 E Monroe St, 60603.0, Chicago

Sightseeing tour agency
Tour agency

Why we chose them

Absolutely Chicago Segway Tours offers an exceptional way to explore the Windy City, providing both visitors and locals with the opportunity to glide through Chicago’s most iconic sights. With guided tours covering 6-8 miles on a Segway or 8-13 miles on an e-Bike, participants experience landmarks from the stunning Lakefront to the historic Museum Campus. The tours are designed to be accessible and enjoyable, ensuring that if you can stand, you can Segway. For those preferring a different pace, the company’s eco-friendly electronic bike tours offer a smooth and effortless ride, making it a versatile option for diverse preferences.

The company boasts a variety of themed tours including the Chicago Insider Tour, Fireworks Tour, and Haunted Chicago: Ghosts & Gangsters Segway Tour. Each tour is designed to provide unique insights into Chicago’s rich history and vibrant culture. Whether it’s a private tour of Lincoln Park and the Gold Coast or a seasonal Holiday Lights Tour, participants are guaranteed a memorable experience. Conveniently located next to Millennium Park, the tours offer breathtaking views of Chicago’s lakefront, parks, and skyline, capturing memories through photographs and stories. This top-rated tour agency is renowned for its engaging and picturesque tours, making it a standout choice for anyone looking to explore Chicago in a fun and exhilarating way.

(312)9193367

5. Chicago Fireboat Tours

★ ★ ★ ★ ★ 4,9/5

111 N DuSable Lake Shore Dr, 60601.0, Chicago

Boat tour agency
Event venue

Why we chose them

Chicago Fireboat Tours, a veteran-owned and operated business, offers a unique way to explore the Windy City. Their flagship vessel, the historic Fred A. Busse, is a retired fireboat that served the Chicago Fire Department for 44 years. This vintage boat, built in 1936, provides an engaging setting for historical and architectural tours, cruises, and private charters on the Chicago River and Lake Michigan. Guests can enjoy panoramic views of the city’s skyline while learning about its rich maritime history and iconic architecture. The tours are family-friendly, with the exception of a 21+ Booze Cruise, and offer a relaxing experience for all ages.

The company stands out for its dedication to preserving history and providing an informative and enjoyable experience. Their expert tour guides share fascinating stories about the city’s architecture and the fireboat’s past, adding depth to the journey. The vessel itself is a testament to Chicago’s history, once the largest diesel-powered fireboat in the world. With a capacity of 127 passengers, the Fred A. Busse ensures a comfortable and spacious tour, unlike traditional crowded tour boats. Recognized for exemplary service, the company has won multiple Travelers’ Choice Awards on TripAdvisor, placing them in the top 10% of worldwide attractions for customer satisfaction.

(773)8811195

6. Untouchable Tour

★ ★ ★ ★ ★ 4,5/5

600 N Clark St, 60654.0, Chicago

Bus tour agency
Entertainment agency
Historical landmark
Sightseeing tour agency
Tour agency
Tourist attraction

Why we chose them

Untouchable Tour – Chicago’s Original Gangster Tour offers a unique and engaging way to explore the city’s notorious past. As a premier bus tour agency, they provide an immersive experience that transports guests back to the Prohibition era. Visitors can enjoy the comfort of a climate-controlled limo bus while guides, who take on the personas of 1920s gangsters, share thrilling stories of infamous figures like Al Capone and John Dillinger. The tour, which lasts between 1.5 to 2 hours, covers significant historical sites such as the St. Valentine’s Day Massacre location, the Biograph Theatre, and Holy Name Cathedral, making it a must-see historical landmark and sightseeing tour agency attraction in Chicago.

This entertainment agency is celebrated for its engaging and educational approach, offering prizes and interactive storytelling. Having worked with reputable media, including a feature on The Smithsonian Channel™, the tour is recognized as a top attraction. With over 35 years of experience, they have perfected the art of bringing Chicago’s gangster history to life, making it an unforgettable experience for tourists and locals alike. As a popular tourist attraction, advance reservations are recommended, ensuring that all guests have a “bang-up time” as they delve into the thrilling tales of Chicago’s criminal past.

(773)8317191

7. Windy City Ghosts

★ ★ ★ ★ ★ 4,8/5

2021 N Burling St, 60614.0, Chicago

Tour operator
Event planner
Event venue
Ghost town
Haunted house
Historical landmark
Sightseeing tour agency
Tour agency

Why we chose them

Windy City Ghosts offers a thrilling exploration of Chicago’s haunted past, engaging visitors with tales of the city’s rich history and supernatural occurrences. Known for its nightly ghost tours, the company takes guests on a spine-tingling journey through Chicago’s most notorious sites, including haunted bars, asylums, and infamous mobster hangouts. Participants can experience the eerie atmosphere of Lincoln Park, learn about the city’s violent history, and uncover stories of gangsters and bootleggers. With knowledgeable guides who bring these chilling tales to life, the company provides a unique blend of history, mystery, and excitement that captures the essence of the Windy City’s dark side.

The company’s services extend beyond ghost tours, offering event planning and venues at historical landmarks, making it a versatile choice for those interested in the supernatural and historical aspects of Chicago. The tours cater to a wide audience, ensuring both entertainment and education for all ages. Guests can expect to hear stories not found in history books, from tales of satanic rituals at the Golden Dagger to the spectral presence of notorious figures like Al Capone. This engaging narrative, combined with the expertise of local guides, creates an unforgettable experience that highlights why this company is a standout entry in our directory.

FAQs

What services do travel agencies in Chicago typically offer?

Travel agencies in Chicago typically offer services such as flight booking, accommodation reservations, custom travel packages, travel insurance, visa assistance, local tours and excursions, and transportation services.

How much do travel agency services cost in Chicago?

The cost of travel agency services in Chicago can vary widely depending on the services you need. On average, you might expect to pay between €50 and €200 for basic services such as flight booking and accommodation reservations. Customized packages and specialized services can range from €200 to €1000 or more.

How far in advance should I book through a travel agency for a trip?

It's generally recommended to book your trip through a travel agency at least 3 to 6 months in advance, especially for international travel or during peak holiday seasons, to ensure availability and get the best prices.

What should I look for when choosing a travel agency in Chicago?

When choosing a travel agency in Chicago, consider factors such as their reputation and reviews, experience and expertise, quality of customer service, range of services offered, pricing and value for money, and their ability to provide flexible and customizable options.

Do travel agencies in Chicago offer customized travel packages?

Yes, many travel agencies in Chicago offer customized travel packages that can include flights, accommodations, activities, and more, tailored to your preferences and budget.

Can travel agencies in Chicago help with visa applications?

Yes, many travel agencies in Chicago provide guidance and support for obtaining necessary travel visas, helping you navigate the application process.

Are there travel agencies in Chicago that specialize in specific types of travel?

Yes, some travel agencies in Chicago specialize in specific types of travel, such as luxury vacations, adventure travel, business trips, or family vacations, offering tailored services to meet those needs.

Is travel insurance necessary when booking through a travel agency?

While not mandatory, travel insurance is highly recommended when booking through a travel agency to protect against unexpected events such as trip cancellations, medical emergencies, or lost luggage.