7 best travel agencies in Chicago

Anyone can go online and make a reservation, but when you want to plan a truly memorable trip, travel agents are the experts you turn to for personalized experiences and insider knowledge that make all the difference.

Whether you want to safari in Africa, snorkel in Hawaii, or sip an Aperol in Italy, travel agencies are ready to advise you on vacation packages, itineraries, and more. Or, if you’re in charge of booking independent travel for employees, business travel agencies can help you manage every aspect of the trip.

If you’re based in the Windy City and are looking for the lowdown on the best travel agencies in Chicago, look no further.

Best travel agency in Chicago for business travel

1. TravelPerk

TravelPerk is a corporate travel management company that offers an all-in-one digital platform. Our state-of-the-art travel management solution helps you organize all aspects of your company’s business trips. Using the platform, employees can book and manage their own corporate travel.

You’ll have access to a massive travel inventory for flights and accommodation, and a huge catalog of integrations with third-party software at your fingertips. Trains, planes, cars, or anything else you might fancy—we offer a wide variety of booking options to suit all your travel needs.

Our corporate travel solution comes with many useful features, such as:

24/7 dedicated human business travel assistance with a target 15-second response rate.

The FlexiPerk functionality, which lets your employees cancel their business trip arrangements up to two hours before departure, with a guaranteed refund of 80%.

Peace of mind with TravelCare, a safety and travel alert system that is comprehensive and up-to-date.

Built-in automated travel policies and an in-app approval system that includes approval workflows. You can save trip details for later, and customize the level of strictness for each workflow.

Extensive reporting capabilities and expense dashboards to help you manage a simplified travel expense process.

The GreenPerk carbon offsetting program, which makes it easy for your company to report on carbon control initiatives.

G2 rating: 4.6 / 5 stars, based on 1,533 reviews

Capterra rating: 4.7 / 5 stars, based on 404 reviews

See how to save your company time and money on business travel.

Best travel agencies in Chicago for leisure travel

2. Windy City Travel

If you’re looking for a full-service travel agency specializing in vacations, destination weddings, and honeymoons, look no further than Windy City Travel. In business for over four decades, their specialist travel advisors customize every aspect of your trip to align with your travel needs. Count on their expertise and recommendations to design getaways and itineraries of your dreams.

From a family break in the Bahamas, spring break in the Dominican Republic, or a river cruise holiday in India, the company’s list of destinations is endless.

Windy City Travel promises 5-star service and prides itself on the fact that two-thirds of its business comes from repeat or referral customers.

Windy City Travel’s main offerings include:

Group travel support

Free perks and upgrades

Personal, one-on-one service

Group dinner reservations

Land and cruise vacations

3. Cerulean World Travel

Chicago-based Cerulean World Travel is a luxury travel agency that “doesn’t believe in mediocre vacations”. Its team of travel specialists delivers personalized recommendations to help create the travel experiences of your dreams.

The agency specializes in creating global travel plans for leisure travelers, including family vacations, honeymoons, LGBTQ travel, and experiential travel experiences. It also offers some niche travel planning options, including life travel planning, multigenerational travel, and gratitude travel.

Whether you’re interested in a European road trip or a remote luxury fishing lodge in Alaska, Cerulean World Travel can help you plan a trip to remember.

Some of Cerulean World Travel’s services and features include:

Itinerary planning

Trip planning to a wide variety of global travel destinations

Cruise, safari, and island travel options

4. Sunset Travel

Located in Chicago’s Lincoln Park neighborhood, Sunset Travel is a travel and cruise agency that’s been in the vacation business since 1973.

The company specializes in crafting vacations, securing insider deals and flight discounts, and exclusive packages. Whether you’re thinking of resorts, tours, group vacations, or destination weddings, Sunset Travel’s team of travel agents, advisors, planners, concierges, and consultants are focused on creating the best travel experiences for their clients.

The company partners with a vast network of travel suppliers to create customized, one-of-a-kind vacations and will take care of booking flights, accommodation, transportation, excursions, and tours.

Some of Sunset Travel’s features and services include:

Resort and hotel packages

Ground transportation

Exclusive, local tours

Museums, exhibits, and show tickets

Restaurant recommendations and reservations

5. Vega

Based in the heart of Chicago, Illinois, travel agency Vega has been in the business of worldwide travel planning for over 75 years. The company describes itself as a dynamic travel planner and booking agent and its advisors are experts in both business and leisure travel.

However, Vega’s expertise is clear when it comes to luxury leisure travel planning. The company is a preferred partner agency with Ritz Stars, Hyatt Privé, Belmond Bellini Club, Jumeirah Passport to Luxury, and Shangri-La’s The Luxury Circle where guests receive VIP access, complimentary breakfast, and room upgrades.

Plus, the company also specializes in cruise holidays, yacht, and villa booking, and will single-handedly organize events, surprise trips, weddings, and anniversaries.

Finally, if you’re looking for a truly bespoke event or trip, Vega can help. Just some of the unique trips they’ve organized include a private balloon flight over the Loire Valley in France, the real Harry Potter bookshop surprise event in Portugal, and a Polynesian-style vow renewal in Bora Bora.

Vega’s other travel services include:

Local partners that can provide special access to popular destinations

Creative events team

Family travel vacations

Passport renewals

Air mile advisors

6. Chambers Travel

Unlike your average travel agency, Chambers Travel is an agency with a twist. It’s a full-service agency that’s run by Sabrina Chambers, a certified travel agent who has over 12 years of experience in designing custom vacation packages.

If you want a true, one-on-one service, you can work directly with Sabrina to design a customized vacation package, destination wedding, reunion, or group travel booking.

Chambers Travel can help you:

Find the best deals on flights, hotels, and car rentals

Discover all-inclusive package deals

Travel to a range of destinations including Jamaica, Puerto Rico, and Bermuda

7. Venus Travel

Founded in 1968, Venus Travel offers corporate, leisure, domestic, and international travel plans tailored to businesses or individual budgets and interests.

Whether you’re traveling to Manhattan or Mexico, they’re experts in creating vacation packages across the USA, Central and South America, Europe, Asia, and Australia.

Venus Travel services include:

Partnerships with airlines, hotels, and travel resources to secure the best rates

Travel events and services

Group travel

Take travel planning off your plate with one of the best travel agencies in Chicago

Whether you’re looking for an all-inclusive vacation package or a custom-built itinerary, this list of the best travel agencies in Chicago has you covered.

Or, if your employees are traveling for business, TravelPerk can help you book and manage all your travel arrangements while also helping you reduce costs, manage your expenses, and access flexible booking options. Reach out today to see how TravelPerk can help streamline your business travel management program!