Group Travel

Group Travel - Share Your Journey

See what the Windy City Travel Experience is all about with our experienced & dedicated group travel agents.

  • Free Upgrades

    By booking your group travel together, you can take advantage of free room upgrades, rooms close together in the hotel, group dinner reservations, excursions in your destination, and more.

  • Group Discounts

    Free rooms, free flights, and more! When you book your group together, you save! From initial travel to excursions in your destination, added value is everywhere when you travel in a group.

  • 5-Star Customer Service

    By booking with a real travel agent instead of an online only agency, you get the assistance and support of an actual agent that has been to the resort and knows the area. Your group vacation will only benefit from the customer service provided by an agency like Windy City Travel!

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Group Travel for ANY Occasion

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Family & Social

Want to take a family or friends trip and reap the benefits of group travel? Pile up the suitcases for winter break, spring break, or just a short weekend getaway. Swim with dolphins or float along an underground river in a Mayan ecological park. Zip line above a winding river that ends at a jungle bar. Dine together with international fare to fit everyone's taste. Let Windy City Travel take the stress out of planning a perfect family or social getaway for you and yours.

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Business & Corporate

An effective way to motivate a workforce is rewarding top achievers with a trip of a lifetime. At Windy City Travel, we can help design an incentive program that is bound to create results.


We can design a high-quality, cost-effective program that will impress and encourage everyone involved. Windy City Travel's detailed and thorough approach is only a phone call or e-mail away.

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Destination Weddings

Getting married? Destination weddings are a great option, and we can help you find the right destination for your perfect wedding. While traditional weddings can be expensive, destination weddings can be surprisingly affordable. They also extend your dream day into a beautiful and enjoyable mini-vacation for both you and your guests. Let us arrange a unique, memorable destination wedding to ensure you enjoy your once in a lifetime celebration.

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Take in the sights abroad with your school, church, or community organization and see how much easier it is to bond and grow when you share amazing experiences together. On sea or land, our group specialists will ensure that every detail is taken care of so that everyone in your group will enjoy. Call us today and see why Windy City Travel is Chicago's leader in group travel experts.

Start Planning Your Group Journey

Call us at (312) 951-0710 or fill out the short form below to start planning your next experience.

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