Whether it’s negative seven degrees or you have vacation days stashed away, planning your escape begins with Windy City Travel’s knowledgeable consultants. Too many choices? No problem, we have not only traveled the world for you, but have lived abroad as well. Our firsthand location knowledge and experience are only an email or call away. Packing, yet?

Romantic Vacations and Getaways

Romantic Getaways

Explore secluded beaches and unknown hideaways. Relax in a Balinese spa. Swim at midnight in your plunge pool, hang on a private hammock, and have champagne for breakfast.

Adventure Getaway

Swim with dolphins and stingrays, feed sharks, zip line through a jungle, surf in Maui or Costa Rica, Ride through the dunes on an All-terrain vehicle (ATV), balloon over the Serengeti, Hop on an elephant and ride during sunset, or taste the local cuisine from a street vendor in Bangkok.
Adventure Travel and Vactions
Family Vacation

Family Getaway

Share a six scoop ice cream cone in the Bahamas, send the kids to trapeze school while you reach for your second margarita, horse back ride through the waterfalls of Costa Rica or stop for a picnic on Aruba’s crystal clear ocean. Be guests at an authentic Hawaiian Luau or experience the climbs to the top of some ancient Mayan ruins.

Golf Getaway

Travel in style and still get your rounds in. Whether you're looking to tee off in the Caribbean sun or in the homeland of Ireland, we'll help you find that perfect destination and resort to ensure your time off the course is a great as your time on.
Golf Vacation
(312) 951-0710
Vacation Request
LGBT Vacations

LGBT Getaways

Dreaming of the ultimate vacation with your special someone in a gay-friendly destination? Want to make new friends in a safe and welcoming environment? Windy City Travel can help with gay friendly vacations tailored to gay and lesbian travel. Travel confidently and mingle with people of like mind and spirit in some of the most beautiful destinations in the world while saving money with our amazing vacation packages.

Adults Only Getaways

Escape on enchanting adults only vacations in the world's most celebrated tropical destinations. Windy City Travel brings the most remarkable adults only, all inclusive resorts in the Caribbean, Central America, and Mexico to your feet. If your visions of paradise involve a romantic beach holiday - minus kids - that plays to the soundtrack of ocean waves, exotic birds, and swaying palm trees, at Windy City Travel, we can make your vacation dreams come true!
Adults Only Vacation
Singles Vacations

Singles Getaways

If you’re travelling solo and are looking for a fun-filled and affordable vacation, Windy City Travel can help with our amazing singles vacations. Whether you’re looking to de-stress and relax, get active with some exciting adventures, learn about a new culture and explore a new country, or mingle with other travelers to make new friends, our single holidays can help you design the vacation you’re looking for.

Spring Break

Whether your on college spring break or looking to pack up your family and the little ones, Windy City Travel has your spring break covered! If you're looking to party til' the sun comes up or a quiet getaway for a week, the options are endless and Windy City will find the perfect resort for you!
Spring Break Beach Vacation
(312) 951-0710
Vacation Request