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Vacations 2017-06-23T09:08:44+00:00


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.
Romantic Vacation Request

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 Vacation Request
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.
Family Vacation Request

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 Request
Golf Vacation
Call (312) 951-0710
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.
LGBT Vacation Request

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!
Adult Vacation Request
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.
Singles Vacation Request

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 Vacation Request
Spring Break Beach Vacation
Call (312) 951-0710

TERMS AND CONDITIONS: Prices per person based on double occupancy (unless otherwise stated) including round-trip airfare via U.S. certified air carriers, round-trip airport/hotel transfers, hotel taxes and baggage handling, fuel surcharges, all pre-collected U.S. and foreign taxes and fees including September 11th Security Fee, $10 late booking fee if applicable (for bookings within 14 days of departure). Packages to Hawaii and Europe do not include airport transfers. Packages in Turks and Caicos or San Juan, Puerto Rico do not include airport transfers. Packages flying into Cancun but staying in Cozumel require supplemental ferry transfers at an additional cost. In some instances, pricing may specifically apply to one of multiple flights on select departure days. All packages are based on the lowest hotel/air classes available at time of publication, capacity controlled, subject to availability and may change without notice. Promotional pricing may only be available for a limited time. Holiday/weekend surcharges may apply. Restrictions/blackout dates may apply. Where Kids, Stay, Play and Eat Free, Kids pay regular airfare including taxes. Checked bag fees from the air carrier may apply, ranging from $10-$100 per bag. The following fees are subject to change: resort fees for hotels in Hawaii may apply and range from $10-$30 per room, per night payable directly to the hotel; $10 Dominican Republic Tourist Card fee payable at resort airport upon arrival-cash only, U.S. dollars; $29 Costa Rica Departure tax payable at resort airport upon departure-U.S. dollars, colones, Visa or MasterCard are accepted. Traveloni is not responsible for errors or omissions. Vacation Supplier cancellation policies apply.


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