Travel Deals

Featured Travel Deals

Windy City Travel periodically offers travel deals in partnership with our travel providers. Please check out some of our featured offers at the links below. Feel free to contact us with any questions.

Take Off with Tauck

Once the summertime travel season winds down, European landscapes come alive with autumn harvests, fall festivals, fabulous foliage and mild temperatures perfect for taking it all in – with fewer crowds and more opportunities to experience their cultural treasures.

Ask about air savings on 2024 European tours and cruises departing in October and November.

Discover Africa's Best-Kept Secret — the Green Season.

Characterized by lush landscapes and abundant wildlife, this season typically spans from November to May in East Africa. With fewer tourists and special offers, such as extra free nights, the Green Season provides travelers with the opportunity to experience Africa's natural beauty in a more intimate setting and at a slower pace. Enjoy an extra night in select properties.

Book starting June 1st to extend your safari and create timeless memories in Africa's most iconic destinations!

Save at the Grand Wailea

Discover a retreat shaped by nature and defined by culture at Grand Wailea. The recently enhanced oceanfront resort features 40 acres of lush tropical landscape, luxurious accommodations, a new spa and wellness destination, Kilolani Spa, and exceptional culinary experiences such as an award-winning signature seafood restaurant, Humuhumunukunukuapua'a, and Olivine, a fine dining venue offering coastal Italian cuisine.

Enjoy a $150 Kilolani Spa credit and a guaranteed single category upgrade at the time of booking.

Complimentary Land Package

Relax on San Sebastian’s sparkling shores. Take in the landscapes that inspired artists in the French Riviera. Extend your stay in Amsterdam before embarking on your river cruise journey. All of these experiences can be yours – courtesy of AmaWaterways. Explore an incredible city where your river cruise begins or ends – or venture into a fascinating new destination more easily accessible by land.

For a limited time, new reservations receive a complimentary 2-, 3-, or 4-night land package before or after select 2024 and 2025 Europe river cruises.

Additional Travel Deals

Land Vacations


Hot Offers