Travel Deals

Partner of the Month

Each month we feature an exclusive offer from one of our valuable partners.

30% off Every Cruise plus Kids Sail FREE plus up to $150 off

Take your family to the most captivating corners of the globe with big savings on your next adventure. Whether you go roaming past soaring steeples and historical highlights in Paris, take in the majesty Alaska’s untamed wilderness, or hike through dense rainforests to unearth hidden temples in the heart of Cozumel, the experiences will give you and your family memories you’ll want to share over and over again.

ENJOY MASSIVE SAVINGS: Up to $150 off sailings departing October 5, 2023 or after.
BRING THE WHOLE CREW: Save 30% off every guest.
AIRFARE LOVE: Up to $500 off air bookings for sailings departing between October 1 – 31, 2024.
KIDS SAIL FREE: Little adventurers sail free of charge*.

EXCLUSIVE OFFER FOR OUR CLIENTS:
Book a Balcony or Suite and receive a specialty dining experience for two*.

*Click below for specific terms and conditions.

Terms & Conditions

Featured Travel Deals

Windy City Travel periodically offers travel deals in partnership with our travel providers. Please check back often for the latest deals and offers.

AmaWaterways Supports Maui

$100 donation made on your behalf

“Ama” means love – and we believe that love should be shared with those who need it the most, including our beloved guests and their loved ones who are rebuilding their lives in Maui. With this in mind, we are proud to announce that, when you reserve and place a deposit on your river cruise between September 11 and October 15, 2023, AmaWaterways will make a charitable $100 donation to the Travel Elevates Fundraiser HCF (Hawai’i Community Foundation) – because travel is a force of good in the world and we believe in the importance of supporting our global community.

8-Nights Greek Cyclades

Exclusive Deal from $1,975

Discover the historical treasures of the Acropolis in Athens, then, travel by train to Kalambaka and join a excursion to hike to the Monasteries of Meteora for a truly unique experience. Then, spend a few days lounging on the pristine beaches of Syros and Paros in the heart of the Cycladic islands.

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Windstar Cruises

Up to $1,000 per Cabin Shipboard Credit in Select Categories

Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.

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