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.
Partner of the Month: Silversea
Save up to $5,000 per Suite
For a limited time only, enjoy savings up to $5,000 per suite. Take advantage of this offer to journey farther on voyages worldwide, from iconic landmarks in the Mediterranean to Asia's hidden corners.
Reserve your suite by November 2, 2026 - with reduced deposits from 15%.
Best of the Danube
Join us for a Hosted Journey
Have you always wanted to experience a European river cruise? Join our President, Lynn Farrell on a special hosted journey aboard the beautiful Trafalgar Reverie as you sail the legendary Danube on May 29, 2027.
Additional Travel Deals
Celebrity Cruises
All Included
Drinks | Wi-Fi | $50 Savings
Celebrity Cruises allow you to wake up in a new place every day. One itinerary might trace Iceland's remote fjords, another Alaska's glacier-lined coast, while others drift through Japan's storied ports or the sun-drenched cities of Southern Europe. Every itinerary is an invitation to see a little more of the world and where it might take you next.
Trafalger River Cruises
Save up to 30% on your 2027 River Cruise
Trafalgar River Cruises promise spectacular stories, unforgettable flavors and rich connections both onboard and ashore, all in their award-winning style. When you plan ahead, you'll enjoy the widest choice of sailing dates and cabin categories, especially during the most sought-after travel periods, while giving yourself the flexibility to plan around your schedule.
Plus, save up to 30% on your 2027 river cruise when you reserve with us.