Featured Travel Deals

All Travel Deals

Vacation Types
20 Deals
TitleDestination(s)Min NightsPrice FromDiscountSupplierTypesPromo CodeExpiresLink
Mexico’s Caribbean Coast w/ Apple
Mexico’s Caribbean Coast w/ AppleCaribbean, Mexico3$549Apple VacationsLand VacationThursday February 27th, 2020
Secrets - Unlimited Luxury
Secrets – Unlimited LuxuryBahamas, Caribbean, Central America, Mexico, South America3$859Apple VacationsLand VacationThursday April 30th, 2020
1/2 Off Marival Resorts
1/2 Off Marival ResortsMexico353%Funjet VacationsLand VacationTuesday December 15th, 2020
iceland vacations
2020 A&K Cruises – An Unbelievable JourneyArctic, Europe, North America15$6,000Abercrombie & KentCruise, River Cruise, Sea CruiseFriday March 20th, 2020
Great Lakes & Canada w/ Viking
Great Lakes & Canada w/ VikingNorth America7$5,995Viking CruisesCruise, River Cruise, Sea CruiseSaturday February 29th, 2020
holland america verandah
View & Verandah – Free Upgrades and MoreAsia, Australia / New Zealand, Caribbean, Europe, Hawaii4$399Holland America LineCruise, Sea CruiseFriday February 28th, 2020
China & the Yangtze Small Group Journey
China & the Yangtze Small Group JourneyAsia12$6,395Abercrombie & KentCruise, Land Vacation, River CruiseThursday April 30th, 2020
South Africa Explorer
South Africa ExplorerAfrica9$1,000 Per CoupleAfrica Travel Inc.Land VacationTuesday March 31st, 2020
Spain & Portugal: A Journey Across Iberia 2020
Spain & Portugal: A Journey Across Iberia 2020Europe14$10,895Abercrombie & KentLand VacationFriday May 1st, 2020
Winter Vacation Deals to AMResorts
Winter Vacation Deals to AMResortsCaribbean, Mexico340%Apple VacationsLand VacationTuesday February 25th, 2020
Explore Europe's Christmas Markets with AmaWaterways
Explore Europe’s Christmas Markets with AmaWaterwaysEurope7$1,000 Per PersonAmaWaterwaysCruise, River CruiseWAVE-EURMonday March 30th, 2020
African Safari Vacations
African Safari VacationsAfrica8$3,789GlobusLand VacationTuesday April 28th, 2020
Sail Into Adventure
Sail Into AdventureCentral America7$800Un-CruiseCruise, River Cruise, Sea Cruise800LAM20Friday February 28th, 2020
backroads costa rica
Costa Rica Multi-Adventure Tour by BackroadsSouth America5$4,099BackroadsLand VacationSunday March 22nd, 2020
france spain vacation
Backroads French Basque Country Walking & Hiking TourEurope5$3,799BackroadsLand VacationSaturday February 22nd, 2020
Thailand and Laos Adventure
Thailand and Laos AdventureAsia13$1,359SignetLand VacationMonday March 16th, 2020
Atlantis The Palm Dubai
Luxury in DubaiMiddle East2$330Classic VacationsLand VacationTuesday March 31st, 2020
kenyas samburu masai mara x450
Kenya’s Samburu & Masai MaraAfrica7$3,195SignetLand VacationSunday March 22nd, 2020
Waikiki Explorer
Waikiki ExplorerHawaii4$695SignetLand VacationSaturday March 28th, 2020
Tropical WonderAustralia / New Zealand4$964SignetLand VacationWednesday March 18th, 2020

These are some of the best deals currently available. Not sure where to go or what to do? Give us a call, we're here to help!

Why book with Windy City Travel?
  • We’ll save you time & money
  • We’ve been to the destinations & stayed at the resorts
  • Easy & stress free booking
  • We’re your advocate before, during, & after your trip

Call now & save. We’re here to help!


Travel Planning

  • This field is for validation purposes and should be left unchanged.

Our travel specialists have stayed at or visited most of the vacations we recommend (unlike most online agencies). In order to best match your requirements with the array of resorts, packages and options available, we believe it is best for us to speak with you personally by phone about your vacation.

If you can’t call us now or our office is currently closed, please schedule a personal free one on one consultation below with one of our travel specialists when it is convenient for you and let us take all the stress out of planning your vacation. Thank you for considering Windy City Travel!

Lynn Farrell
(312) 951-0710