Americas – Short Flights, Big Adventures
Just a hop skip away… Coast to coast, mountain top to valley floor, North and South America have something to offer even the most discerning traveler.
If action and adventure is your cup of tea, try skiing the snow topped mountains of Whistler or Aspen. Prefer a warmer climate? Zip-line your way across Costa Rica or snorkel the cenotes of Mexico. If you prefer a more tranquil experience, hit the beaches of Baja or Riviera Maya and let the fruity drinks flow under your breezy cabana. For a tropical adventure, explore the jungles and rainforests in Brazil or visit the historic Incan ruins in Peru.
Quite simply, America has it all.
Easy Travel & Big Savings – Shorter flights (often direct) means you don’t spend a good portion of your trip sitting on a plane. That shorter flight can also shave big bucks off your trip, leaving you more to spend on exploring your destination.
All Inclusive – From Mexico down through Central America, many of the resorts are all inclusive. Not only does this save some money, it means you don’t have to spend your time trying to make reservations or getting to and from restaurants. Did we mention your drinks are included too? Yeah, they are.
Great for Groups – While Windy City Travel can make booking your group travel a breeze regardless where you decide to go, sometimes it’s easier for the members of your group to schedule travel that isn’t so far away.
Weekend Getaways – While you’re not taking a 3 day trip to Fiji, you can surely do so in Puerto Vallarta!
Our agents have extensive knowledge about the resorts, culture, activities, and dining that will make your North or South American adventure one you’ll never forget.
Featured North American Journeys
Christmas In August 2022
Save up to $300
Holiday cheer comes early this year. Take advantage of these savings to treat yourself to the gift of travel. Plan a romantic getaway this year or next.
Save up to $300 Instantly (per room, …more
Book By:
Travel: August 1 – December 23, 2023 Minimum Nights: 5 Promo Code: N/A |
10 Night Hawaii Cruise from $799 From $799
Book By: Saturday October 30th, 2021
Travel: April 25 – May 5, 2022 Minimum Nights: 10 Promo Code: N/A |
Better by the Beach
Save up to 75% + Free Extras
Save Up to 75% + Free Extras
Grab your swimsuit and flip flops and h…more
Book By: Thursday April 29th, 2021
Travel: April 2 – December 15, 2021 Minimum Nights: 3 Promo Code: N/A |
Featured South/Central America Journeys
Royal Caribbean’s Rise to the Vacation
Save up to 30% Off & More
Book By: Sunday January 2nd, 2022
Travel: January 1 – December 31, 2024 Minimum Nights: 4 Promo Code: N/A |
Better by the Beach
Save up to 75% + Free Extras
Save Up to 75% + Free Extras
Grab your swimsuit and flip flops and h…more
Book By: Thursday April 29th, 2021
Travel: April 2 – December 15, 2021 Minimum Nights: 3 Promo Code: N/A |
Funjet Mystery Deals
Save up to 40%
You pick the destination, we pick the resort.
It’s that simple.
Here’s how the magic happens:
• We wil…more
Book By:
Travel: April 3 – August 29, 2022 Minimum Nights: 3 Promo Code: N/A |
Start Planning Your American Journey
Call us at (312) 951-0710 or fill out the short form below to start planning your next experience.
