Nonstop Vacations out of

Chicago

Chicago Travel Deals

Nonstop to Paradise!

Ready to head out of the windy city for some worldly adventures? We are too. Below you’ll find some of the best deals of Chicago O’Hare and Chicago Midway International Airport.

Chicago Travel Deals

Nonstop to Paradise!

Ready to head out of the windy city for some worldly adventures? We are too. Below you’ll find some of the best deals of Chicago O’Hare and Chicago Midway International Airport.

Guided TourEXCLUSIVE
Explore Scotland with Tom Kief
Globus
Join Tom Kief from 95 Will Rock and LaMacchia Travel this May 2025 and discover the highlights of the Scottish land!

Air + First Class Tour

Starting at $4,199

per person

Air + First Class Tour

Starting at $4,199

per person
Packages
Secrets The Vine Cancun
Cancun, Mexico

Luxury Awaits in Cancun: Secrets The Vine + Direct Chicago O'Hare Flights!

3-8 Nights + Nonstop Airfare from ORD

Starting from $969

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $969

per person
Packages
Secrets Riviera Cancun Resort & Spa
Riviera Maya, Mexico

Riviera Rendezvous: Luxury Getaway at Secrets Riviera Cancun from Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $1,099

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $1,099

per person
Guided Tour
Costa Rica Escape
Globus
Costa Rica Uncovered: A 7-Day Guided Escape Through Monteverde Cloud Forests, Arenal Volcano, and San José's Vibrant Heart!

7 Day Guided Tour

Starting from $1,199

per person

7 Day Guided Tour

Starting from $1,199

per person
Packages
Iberostar Waves Paraiso Beach
Playa Del Carmen, Mexico

Waves of Luxury: Escape to Iberostar Waves Paraiso Beach from Chicago!

3-8 Nights + Nonstop Airfare from ORD

Starting from $669

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $669

per person
Packages
Secrets Tulum Resort & Beach Club
Tulum, Mexico

Tulum Temptations: Jet from Chicago to Sun, Sand & Secrets Tulum Resort & Beach Club!

3-8 Nights + Nonstop Airfare from ORD

Starting from $869

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $869

per person
Packages
JOIA Paraiso by Iberostar
Playa Del Carmen, Mexico

Paradise Found: Uncover Luxurious Tranquility at JOIA Paraiso with Direct Flights from ORD!

3-8 Nights + Nonstop Airfare from ORD

Starting from $969

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $969

per person
Packages
JOIA Bavaro by Iberostar
Dominican Republic, Caribbean

Bavaro Elegance: Chic Retreat to JOIA Bavaro by Iberostar from Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $999

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $999

per person