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
Royalton CHIC Punta Cana
Dominican Republic, Caribbean

Luxury and Leisure: Royalton CHIC Punta Cana Plus Airfare from Chicago O'Hare!

3-7 Nights + Nonstop Airfare from ORD

Starting from $529

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $529

per person
Packages
Paradisus Palma Real Resort
Dominican Republic, Caribbean

Palma Perfection: Jet Set from Chicago O'Hare to Paradisus Palma Real Resort!

3-7 Nights + Nonstop Airfare from ORD

Starting from $879

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $879

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
Melia Punta Cana Beach Resort
Dominican Republic, Caribbean

Punta Cana Perfection: Meliá Punta Cana Beach Resort Bliss Awaits from Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $739

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $739

per person
Packages
Melia Caribe Beach Resort
Dominican Republic, Caribbean

Caribe Escape: Fly Direct from Chicago to Meliá Caribe Beach Resort!

3-7 Nights + Nonstop Airfare from ORD

Starting from $689

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $689

per person
Packages
Secrets Tides Punta Cana
Dominican Republic, Caribbean

Beachfront Bliss: Adult Retreat at Secrets Tides Punta Cana from Chicago O'Hare!

4-7 Nights + Nonstop Airfare from ORD

Starting from $1,129

per person

4-7 Nights + Nonstop Airfare from ORD

Starting from $1,129

per person
Packages
RIU Latino
Costa Mujeres, Mexico

Latino Luxe: Discover RIU Latino with Direct Flights from Chicago!

3-10 Nights + Nonstop Airfare from ORD

Starting from $549

per person

3-10 Nights + Nonstop Airfare from ORD

Starting from $549

per person