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 Riviera Cancun
Riviera Maya, Mexico

Riviera Rapture: Luxe Escape at Royalton Riviera Cancun from Chicago O'Hare!

3-9 Nights + Nonstop Airfare from ORD

Starting from $669

per person

3-9 Nights + Nonstop Airfare from ORD

Starting from $669

per person
Packages
Dreams Onyx Resort & Spa
Dominican Republic, Caribbean

Onyx Elegance: Discover Ultimate Luxury at Dreams Onyx Resort & Spa from Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $799

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $799

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 $659

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $659

per person
Packages
Grand Oasis Cancun
Cancun, Mexico

Cancun Carnival: Grand Oasis Cancun Awaits with Direct Flights from Chicago!

3-9 Nights + Nonstop Airfare from ORD

Starting from $599

per person

3-9 Nights + Nonstop Airfare from ORD

Starting from $599

per person
Packages
Breathless Punta Cana Resort & Spa
Dominican Republic, Caribbean

Punta Cana Pulse: Experience the Excitement at Breathless Resort from Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $949

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $949

per person
Packages
Hyatt Ziva Riviera Cancun
Riviera Maya, Mexico

Escape to Elegance: Luxury at the Hyatt Ziva Riviera Cancun from Chicago O'Hare!

3-7 Nights + Nonstop Airfare from ORD

Starting from $729

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $729

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 $1,159

per person

7 Day Guided Tour

Starting from $1,159

per person
Packages
Ocean Blue & Sand
Dominican Republic, Caribbean

Sapphire Shores: Luxurious Getaways to Ocean Blue & Sand from ORD!

3-7 Nights + Nonstop Airfare from ORD

Starting from $649

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $649

per person
Packages
Ocean El Faro
Dominican Republic, Caribbean

Lighthouse Luxury: Experience Ocean El Faro's Unmatched Elegance From Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $669

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $669

per person