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.

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 $749

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $749

per person
Packages
Dreams Cap Cana Resort & Spa
Dominican Republic, Caribbean

Cap Cana Dreaming: Escapes to Dreams Cap Cana Resort from Chicago!

3-7 Nights + Nonstop Airfare from ORD

Starting from $659

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $659

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 $1,119

per person

7 Day Guided Tour

Starting from $1,119

per person
Packages
Hyatt Vivid Grand Island
Cancun, Mexico

Discover Paradise: Ocean Serenity at Hyatt Vivid Grand Island from Chicago!

3-8 Nights + Nonstop Airfare from ORD

Starting from $749

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $749

per person
Packages
6 Days in Grand Teton
Jackson, Wyoming

Experience the wonders of Grand Teton & Jackson Hole

5 Nights + Nonstop Airfare + Rental Car

Starting from $1,729

per person

5 Nights + Nonstop Airfare + Rental Car

Starting from $1,729

per person
Packages
Paris City Getaway
Paris, France

Paris Getaway: 6 Nights at Hotel Beauregard with Nonstop Airfare for $1,338 per person!

6 Nights + Nonstop Airfare + Transfers

Starting from $1,338

per person

6 Nights + Nonstop Airfare + Transfers

Starting from $1,338

per person
Guided TourEXCLUSIVE
Explore Scotland with Tom Kief – SOLD OUT
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
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 $679

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $679

per person
Packages
Dreams Tulum Resort & Spa
Tulum, Mexico

Tulum Tranquility: All-Inclusive at Dreams Tulum Resort & Spa from Chicago O'Hare!

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
Dreams Vista Cancun Golf & Spa Resort
Cancun, Mexico

Cancun Panorama: Experience Dreams Vista Cancun Golf & Spa Resort from Chicago!

3-8 Nights + Nonstop Airfare from ORD

Starting from $629

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $629

per person