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
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 $579

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $579

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

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

3-7 Nights + Nonstop Airfare from ORD

Starting from $749

per person

3-7 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 $599

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $599

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
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
RIU Palace Riviera Maya
Riviera Maya, Mexico

Royal Getaway: Experience the Grandeur of RIU Palace Riviera Maya from ORD!

3-7 Nights + Nonstop Airfare from ORD

Starting from $549

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $549

per person
Packages
Grand Oasis Cancun
Cancun, Mexico

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

3-8 Nights + Nonstop Airfare from ORD

Starting from $549

per person

3-8 Nights + Nonstop Airfare from ORD

Starting from $549

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 $699

per person

3-7 Nights + Nonstop Airfare from ORD

Starting from $699

per person
Packages
RIU Palace Macao
Dominican Republic, Caribbean

Palm-Lined Perfection: Escape to RIU Palace Macao with Air 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