Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Diego, California: Econ from $151.- Dec-Feb (Including MLK Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Montego Bay, Jamaica: Biz from $513 Econ from $276.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cartagena, Colombia: Biz from $625 Econ from $247. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Leon, Mexico: Biz from $652. Econ from $264. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Diego, California: Econ from $122.- Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Belize City, Belize: Biz from $640. Econ from $303. – Dec-Feb
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Cozumel, Mexico: Biz from $1003 Econ from $246.- Feb-Apr
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Colombo, Sri Lanka: Econ from $735. – Mar-May (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Prague, Czech Republic: Econ from $447. – Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Bangkok, Thailand: Econ from $682. – Jan-Mar
* This is a “fare dump” with a few alternate dates available.
ORD > Coxen Hole, Honduras: Biz from $1424. Econ from $489. – Nov-Jan
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Thera, Greece: Econ from $674. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubai, United Arab Emirates: Econ from $589. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Hamburg, Germany: Econ from $515. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > George Town, Cayman Islands: Biz from $660 Econ from $305. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Belgrade, Serbia: Econ from $485. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Algiers, Algeria: Econ from $553.- Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Colombo, Sri Lanka: Econ from $774. – Mar-May (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Barcelona, Spain: Econ from $356. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kuala Lumpur, Malaysia: Econ from $649.- Jan-Mar (Presidents day Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Tunis, Tunisia: Econ from $568. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Luqa, Malta: Econ from $544. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Casablanca, Morocco: Econ from $539.- Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Belize City, Belize: Econ from $363. – Dec-Feb (Including Winter Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Florianopolis, Brazil: Biz from $2924 Econ from $725. – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Kos, Greece: Econ from $667. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Belgrade, Serbia: Econ from $504. – Mar-May (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Berlin, Germany: Econ from $439. – Oct-Dec (Including Thanksgiving)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dhaka, Bangladesh: Econ from $780. – Nov-Jan (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Rabat, Morocco: Econ from $529. – Nov-Jan (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Hong Kong, Hong Kong: Econ from $710. – Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Funchal, Portugal: Econ from $470. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cluj Napoca, Romania: Econ from $486. – Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Algiers, Algeria: Econ from $539. – Nov-Jan (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Colombo, Sri Lanka: Econ from $733. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Dubai, United Arab Emirates: Econ from $741. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dublin, Ireland: Econ from $374. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Abuja, Nigeria: Biz from $3217. Econ from $790. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…