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 $610 Econ from $298.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Krakow, Poland: Econ from $389.- Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Gdansk, Poland: Econ from $495. – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Guatemala City, Guatemala: Biz from $436. Econ from $218. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Tunis, Tunisia: Econ from $568. – Nov-Jan [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Abu Dhabi, United Arab Emirates: Econ from $764. – Feb-Apr
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 [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $275. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dallas, Texas: Biz from $226 Econ from $53.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Poznan, Poland: Econ from $492.- Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Riga, Latvia: Econ from $415.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Diego, California: Econ from $103.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Fort Lauderdale, Florida: Biz from $295 Econ from $66.- Nov-Jan [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
MDW > Casablanca, Morocco: Econ from $539.- Nov-Jan [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Madrid, Spain: Econ from $323.- Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Almaty, Kazakhstan: Econ from $821.- Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Dublin, Ireland: Econ from $345.- Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: Econ from $444.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Pedro Sula, Honduras: Biz from $489 Econ from $243.- Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Athens, Greece: Econ from $492. – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belize City, Belize: Econ from $363. – Dec-Feb (Including Winter Break) [SOLD OUT]
* 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 [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Hamburg, Germany: Econ from $467. – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Tbilisi, Georgia: Econ from $561. – Nov-Jan [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cairns, Australia: Econ from $1088. – Nov-Jan [SOLD OUT]
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 [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > George Town, Cayman Islands: Biz from $463. Econ from $271. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Bucharest, Romania: Econ from $489. – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Male, Maldives: Econ from $950. – 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…
ORD > Cali, Colombia: Biz from $460 Econ from $271. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cairo, Egypt: Econ from $605. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Krakow, Poland: Econ from $379. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dhaka, Bangladesh: Econ from $780. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Malaga, Spain: Econ from $411. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Boston, Massachusetts: Biz from $351 Econ from $117. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Oranjestad, Aruba: Biz from $957 Econ from $311. – Dec-Feb [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Barcelona, Spain: Econ from $372. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…