Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Tallinn, Estonia: Econ from $427. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Thera, Greece: Econ from $754. – Sep-Nov [SOLD OUT]
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
MDW > Miami, Florida: Econ from $76. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Poznan, Poland: Econ from $421. – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Durban, South Africa: Econ from $932. – Sep-Nov (Including Fall Break) [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 > Vienna, Austria: Econ from $704. – Oct-Dec (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Pedro Sula, Honduras: Biz from $1007 Econ from $410. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tunis, Tunisia: Biz from $2817 Econ from $859. – Oct-Dec [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 > Riga, Latvia: Econ from $521. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Vilnius, Lithuania: Econ from $400. – Sep-Nov (Including Fall Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Santiago, Chile: Econ from $610. – Sep-Nov (Including Fall Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Warsaw, Poland: Econ from $551. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Krakow, Poland: Econ from $492. – Sep-Nov (Including Fall Break) [SOLD OUT]
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
MDW > Phoenix, Arizona: Econ from $120. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Tirana, Albania: Econ from $509. – Oct-Dec (Including Fall Break) [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 > Prague, Czech Republic: Econ from $555. – Oct-Dec (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > St. John’s, Antigua And Barbuda: Econ from $353. – Sep-Nov (Including Fall Break) [SOLD OUT]
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…
ORD > Vijayawada, India: Econ from $726. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Guatemala City, Guatemala: Econ from $246. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Heraklion, Greece: Econ from $770. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Ahmedabad, India: Econ from $636. – Sep-Nov [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 > Gdansk, Poland: Econ from $518. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Francisco, California: Econ from $168. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Abidjan, Ivory Coast: Econ from $845. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > George Town, Cayman Islands: Econ from $403. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dublin, Ireland: Econ from $413. – Sep-Nov (Including Fall Break) [SOLD OUT]
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 $516. – Sep-Nov (Including Fall Break) [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 > Vienna, Austria: Econ from $598. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Oslo, Norway: Econ from $423. – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > New York, New York: Biz from $438 Econ from $106. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Krakow, Poland: Econ from $492. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Warsaw, Poland: Econ from $552. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Econ from $639. – Sep-Nov (Including Fall 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 > Kinshasa, Democratic Republic of the Congo: Econ from $885. – Sep-Nov [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kochi, India: Econ from $634. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Abuja, Nigeria: Econ from $927. – Sep-Nov [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 > Sofia, Bulgaria: Econ from $584. – Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Bridgetown, Barbados: Econ from $385. – 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 > Budapest, Hungary: Econ from $525. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…