Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cincinnati, Ohio: Biz from $277 Econ from $133. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Pittsburgh, Pennsylvania: Biz from $327 Econ from $99. – Sep-Nov [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Buffalo, New York: Biz from $339 Econ from $133. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Nairobi, Kenya: Econ from $620. – 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…
MDW > Saint Thomas Island, U.S. Virgin Islands: Biz from $1,066 Econ from $428. – 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.…
MDW > Anchorage, Alaska: Econ from $325. – 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 > Nashville, Tennessee: Biz from $287 Econ from $99. – Sep-Nov (Including Fall Break) [SOLD OUT]
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > Leon, Mexico: Biz from $491 Econ from $280. – 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.…
MDW > Lima, Peru: Biz from $995 Econ from $445. – 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 > Managua, Nicaragua: Biz from $616 Econ from $343. – 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 > Porto, Portugal: Econ from $280. – 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 > Lisbon, Portugal: Econ from $296. – 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 > Cincinnati, Ohio: Biz from $251 Econ from $133. – 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 > Mexico City, Mexico: Biz from $510 Econ from $184. – Oct-Dec [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > London, United Kingdom: Econ from $362. – 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 > Brussels, Belgium: Econ from $309. – 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 > Memphis, Tennessee: Biz from $277 Econ from $99. – 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 > Austin, Texas: Econ from $56. – Sep-Nov [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Tokyo, Japan: Econ from $883. – 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 > Lima, Peru: Biz from $935 Econ from $405. – 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…
MDW > Guadalajara, Mexico: Biz from $669 Econ from $224. – 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 > Saint Petersburg, Russia: Biz from $2,056 Econ from $463. – 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 > Lisbon, Portugal: Econ from $340. – Sep-Nov [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Quito, Ecuador: Biz from $1,061 Econ from $335. – 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 > Arequipa, Peru: Biz from $1,420 Econ from $475. – 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 > Fairbanks, Alaska: Biz from $787 Econ from $308. – Sep-Nov [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Paris, France: Econ from $385. – 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 > Moscow, Russia: Biz from $1,607 Econ from $542. – 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 > Fairbanks, Alaska: Biz from $828 Econ from $308. – 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 > Santiago de Compostela, Spain: Biz from $900 Econ from $390. – 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 > Stockholm, Sweden: Econ from $356. – 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 > Budapest, Hungary: Biz from $1,417 Econ from $483. – Oct-Dec [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 > Casablanca, Morocco: Biz from $1,822 Econ from $291. – 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 > Dublin, Ireland: Biz from $1,270 Econ from $370. – 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 > Accra, Ghana: Biz from $1,911 Econ from $387. – 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 > Nice, France: Econ from $313. – Sep-Nov (Including Fall Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Halifax, Canada: Econ from $220. – 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 > Milan, Italy: Econ from $381. – 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 > Las Palmas de Gran Canaria, Spain: Econ from $372. – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…