Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Poznan, Poland: Econ from $494. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Minneapolis, Minnesota: Biz from $227 Econ from $57. – Sep-Nov (Including Fall Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cincinnati, Ohio: Biz from $227 Econ from $57. – Aug-Oct
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dubrovnik, Croatia: Econ from $643. – Jan-Mar
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Monterrey, Mexico: Biz from $838 Econ from $188. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Knoxville, Tennessee: Biz from $369 Econ from $74. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Seattle, Washington: Biz from $489 Econ from $92. – Sep-Nov
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Oranjestad, Aruba: Econ from $302. – Aug-Oct
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Reykjavik, Iceland: Econ from $296. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Zagreb, Croatia: Econ from $490. – Jan-Mar
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Corfu, Greece: Econ from $642. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Los Angeles, California: Econ from $77. – Oct-Dec
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Boise, Idaho: Biz from $424 Econ from $105. – Sep-Nov (Including Fall Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Pointe La Rue, Seychelles: Econ from $816. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Piarco, Trinidad and Tobago: Biz from $934 Econ from $306. – Aug-Oct
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 $458. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Orlando, Florida: Econ from $58. – Aug-Oct
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Boston, Massachusetts: Biz from $387 Econ from $47. – Sep-Nov (Including Fall Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > San Salvador, El Salvador: Biz from $841 Econ from $236. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Split, Croatia: Econ from $488. – Sep-Nov
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Skopje, North Macedonia: Econ from $502. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cluj Napoca, Romania: Econ from $532. – Oct-Dec
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
MDW > Atlanta, Georgia: Biz from $428 Econ from $48. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Myrtle Beach, South Carolina: Econ from $45. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cancun, Mexico: Biz from $731 Econ from $199. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Madrid, Spain: Econ from $369. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Miami, Florida: Econ from $55. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Charlotte, North Carolina: Biz from $337 Econ from $51. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Kingston, Jamaica: Biz from $788 Econ from $277. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tallinn, Estonia: Econ from $378. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Athens, Greece: Econ from $481. – 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 > Abuja, Nigeria: Biz from $3388 Econ from $934. – Jan-Mar
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Newark, New Jersey: Econ from $71. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Ontario, California: Econ from $86. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guadalajara, Mexico: Biz from $815 Econ from $219. – Sep-Nov
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 $478. – Jan-Mar (Including President’s Day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Christiansted, U.S. Virgin Islands: Biz from $974 Econ from $282. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Reno, Nevada: Econ from $108. – Aug-Oct
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
ORD > New York, New York: Biz from $383 Econ from $49. – Aug-Oct
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…