* This is a “fare dump” with a few alternate dates available.
ORD > Georgetown, Guyana: Biz from $1258. Econ from $439. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Asheville, North Carolina: Econ from $80. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Newark, New Jersey: Econ from $58. – Oct-Dec
Have you ever booked a cruise only to find out that the flight to get there was going to be…
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…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1168 Econ from $573. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > New York, New York: Biz from $191 Econ from $78. – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Denver, Colorado: Biz from $423 Econ from $74. – Oct-Dec
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Florianopolis, Brazil: Biz from $2102 Econ from $808. – Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Innsbruck, Austria: Econ from $545. – 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…
MDW > Tampa, Florida: Biz from $368 Econ from $119. – 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 > Ontario, California: Econ from $146. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Tokyo, Japan: Econ from $680. – 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 > Athens, Greece: Econ from $456. – 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 > George Town, Cayman Islands: Biz from $619 Econ from $320. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cape Town, South Africa: Econ from $1000. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Heraklion, Greece: Econ from $642. – Oct-Dec
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Phoenix, Arizona: Econ from $99. – Oct-Dec [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Nashville, Tennessee: Biz from $206 Econ from $68. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > San Jose, Costa Rica: Biz from $702 Econ from $326. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Berlin, Germany: Econ from $438. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Los Angeles, California: Biz from $539 Econ from $131. – 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: Biz from $346 Econ from $117. – Nov-Jan
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Male, Maldives: Econ from $942. – Oct-Dec [SOLD OUT]
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 $833 Econ from $287. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Baltimore, Maryland: Econ from $96.- Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Atlanta, Georgia: Biz from $497 Econ from $65.- Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Krakow, Poland: Econ from $490.- Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Montego Bay, Jamaica: Biz from $535 Econ from $266.- 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 > Riga, Latvia: Econ from $439.- Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Washington, DC: Econ from $104. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Toronto, Canada: Biz from $534. Econ from $227. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $287. Econ from $88. – Oct-Dec (Including Thanksgiving)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Abu Dhabi, United Arab Emirates: Econ from $796. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Malaga, Spain: Econ from $436. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Rome, Italy: Econ from $338. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Raleigh, North Carolina: Biz from $320. Econ from $102. – Sep-Nov (Including Fall Break) [SOLD OUT]
My brother sent my Nephew to visit us for a weekend thanks to cheap fares to Raleigh. Watch this video…
ORD > Boston, Massachusetts: Biz from $369. Econ from $117. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Cairo, Egypt: Econ from $671. – 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 > Barranquilla, Colombia: Biz from $497. Econ from $273. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…