Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cincinnati, Ohio: Biz from $365 Econ from $108. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Knoxville, Tennessee: Econ from $82. – Sep-Nov [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Pittsburgh, Pennsylvania: Biz from $344 Econ from $103. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > New Orleans, Louisiana: Biz from $219. Econ from $97. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
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,…
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 > 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 > 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 > 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,…
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 > 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 > 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 > 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 > Charleston, South Carolina: Econ from $162. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Philadelphia, Pennsylvania: Biz from $256. Econ from $90. – 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…
MDW > Miami, Florida: Econ from $93. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Dallas, Texas: Biz from $248 Econ from $87. – 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…
ORD > Cluj Napoca, Romania: Econ from $518. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cancun, Mexico: Biz from $431 Econ from $238. – 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 > Chennai, India: Econ from $751. – 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 > Louisville, Kentucky: Biz from $307 Econ from $137. – Sep-Nov (Including Fall Break) [SOLD OUT]
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Orlando, Florida: Biz from $256 Econ from $77. – Sep-Nov (Including Fall Break) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Prague, Czech Republic: Econ from $432. – 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 > Fort Lauderdale, Florida: Biz from $343. Econ from $92. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
MDW > San Antonio, Texas: Econ from $147. – 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,…
ORD > Pittsburgh, Pennsylvania: Biz from $287. Econ from $97. – 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 > Asheville, North Carolina: Econ from $81. – Oct-Dec [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Liberia, Costa Rica: Biz from $1257 Econ from $309. – Sep-Nov (Including Fall Break) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Phu Quoc, Vietnam: Econ from $845. – 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 > New York, New York: Biz from $398 Econ from $67. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Athens, Greece: Econ from $472. – 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 > Cartagena, Colombia: Biz from $584 Econ from $259. – 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 > Austin, Texas: Biz from $523. Econ from $74. – 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 > Heraklion, Greece: Econ from $549. – Oct-Dec (Including Fall Break) [SOLD OUT]
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Los Angeles, California: Biz from $329. Econ from $87. – 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 > Atlanta, Georgia: Biz from $242. Econ from $92. – 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 > Abu Dhabi, United Arab Emirates: Econ from $569. – 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 > Birmingham, Alabama: Biz from $387 Econ from $145. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…