Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Miami, Florida: Biz from $206. Econ from $68. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Houston, Texas: Econ from $78. – Oct-Dec
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Cluj Napoca, Romania: Econ from $486. – 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…
ORD > Algiers, Algeria: Econ from $539. – Nov-Jan (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
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 > Dallas, Texas: Econ from $64. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Auckland, New Zealand: Econ from $1019. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Poznan, Poland: Econ from $448. – Oct-Dec (Including Thanksgiving)
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 $438 Econ from $202. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Colombo, Sri Lanka: Econ from $733. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Portland, Oregon: Econ from $158. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Prague, Czech Republic: Econ from $401. – Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Louisville, Kentucky: Biz from $320 Econ from $94. – Oct-Dec (Including Thanksgiving)
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Madrid, Spain: Econ from $326. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Orlando, Florida: Biz from $251 Econ from $80. – Nov-Jan
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Casablanca, Morocco: Econ from $528. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Guadalajara, Mexico: Biz from $771 Econ from $202. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Antonio, Texas: Econ from $154. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
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…
MDW > Dubai, United Arab Emirates: Econ from $741. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Palma de Mallorca, Spain: Econ from $402. – 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 > Managua, Nicaragua: Biz from $774 Econ from $234. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Diego, California: Econ from $153. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
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…
ORD > Dublin, Ireland: Econ from $374. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Liberia, Costa Rica: Biz from $952. Econ from $307. – Dec-Feb
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Belize City, Belize: Biz from $696. Econ from $376. – Nov-Jan
* This is a “fare dump” with a few alternate dates available.
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…
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…
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 > 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 > 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,…
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…