Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Heraklion, Greece: Econ from $621. – 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 > Cincinnati, Ohio: Biz from $348 Econ from $108. – 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 > Belgrade, Serbia: Econ from $479. – 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 > Salzburg, Austria: Econ from $504. – Dec-Feb (Including MLK Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Orlando, Florida: Econ from $96. – Oct-Dec
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 $332 Econ from $58. – Sep-Nov
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > San Salvador, El Salvador: Biz from $770 Econ from $228. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Vilnius, Lithuania: Econ from $434. – Oct-Dec (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Iasi, Romania: Econ from $534. – 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…
ORD > Monterrey, Mexico: Econ from $222. – 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 > Oakland, California: Econ from $105. – Sep-Nov
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 $499 Econ from $66. – Sep-Nov
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Rio de Janeiro, Brazil: Biz from $2738 Econ from $485. – 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…
MDW > Los Angeles, California: Econ from $100. – Sep-Nov (Including Fall Break)
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Charlotte, North Carolina: Biz from $358 Econ from $55. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Gdansk, Poland: Econ from $485. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Casablanca, Morocco: Econ from $496. – Oct-Dec (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 > Madrid, Spain: Econ from $355. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Marrakesh, Morocco: Econ from $490. – Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Newark, New Jersey: Biz from $433 Econ from $73. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Ontario, California: Econ from $106. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Christiansted, U.S. Virgin Islands: Biz from $918 Econ from $258. – Sep-Nov (Including Fall Break)
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 $381. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Boston, Massachusetts: Biz from $412 Econ from $46. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Split, Croatia: Econ from $484. – Sep-Nov (Including Fall Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Cancun, Mexico: Biz from $699 Econ from $176. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Bucharest, Romania: Econ from $536. – 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 $939 Econ from $337. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Hartford, Connecticut: Biz from $593 Econ from $108. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Atlanta, Georgia: Biz from $437 Econ from $56. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Pristina, Kosovo: Econ from $488. – Oct-Dec (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 > Dublin, Ireland: Econ from $381. – Nov-Jan (Including Winter Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Raleigh, North Carolina: Biz from $446 Econ from $58. – Oct-Dec
3 different flights to/from Raleigh – All under $100 round-trip. * This is an airline sale that is time-sensitive. Plenty…
MDW > Philadelphia, Pennsylvania: Econ from $55. – Aug-Oct
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Guatemala City, Guatemala: Biz from $884 Econ from $206. – Sep-Nov
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 $482. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Podgorica, Montenegro: Biz from $2661 Econ from $581. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Sacramento, California: Econ from $77. – Sep-Nov
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Tirana, Albania: Biz from $2656 Econ from $498. – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…