Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Larnaca, Cyprus: Econ from $634. – 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…
ORD > Johannesburg, South Africa: Econ from $787. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Jacksonville, Florida: Econ from $108. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Denver, Colorado: Biz from $417 Econ from $56. – Sep-Nov (Including Fall Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Jose, Costa Rica: Biz from $1171 Econ from $213. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Burbank, California: Econ from $91. – Sep-Nov
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Houston, Texas: Biz from $527 Econ from $54. – Sep-Nov
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Porto, Portugal: Econ from $455. – Nov-Jan (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Montego Bay, Jamaica: Biz from $1101 Econ from $322. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Budapest, Hungary: Econ from $502. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Barcelona, Spain: Econ from $341. – 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 > Dubai, United Arab Emirates: Econ from $591. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Albuquerque, New Mexico: Econ from $116. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Santa Ana, California: Econ from $98. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Managua, Nicaragua: Biz from $929 Econ from $328. – Sep-Nov
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sofia, Bulgaria: Econ from $502. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Dallas, Texas: Biz from $563 Econ from $58. – Aug-Oct
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Myrtle Beach, South Carolina: Econ from $48. – 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 > Sarajevo, Bosnia and Herzegovina: Econ from $499. – Nov-Jan (Including Winter Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Pedro Sula, Honduras: Biz from $1076 Econ from $291. – 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 > Krakow, Poland: Econ from $532. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > New Orleans, Louisiana: Biz from $414 Econ from $72. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fort Lauderdale, Florida: Econ from $66. – Sep-Nov
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cape Town, South Africa: Econ from $919. – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > San Juan, Puerto Rico: Econ from $124. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Las Vegas, Nevada: Econ from $50. – Sep-Nov
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > San Diego, California: Econ from $63. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Willemstad, Curaçao: Biz from $1172 Econ from $444. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Mykonos, Greece: Econ from $647. – 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…
ORD > Guayaquil, Ecuador: Biz from $922 Econ from $285. – Sep-Nov
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cozumel, Mexico: Biz from $896 Econ from $199. – Sep-Nov
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Thera, Greece: Econ from $633. – 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…
ORD > Portland, Oregon: Econ from $76. – Sep-Nov
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Phoenix, Arizona: Econ from $63. – Aug-Oct
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Tunis, Tunisia: Biz from $2726 Econ from $781. – Sep-Nov (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…
MDW > Belgrade, Serbia: Econ from $552. – Dec-Feb (Including Winter Break)
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 $634. – 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 > Asheville, North Carolina: Econ from $79. – 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 > Nashville, Tennessee: Biz from $247 Econ from $57. – Sep-Nov (Including Fall Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…