Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Panama City, Panama: From $203 round-trip – Sep-Nov *BB [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Los Angeles, California: From $67 round-trip – Sep-Nov *BB [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Philadelphia, Pennsylvania: From $47 round-trip – 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 > Christiansted, U.S. Virgin Islands: From $181 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fort Lauderdale, Florida: From $33 round-trip – 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 > San Diego, California: From $37 round-trip – Sep-Nov *BB [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Oranjestad, Aruba: From $193 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
MDW > Savannah, Georgia: From $127 round-trip – Sep-Nov *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Charlotte, North Carolina: From $72 round-trip – Sep-Nov (Including Fall Break) *BB [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 > Burbank, California: From $90 round-trip – Sep-Nov *BB [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 > Kailua Kona, Hawaii: From $326 round-trip – Sep-Nov [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Jacksonville, Florida: From $119 round-trip – Sep-Nov *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Bridgetown, Barbados: From $380 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Columbia, Missouri: From $91 round-trip – Sep-Nov *BB [SOLD OUT]
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: From $74 round-trip – 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…
ORD > Miami, Florida: From $57 round-trip – 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 > Moscow, Russia: From $795 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Cleveland, Ohio: From $118 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Ithaca, New York: From $108 round-trip – Oct-Dec *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Washington, DC: From $92 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Buffalo, New York: From $91 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Memphis, Tennessee: From $108 round-trip – Sep-Nov *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cincinnati, Ohio: From $91 round-trip – Sep-Nov *BB [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 > Panama City, Panama: From $247 round-trip – Sep-Nov *BB [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Jacksonville, Florida: From $105 round-trip – Sep-Nov *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Salvador, El Salvador: From $232 round-trip – Oct-Dec *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Santiago, Chile: From $450 round-trip – Sep-Nov (Including Fall Break) *BB [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 > Missoula, Montana: From $58 round-trip – Sep-Nov *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Miami, Florida: From $56 round-trip – 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 > Piarco, Trinidad and Tobago: From $261 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Marrakesh, Morocco: From $468 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Brasilia, Brazil: From $491 round-trip – Sep-Nov *BB [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 > Chisinau, Moldova: From $443 round-trip – 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 > Charlotte, North Carolina: From $72 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Knoxville, Tennessee: From $57 round-trip – Oct-Dec *BB [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 > Omaha, Nebraska: From $91 round-trip – Sep-Nov *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Trenton, New Jersey: From $57 round-trip – 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 > George Town, Cayman Islands: From $270 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tangier, Morocco: From $436 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…