Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > New Orleans, Louisiana: From $65 round-trip – Nov-Jan [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 > Istanbul, Turkey: From $501 round-trip – Nov-Jan [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 > Lima, Peru: From $391 round-trip – Nov-Jan [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 > Amman, Jordan: From $432 round-trip – Oct-Dec (Including Thanksgiving) [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 > Columbia, Missouri: From $137 round-trip – Nov-Jan *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 > London, United Kingdom: From $394 round-trip – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Panama City, Panama: From $303 round-trip – Nov-Jan *BB [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > San Jose, Costa Rica: From $236 round-trip – Nov-Jan *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 $227 round-trip – Oct-Dec (Including Thanksgiving) *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 > Savannah, Georgia: From $75 round-trip – Nov-Jan *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 > New Delhi, India: From $637 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cincinnati, Ohio: From $97 round-trip – Oct-Dec (Including Thanksgiving) *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Mexico City, Mexico: From $208 round-trip – Nov-Jan *BB [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Decatur, Georgia: From $98 round-trip – Nov-Jan (Including Winter Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cancun, Mexico: From $160 round-trip – Nov-Jan *BB [SOLD OUT]
– Nov-Jan ORD > Cancun, Mexico: From $153 round-trip Don’t forget – most of these trips sell out within days…
ORD > Santiago, Chile: From $431 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Valparaiso, Florida: From $90 round-trip – Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cusco, Peru: From $437 round-trip – Nov-Jan *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 > London, United Kingdom: From $357 round-trip – Nov-Jan [SOLD OUT]
It’s been a while since I’ve been to London, but I’ll never forget it. We did the touristy thing and…
ORD > Barcelona, Spain: From $304 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cartagena, Colombia: From $258 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Marrakesh, Morocco: From $778 round-trip – Nov-Jan [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 > Charleston, South Carolina: From $149 round-trip – Nov-Jan *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 > Medellin, Colombia: From $313 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Zacatecas, Mexico: From $331 round-trip – Nov-Jan *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 > Porto Alegre, Brazil: From $810 round-trip – Nov-Jan (Including Winter 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 > Thera, Greece: From $486 round-trip – Nov-Jan [SOLD OUT]
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Cozumel, Mexico: From $433 round-trip – Nov-Jan *BB [SOLD OUT]
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Willemstad, Curaçao: From $484 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Anchorage, Alaska: From $342 round-trip – Dec-Feb (Including Winter 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 > Casablanca, Morocco: From $575 round-trip – Nov-Jan *BB [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 > Manchester, New Hampshire: From $149 round-trip – Nov-Jan (Including Winter 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…
ORD > Toronto, Canada: From $192 round-trip – Nov-Jan (Including Winter 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.…
MDW > San Pedro Sula, Honduras: From $620 round-trip – Nov-Jan (Including Winter 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.…
MDW > Austin, Texas: From $158 round-trip – Nov-Jan *BB [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Knoxville, Tennessee: From $65 round-trip – Nov-Jan *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cluj Napoca, Romania: From $510 round-trip – Dec-Feb (Including Winter Break) *BB [SOLD OUT]
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Fukuoka, Japan: From $567 round-trip – Nov-Jan (Including Winter Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Dublin, Ireland: From $506 round-trip – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…