Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Malaga, Spain: From $332 round-trip – Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Huntsville, Alabama: From $118 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 > Kansas City, Kansas: 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…
ORD > Dallas, Texas: From $45 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Anchorage, Alaska: From $214 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 > Bucharest, Romania: From $476 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget budgetbudget two or three times…
ORD > Warsaw, Poland: From $502 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Grenada, Grenada: From $266 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 > Belgrade, Serbia: From $525 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 > Cluj Napoca, Romania: From $476 round-trip – Sep-Nov [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Guadalajara, Mexico: From $187 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Krakow, Poland: From $807 round-trip – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Gaborone, Botswana: From $687 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…
ORD > Algiers, Algeria: From $529 round-trip – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cluj Napoca, Romania: From $494 round-trip – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Bucharest, Romania: From $476 round-trip – Sep-Nov [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Thera, Greece: From $715 round-trip – Sep-Nov [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Paris, France: From $378 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Morelia, Mexico: From $213 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Leon, Mexico: From $170 round-trip – Oct-Dec [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Kailua Kona, Hawaii: From $376 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Dallas, Texas: From $75 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family in Dallas? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Mykonos, Greece: From $633 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Krakow, Poland: From $514 round-trip – Oct-Dec [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Bucharest, Romania: From $489 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Guadalajara, Mexico: From $172 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 > Thera, Greece: From $668 round-trip – Oct-Dec [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
MDW > Knoxville, Tennessee: From $77 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family in Knoxville? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Zagreb, Croatia: From $606 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Tampa, Florida: From $95 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family in Tampa? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Baltimore, Maryland: From $75 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
Have friends or family in Baltimore? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > San Jose, Costa Rica: From $325 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Zagreb, Croatia: From $631 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Dublin, Ireland: From $481 round-trip – Oct-Dec [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > London, United Kingdom: From $377 round-trip – Sep-Nov [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 > Prague, Czech Republic: From $409 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Lisbon, Portugal: From $435 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Cape Town, South Africa: From $776 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Dublin, Ireland: From $473 round-trip – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.