Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
(Including Labor Day) ORD > Cozumel, Mexico: Biz from $635 Econ from $262. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Riga, Latvia: Econ from $488. – Aug-Oct (Including Labor Day)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Split, Croatia: Econ from $543. – Aug-Oct (Including Labor Day)
* This is a “fare dump” with a few alternate dates available.
ORD > Palanga, Lithuania: Econ from $441. – Aug-Oct (Including Labor Day)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Belgrade, Serbia: Econ from $593. – Aug-Oct (Including Labor Day)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Split, Croatia: Econ from $541. – Aug-Oct (Including Labor Day)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Kansas City, Kansas: Biz from $499 Econ from $135. – Aug-Oct (Including Labor Day) [SOLD OUT]q
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Zacatecas, Mexico: Econ from $262. – Aug-Oct (Including Labor Day) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Atlantic City, New Jersey: Biz from $630 Econ from $92. – Aug-Oct (Including Labor Day) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Cancun, Mexico: Biz from $991 Econ from $206. – Aug-Oct (Including Labor Day) [SOLD OUT]
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 $71. – Aug-Oct (Including Labor Day) [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 Juan, Puerto Rico: Biz from $682 Econ from $159. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Houston, Texas: Econ from $96. – Aug-Oct (Including Labor Day) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Punta Arenas, Chile: Biz from $3042 Econ from $757. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Monterrey, Mexico: Biz from $378 Econ from $230. – Aug-Oct (Including Labor Day) [SOLD OUT] [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Morelia, Mexico: Biz from $439 Econ from $273. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Denver, Colorado: Biz from $559 Econ from $80. – Aug-Oct (Including Labor Day) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Nadi, Fiji: Econ from $846. – Aug-Oct (Including Labor Day) [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 > Christiansted, U.S. Virgin Islands: Biz from $1234 Econ from $294. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Ontario, California: Econ from $100. – Aug-Oct (Including Labor Day) [SOLDOUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > New Haven, Connecticut: Biz from $548 Econ from $114. – Aug-Oct (Including Labor Day) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Tampa, Florida: Econ from $61. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Salt Lake City, Utah: Econ from $153. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > New Orleans, Louisiana: Econ from $75. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Philadelphia, Pennsylvania: Econ from $103. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Atlantic City, New Jersey: Biz from $629 Econ from $140. – Aug-Oct (Including Labor Day) [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 Pedro Sula, Honduras: Biz from $883 Econ from $297. – Aug-Oct (Including Labor Day) [SOLDOUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Denver, Colorado: Econ from $102. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Austin, Texas: Econ from $162. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Leon, Mexico: Econ from $334. – Aug-Oct (Including Labor Day) [SOLDOUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Reykjavik, Iceland: Econ from $438. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cluj Napoca, Romania: Econ from $526. – Aug-Oct (Including Labor Day) [SOLDOUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubrovnik, Croatia: Econ from $599. – Aug-Oct (Including Labor Day) [SOLDOUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Podgorica, Montenegro: Biz from $2,712 Econ from $607. – Aug-Oct (Including Labor Day) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubrovnik, Croatia: Econ from $564. – Aug-Oct (Including Labor Day) [SOLDOUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Tallinn, Estonia: Econ from $397. – Aug-Oct (Including Labor Day) [SOLDOUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Sarajevo, Bosnia and Herzegovina: Econ from $572. – Aug-Oct (Including Labor Day) [SOLDOUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Hamburg, Germany: Econ from $475. – Aug-Oct (Including Labor Day) [SOLDOUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Malaga, Spain: Econ from $401. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…