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…
ORD > Fort Dodge, Iowa: Econ from $150. – Aug-Oct (Including Labor Day) [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 > Cairo, Egypt: Biz from $2,141 Econ from $579. – Aug-Oct (Including Labor Day) [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 > Riga, Latvia: Econ from $405. – 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 > Split, Croatia: Econ from $431. – Aug-Oct (Including Labor Day) [SOLDOUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Leon, Mexico: Biz from $676 Econ from $153. – 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 > Bogota, Colombia: Biz from $749 Econ from $214. – 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 > Juneau, Alaska: Econ from $337. – 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 > Miami, Florida: Econ from $63. – Aug-Oct (Including Labor Day) [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 > San Jose, Costa Rica: Biz from $1,075 Econ from $200. – 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 > Pittsburgh, Pennsylvania: Biz from $379 Econ from $101. – 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 > Monterrey, Mexico: Econ from $284. – 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 > Bogota, Colombia: Biz from $759 Econ from $210. – 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 > Barranquilla, Colombia: Biz from $843 Econ from $197. – 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 > Iquitos, Peru: Econ from $389. – 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 > Arequipa, Peru: Biz from $1,136 Econ from $483. – 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 > Dallas, Texas: Biz from $408 Econ from $84. – 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 > Cancun, Mexico: Biz from $701 Econ from $219. – 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 > San Salvador, El Salvador: Biz from $675 Econ from $237. – 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 > Guayaquil, Ecuador: Biz from $870 Econ from $347. – 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 > Nashville, Tennessee: Biz from $327 Econ from $97. – Aug-Oct (Including Labor Day) [SOLDOUT]
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > Guayaquil, Ecuador: Biz from $808 Econ from $404. – 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 > Pensacola, Florida: Econ from $69. – Aug-Oct (Including Labor Day) [SOLDOUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Juneau, Alaska: Biz from $967 Econ from $317. – Aug-Oct (Including Labor Day) [SOLDOUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Bogota, Colombia: Biz from $742 Econ from $273. – 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 > Pittsburgh, Pennsylvania: Biz from $353 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 > Cancun, Mexico: Biz from $655 Econ from $213. – 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 > Riga, Latvia: Biz from $1,726 Econ from $555. – 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 > San Juan, Puerto Rico: Biz from $703 Econ from $187. – 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 > Wichita, Kansas: Biz from $375 Econ from $107. – 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 > Guadalajara, Mexico: Biz from $646 Econ from $209. – 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 > Phoenix, Arizona: Econ from $119. – 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…
ORD > Rio de Janeiro, Brazil: Biz from $1,558 Econ from $599. – Aug-Oct (Including Labor Day) [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 > Juneau, Alaska: Biz from $888 Econ from $268. – 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 > Reykjavik, Iceland: Econ from $413. – 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 > Riga, Latvia: Biz from $1,744 Econ from $441. – 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 > Cleveland, Ohio: Biz from $331 Econ from $133. – 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…