For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Arequipa, Peru: Econ from $477. – Jun-Aug (Including Summer 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 > Toronto, Canada: Econ from $264. – Jul-Sep (Including Summer 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 > Kiev, Ukraine: Biz from $2,126 Econ from $582. – Apr-Jun (Including Summer 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 > Juneau, Alaska: Biz from $850 Econ from $410. – May-Jul (Including Summer 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 > Madrid, Spain: Econ from $441. – Apr-Jun (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Stockholm, Sweden: Econ from $318. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Minneapolis, Minnesota: Biz from $259 Econ from $94. – Apr-Jun (Including Summer 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 > Riga, Latvia: Biz from $1,979 Econ from $424. – Jul-Sep (Including Summer Break) [SOLDOUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Stockholm, Sweden: Econ from $274. – Apr-Jun (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Minneapolis, Minnesota: Biz from $285 Econ from $86. – Apr-Jun (Including Summer 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 > Madrid, Spain: Econ from $326. – May-Jul (Including Summer 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 > Riga, Latvia: Biz from $1,933 Econ from $527. – Jul-Sep (Including Summer Break) [SOLDOUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Budapest, Hungary: Biz from $1,379 Econ from $445. – Apr-Jun (Including Summer Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Stockholm, Sweden: Econ from $274. – May-Jul (Including Summer 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 > Paris, France: Econ from $431. – Apr-Jun (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Decatur, Georgia: Econ from $98. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Dubrovnik, Croatia: Econ from $531. – May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Santa Maria Huatulco, Mexico: Biz from $770 Econ from $214. – May-Jul (Including Summer 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 > Moscow, Russia: Econ from $466. Biz from $1,568 (Business Bargain). – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Porto, Portugal: Econ from $364. – Apr-Jun (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Split, Croatia: Econ from $467. – May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Stockholm, Sweden: Econ from $274. – Apr-Jun (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Helsinki, Finland: Econ from $399. – Apr-Jun (Including Summer Break) [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 $514. Biz from $2,101 (Business Bargain). – May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Moscow, Russia: Econ from $456. Biz from $1,568 (Business Bargain). – May-Jul (Including Summer Break) [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 > Copenhagen, Denmark: Econ from $357. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: Econ from $443. Biz from $1,438 (Business Bargain). – May-Jul (Including Summer Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Milan, Italy: Econ from $356. – May-Jul (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Stockholm, Sweden: Econ from $337. – Apr-Jun (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Split, Croatia: Econ from $519. Biz from $2,153 (Business Bargain). – May-Jul (Including Summer 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 > Dubrovnik, Croatia: Econ from $508. Biz from $1,697 (Business Bargain). – Apr-Jun (Including Summer Break) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Helsinki, Finland: Econ from $361. Biz from $__ (Business Bargain). – May-Jul (Including Summer Break) [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: From $473 round-trip – Jun-Aug (Including Fourth of July) *BB [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Marrakesh, Morocco: From $422 round-trip – May-Jul (Including Summer Break) *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 > Malaga, Spain: From $354 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Budapest, Hungary: From $397 round-trip – Jun-Aug (Including Fourth of July) *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 > Split, Croatia: From $461 round-trip – Apr-Jun (Including Summer Break) *BB [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Bilbao, Spain: From $338 round-trip – Jun-Aug (Including Summer Break) *BB [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Toronto, Canada: From $205 round-trip – May-Jul (Including Summer 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…