Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Lviv, Ukraine: Biz from $2,092 Econ from $652. – May-Jul (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 > Moscow, Russia: Econ from $414. – May-Jul (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 > Budapest, Hungary: Econ from $475. – 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 > Stockholm, Sweden: Econ from $315. – Jul-Sep (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 > Ketchikan, Alaska: Biz from $734 Econ from $254. – 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 > Mexico City, Mexico: Biz from $489 Econ from $167. – Apr-Jun (Including Summer Break) [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 > Copenhagen, Denmark: Econ from $311. – Jun-Aug (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 > Marrakesh, Morocco: Econ from $528. – May-Jul (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 > Nashville, Tennessee: Biz from $275 Econ from $97. – May-Jul (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 > Arequipa, Peru: Biz from $1,571 Econ from $481. – Jun-Aug (Including Fourth of July) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Quito, Ecuador: Biz from $1,107 Econ from $335. – 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 > Fairbanks, Alaska: Biz from $857 Econ from $232. – 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…
MDW > Lisbon, Portugal: Econ from $359. – 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 > Amman, Jordan: Econ from $626. – 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 > Minneapolis, Minnesota: Biz from $235 Econ from $85. – May-Jul (Including Summer Break) [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is an airline…
ORD > Santiago, Chile: Biz from $1,390 Econ from $516. – 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 > Clarksburg, West Virginia: Econ from $54. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Clarksburg, West Virginia: Econ from $54. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Juneau, Alaska: Biz from $922 Econ from $362. – Jun-Aug (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 > Casablanca, Morocco: Biz from $2,229 Econ from $557. – 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 > Ketchikan, Alaska: Biz from $837 Econ from $358. – May-Jul (Including Summer Break) [SOLD OUT] [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Anchorage, Alaska: Biz from $810 Econ from $279. – 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…
MDW > Lima, Peru: Biz from $1,114 Econ from $405. – 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…
MDW > Clarksburg, West Virginia: Econ from $62. – Jun-Aug (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Riga, Latvia: Biz from $1,911 Econ from $569. – 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 > Faro, Portugal: Biz from $1,341 Econ from $377. – Jun-Aug (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 > Lisbon, Portugal: Econ from $342. – 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…
MDW > Anchorage, Alaska: Econ from $337. – 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 > Reykjavik, Iceland: Econ from $396. – Jun-Aug (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 > Berlin, Germany: Biz from $1,203 Econ from $454. – 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 > Accra, Ghana: Biz from $1,911 Econ from $384. – 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 > Sitka, Alaska: Biz from $929 Econ from $379. – 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 > Reykjavik, Iceland: Econ from $379. – Jun-Aug (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 > Sacramento, California: Biz from $543 Econ from $78. – Feb-Apr (Including Spring Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Ketchikan, Alaska: Biz from $846 Econ from $410. – Jun-Aug (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 > Arequipa, Peru: Econ from $482. – Jun-Aug (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 > Casablanca, Morocco: Econ from $396. – 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 > Marrakesh, Morocco: Biz from $2,087 Econ from $461. – 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 > Moscow, Russia: Biz from $1,608 Econ from $515. – 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…