Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Paris, France: Econ from $427. – Oct-Dec (Including Thanksgiving) [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 $477. – Oct-Dec (Including Thanksgiving) [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 $1,133 Econ from $365. – Nov-Jan (Including Thanksgiving) [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 > Ljubljana, Slovenia: Econ from $464. – Oct-Dec (Including Thanksgiving) [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 > London, United Kingdom: Econ from $319. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Helsinki, Finland: Econ from $416. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubai, United Arab Emirates: Econ from $518. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Krakow, Poland: Biz from $1,793 Econ from $512. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Moscow, Russia: Biz from $1,775 Econ from $329. – Oct-Dec (Including Thanksgiving) [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 > Frankfurt am Main, Germany: Econ from $292. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Nice, France: Econ from $315. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Marrakesh, Morocco: Biz from $2,110 Econ from $378. – Oct-Dec (Including Thanksgiving) [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 > Munich, Germany: Econ from $311. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Casablanca, Morocco: Econ from $372. – Oct-Dec (Including Thanksgiving) [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 $1,932 Econ from $321. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Frankfurt am Main, Germany: Econ from $290. – Oct-Dec (Including Thanksgiving) [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 $326. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dublin, Ireland: Biz from $1,133 Econ from $294. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Monterrey, Mexico: Econ from $228. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Milan, Italy: Econ from $450. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Puerto Vallarta, Mexico: Econ from $288. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Puerto Escondido, Mexico: Biz from $804 Econ from $217. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Guadalajara, Mexico: Biz from $686 Econ from $203. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dubai, United Arab Emirates: Econ from $574. – Oct-Dec (Including Thanksgiving) [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 > Philadelphia, Pennsylvania: Econ from $73. Biz from $365 (Business Bargain). – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Memphis, Tennessee: Econ from $77. Biz from $354 (Business Bargain). – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Nashville, Tennessee: Econ from $77. Biz from $354 (Business Bargain). – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Punta Gorda, Florida: Econ from $79. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Skopje, North Macedonia: From $444 round-trip – Oct-Dec (Including Thanksgiving) [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 > Minneapolis, Minnesota: From $61 round-trip – Oct-Dec (Including Thanksgiving) *BB [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Belgrade, Serbia: From $442 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Punta Gorda, Florida: From $64 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Amman, Jordan: From $432 round-trip – Oct-Dec (Including Thanksgiving) [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 > Barcelona, Spain: From $278 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Santiago, Chile: From $227 round-trip – Oct-Dec (Including Thanksgiving) *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 > Piarco, Trinidad and Tobago: From $270 round-trip – Oct-Dec (Including Thanksgiving) *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 > New Delhi, India: From $637 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cincinnati, Ohio: From $97 round-trip – Oct-Dec (Including Thanksgiving) *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Burlington, Kentucky: From $70 round-trip – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…