For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Heraklion, Greece: Econ from $702. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Krakow, Poland: Econ from $533. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Johannesburg, South Africa: Econ from $757. – Oct-Dec
* This is a “fare dump” with a few alternate dates available.
MDW > Warsaw, Poland: Econ from $511. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Dubai, United Arab Emirates: Econ from $1046. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Dubai, United Arab Emirates: Econ from $675. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cape Town, South Africa: Econ from $940. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Luqa, Malta: Econ from $591. – Nov-Jan (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Madrid, Spain: Econ from $495. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Johannesburg, South Africa: Econ from $757. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Dubai, United Arab Emirates: Econ from $674. – Oct-Dec (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Male, Maldives: Econ from $903. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Johannesburg, South Africa: Econ from $757. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Marrakesh, Morocco: Econ from $598. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dubai, United Arab Emirates: Econ from $695. – Nov-Jan
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: Econ from $483. – Oct-Dec
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 $397. – Nov-Jan (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Iasi, Romania: Econ from $621. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > San Diego, California: Econ from $88. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Philadelphia, Pennsylvania: Econ from $38. – Oct-Dec (Including Thanksgiving)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Ontario, California: Econ from $88. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Baltimore, Maryland: Econ from $88. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Los Angeles, California: Biz from $508 Econ from $106. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Christiansted, U.S. Virgin Islands: Biz from $983 Econ from $235. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Hartford, Connecticut: Biz from $597 Econ from $108. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Casablanca, Morocco: Econ from $485. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Las Vegas, Nevada: Econ from $73. – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Algiers, Algeria: Econ from $463. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Male, Maldives: Econ from $843. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Larnaca, Cyprus: Econ from $461. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Belgrade, Serbia: Econ from $608. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Sacramento, California: Econ from $111. – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $220. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Curitiba, Brazil: Econ from $809. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Raleigh, North Carolina: Biz from $408 Econ from $50. – Oct-Dec
3 different flights to/from Raleigh – All under $100 round-trip. * This is an airline sale that is time-sensitive. Plenty…
ORD > Abu Dhabi, United Arab Emirates: Econ from $641. – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Houston, Texas: Econ from $104. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Marrakesh, Morocco: Econ from $577. – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Skopje, North Macedonia: Econ from $535. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…