Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cancun, Mexico: Biz from $501 Econ from $187.- Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Casablanca, Morocco: Econ from $539.- 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 > Madrid, Spain: Econ from $323.- Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Managua, Nicaragua: Biz from $639 Econ from $262.- Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Almaty, Kazakhstan: Econ from $821.- Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Guadalajara, Mexico: Biz from $645 Econ from $211.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Prague, Czech Republic: Econ from $385.- Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dublin, Ireland: Econ from $345.- Jan-Mar
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 $444.- 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 > San Pedro Sula, Honduras: Biz from $489 Econ from $243.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Athens, Greece: Econ from $492. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belize City, Belize: Econ from $363. – Dec-Feb (Including Winter Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Florianopolis, Brazil: Biz from $2924 Econ from $725. – 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 > Hamburg, Germany: Econ from $467. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Tbilisi, Georgia: Econ from $561. – 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 > Santo Domingo, Dominican Republic: Biz from $521. Econ from $292. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cairns, Australia: Econ from $1088. – 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 > Kos, Greece: Econ from $667. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > George Town, Cayman Islands: Biz from $463. Econ from $271. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Monterrey, Mexico: Biz from $661 Econ from $221. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Bucharest, Romania: Econ from $489. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belgrade, Serbia: Econ from $504. – Mar-May (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Berlin, Germany: Econ from $439. – Oct-Dec (Including Thanksgiving)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Male, Maldives: Econ from $950. – Jan-Mar (Presidents day Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cali, Colombia: Biz from $460 Econ from $271. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Toronto, Canada: Biz from $550 Econ from $230. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cairo, Egypt: Econ from $605. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Krakow, Poland: Econ from $379. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dhaka, Bangladesh: Econ from $780. – Nov-Jan (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 > Barranquilla, Colombia: Biz from $499 Econ from $318. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Malaga, Spain: Econ from $411. – 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 > Oranjestad, Aruba: Biz from $957 Econ from $311. – Dec-Feb
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Barcelona, Spain: Econ from $372. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Rabat, Morocco: Econ from $529. – Nov-Jan (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 > Hong Kong, Hong Kong: Econ from $710. – Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Simpson Bay, St. Maarten: Econ from $375. – Oct-Dec (Including Thanksgiving)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Funchal, Portugal: Econ from $470. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kingston, Jamaica: Biz from $925. Econ from $352. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cluj Napoca, Romania: Econ from $486. – Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…