Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cairo, Egypt: Econ from $762. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Thera, Greece: Econ from $650. – Sep-Nov
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Luqa, Malta: Econ from $638. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Rzeszow, Poland: Econ from $632. – Oct-Dec
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Ljubljana, Slovenia: Econ from $669. – Aug-Oct
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Heraklion, Greece: Econ from $680. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Athens, Greece: Econ from $655. – Aug-Oct (Including Labor Day)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dubrovnik, Croatia: Econ from $626. – Mar-May
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Portland, Maine: Econ from $98. – Jun-Aug (Including Fourth of July and Summer Break)
I rarely post trips to Portland because they are typically so expensive. Snatch this one up before someone else does.…
ORD > Budapest, Hungary: Econ from $560. – Oct-Dec (Including Fall Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cluj Napoca, Romania: Econ from $571. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Prague, Czech Republic: Econ from $588. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Ahmedabad, India: Econ from $592. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Pula, Croatia: Biz from $2298 Econ from $589. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Zagreb, Croatia: Econ from $522. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Belgrade, Serbia: Biz from $2210 Econ from $607. – Sep-Nov (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cairo, Egypt: Econ from $803. – Nov-Jan (Including Winter Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Thera, Greece: Econ from $674. – Sep-Nov
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Barcelona, Spain: Econ from $517. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Heraklion, Greece: Econ from $658. – Sep-Nov (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
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…
MDW > Gdansk, Poland: Econ from $538. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kos, Greece: Econ from $670. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Malaga, Spain: Econ from $528. – Dec-Feb (Including MLK Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kochi, India: Econ from $752. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1153. Econ from $566. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Ahmedabad, India: Econ from $758. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
(Including Fall Break) ORD > Cluj Napoca, Romania: Econ from $579. – Sep-Nov
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dublin, Ireland: Econ from $425. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Larnaca, Cyprus: Econ from $629. – Aug-Oct
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 $692. – Sep-Nov (Including Fall Break)
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 $528. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Buenos Aires, Argentina: Biz from $2596 Econ from $742. – Apr-Jun
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Madrid, Spain: Econ from $497. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Belgrade, Serbia: Biz from $2332 Econ from $595. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cairo, Egypt: Econ from $784. – Sep-Nov
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Bucharest, Romania: Econ from $535. – Sep-Nov
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget budgetbudget two or three times…
ORD > Casablanca, Morocco: Econ from $671. – Sep-Nov (Including Fall Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Thera, Greece: Econ from $650. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…