Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Casablanca, Morocco: Econ from $506. – Aug-Oct
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Abuja, Nigeria: Econ from $972. – Sep-Nov
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Dubrovnik, Croatia: Econ from $616. – Sep-Nov
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Warsaw, Poland: Econ from $516. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Algiers, Algeria: Econ from $692. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
(Including Labor Day) ORD > Cozumel, Mexico: Biz from $635 Econ from $262. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
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 > Luqa, Malta: Econ from $645. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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 > 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…
ORD > Georgetown, Guyana: Biz from $1,060 Econ from $441. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Prague, Czech Republic: Econ from $541. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Riga, Latvia: Econ from $488. – Aug-Oct (Including Labor Day)
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 $507. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Econ from $589. – Aug-Oct
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Krakow, Poland: Econ from $569. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubrovnik, Croatia: Econ from $599. – Aug-Oct
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Mykonos, Greece: Econ from $760. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Guadalajara, Mexico: Biz from $829 Econ from $169. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dubrovnik, Croatia: Biz from $2622 Econ from $600. – Sep-Nov
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Mykonos, Greece: Econ from $718. – Aug-Oct
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Tivat, Montenegro: Biz from $2623 Econ from $701. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Split, Croatia: Econ from $543. – Aug-Oct (Including Labor Day)
* This is a “fare dump” with a few alternate dates available.
ORD > Palanga, Lithuania: Econ from $441. – Aug-Oct (Including Labor Day)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Barcelona, Spain: Econ from $434. – Aug-Oct
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Belgrade, Serbia: Econ from $593. – Aug-Oct (Including Labor Day)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Palma de Mallorca, Spain: Econ from $536. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Split, Croatia: Econ from $541. – Aug-Oct (Including Labor Day)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Nadi, Fiji: Econ from $1028. – Aug-Oct (Including Labor Day)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Prague, Czech Republic: Econ from $440. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Palma de Mallorca, Spain: Econ from $405. – Aug-Oct
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 $304. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Gdansk, Poland: Econ from $432. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Prague, Czech Republic: Econ from $493. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Anchorage, Alaska: Econ from $304. – Aug-Oct
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 $408. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Split, Croatia: Econ from $487. – Aug-Oct
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Split, Croatia: Econ from $409. – Aug-Oct
* This is a “fare dump” with a few alternate dates available.