Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Bangkok, Thailand: Econ from $682. – Jan-Mar [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Coxen Hole, Honduras: Biz from $1424. Econ from $489. – Nov-Jan
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Thera, Greece: Econ from $674. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kinshasa, Democratic Republic of the Congo: Econ from $916. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Willemstad, Curaçao: Biz from $1080. Econ from $428. – Nov-Jan [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 $589. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Baku, Azerbaijan: Econ from $859. – Dec-Feb [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 > Dublin, Ireland: Econ from $349. – Dec-Feb [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Pedro Sula, Honduras: Biz from $503 Econ from $237. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Melbourne, Australia: Econ from $1043. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Athens, Greece: Econ from $493. – Nov-Jan [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Santo Domingo, Dominican Republic: Biz from $596 Econ from $287. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Hamburg, Germany: Econ from $515. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > George Town, Cayman Islands: Biz from $660 Econ from $305. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Belgrade, Serbia: Econ from $485. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dhaka, Bangladesh: Econ from $783. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Monterrey, Mexico: Biz from $666 Econ from $270. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Palma de Mallorca, Spain: Econ from $414. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Berlin, Germany: Econ from $434. – Jan-Mar (Presidents day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cozumel, Mexico: Biz from $1071 Econ from $323. – Jan-Mar
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Cairo, Egypt: Econ from $588. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Sapporo, Japan: Econ from $873. – Dec-Feb [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > San Juan, Puerto Rico: Econ from $138. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Porto, Portugal: Econ from $425. – Nov-Jan [SOLD OUT] [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Barranquilla, Colombia: Biz from $687. Econ from $334. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Auckland, New Zealand: Econ from $961. – Jan-Mar [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 > Malaga, Spain: Econ from $374. – Jan-Mar [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Phuket City, Thailand: Econ from $562.- Mar-May
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Larnaca, Cyprus: Econ from $496.- Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Oranjestad, Aruba: Biz from $554 Econ from $247.- Nov-Jan [SOLD OUT]
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Bucharest, Romania: Econ from $485.- Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Algiers, Algeria: Econ from $553.- Nov-Jan [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 > Toronto, Canada: Biz from $448 Econ from $135.- Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Colombo, Sri Lanka: Econ from $774. – Mar-May (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Kingston, Jamaica: Biz from $805 Econ from $367. – Jan-Mar [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Barcelona, Spain: Econ from $356. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cluj Napoca, Romania: Econ from $518. – Feb-Apr (Including Spring Break)
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Punta Cana, Dominican Republic: Biz from $722 Econ from $248. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sao Paulo, Brazil: Biz from $1877 Econ from $428. – Nov-Jan [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…