Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Dubai, United Arab Emirates: Econ from $553. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Phu Quoc, Vietnam: Econ from $845. – Oct-Dec [SOLD OUT]
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 $1167 Econ from $573. – 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 > Innsbruck, Austria: Econ from $595. – Jan-Mar (Presidents day Weekend)
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 $616 Econ from $311. – 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 > Gdansk, Poland: Econ from $391. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Algiers, Algeria: Econ from $580. – Nov-Jan (Including Thanksgiving) [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 > Tokyo, Japan: Econ from $741. – Apr-Jun
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Athens, Greece: Econ from $472. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cartagena, Colombia: Biz from $584 Econ from $259. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cape Town, South Africa: Econ from $1009. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > San Jose, Costa Rica: Econ from $344. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Heraklion, Greece: Econ from $549. – Oct-Dec (Including Fall Break) [SOLD OUT]
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
MDW > Krakow, Poland: Econ from $526. – 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 > Kingston, Jamaica: Biz from $780. Econ from $342. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Abu Dhabi, United Arab Emirates: Econ from $569. – Sep-Nov (Including Fall Break) [SOLD OUT]
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 $435. – 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 > Cali, Colombia: Biz from $643 Econ from $280. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Florianopolis, Brazil: Biz from $1367 Econ from $716. – Jan-Mar
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 $940. – Dec-Feb [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 $552 Econ from $241. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Mykonos, Greece: Econ from $569. – Sep-Nov (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Bucharest, Romania: Econ from $600. – Oct-Dec [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Tunis, Tunisia: Biz from $2627 Econ from $809. – Oct-Dec [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 > Managua, Nicaragua: Biz from $1012 Econ from $234. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Krabi, Thailand: Econ from $920.- Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Medellin, Colombia: Biz from $525 Econ from $228.- Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Paphos, Cyprus: Econ from $502.- Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Larnaca, Cyprus: Econ from $480.- Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Riga, Latvia: Biz from $2203 Econ from $467.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
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 $376 Econ from $201.- Oct-Dec (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Punta Cana, Dominican Republic: Econ from $357.- Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New Delhi, India: Econ from $661.- Oct-Dec [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cluj Napoca, Romania: Econ from $512.- Oct-Dec [SOLD OUT]
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Nairobi, Kenya: Econ from $813.- Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Poznan, Poland: Econ from $416.- Oct-Dec [SOLD OUT]
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 $919 Econ from $226.- Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cagliari, Italy: Econ from $699.- Sep-Nov [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 $1069 Econ from $308.- Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…