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. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Phoenix, Arizona: Econ from $56. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Salt Lake City, Utah: Econ from $88. – 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 > Charlotte, North Carolina: Biz from $407 Econ from $58. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cairo, Egypt: Econ from $699. – Dec-Feb (Including MLK Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Tirana, Albania: Econ from $569. – Dec-Feb (Including MLK Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Boston, Massachusetts: Biz from $428 Econ from $98. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Podgorica, Montenegro: Biz from $2594 Econ from $621. – 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…
MDW > Boise, Idaho: Biz from $716 Econ from $126. – Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Diego, California: Econ from $110. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Sacramento, California: Econ from $141. – Dec-Feb (Including MLK Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > San Francisco, California: Biz from $608 Econ from $110. – Dec-Feb (Including MLK Weekend)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Cancun, Mexico: Biz from $667 Econ from $154. – 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…
ORD > Managua, Nicaragua: Biz from $1162 Econ from $200. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Casablanca, Morocco: Econ from $481. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Wroclaw, Poland: Econ from $510. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Quito, Ecuador: Biz from $930 Econ from $298. – Dec-Feb (Including MLK Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Kingston, Jamaica: Biz from $706 Econ from $295. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Podgorica, Montenegro: Biz from $2621 Econ from $622. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Tirana, Albania: Biz from $2643 Econ from $514. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Algiers, Algeria: Econ from $516. – Dec-Feb (Including MLK Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Vienna, Austria: Econ from $536. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > New York, New York: Biz from $388 Econ from $76. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guadalajara, Mexico: Biz from $788 Econ from $218. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Pedro Sula, Honduras: Biz from $920 Econ from $265. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $407 Econ from $56. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Guatemala City, Guatemala: Econ from $180. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kinshasa, Democratic Republic of the Congo: Econ from $888. – 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 > Maputo, Mozambique: Econ from $1125. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Salvador, El Salvador: Biz from $918 Econ from $223. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Casablanca, Morocco: Econ from $630. – Dec-Feb (Including MLK Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cozumel, Mexico: Biz from $846 Econ from $275. – Dec-Feb (Including MLK Weekend)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Kralendijk, Caribbean Netherlands: Econ from $564. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kinshasa, Democratic Republic of the Congo: Econ from $882. – 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 > Sofia, Bulgaria: Econ from $581. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1623 Econ from $484. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dubrovnik, Croatia: Econ from $630. – Dec-Feb (Including MLK Weekend)
* This is a “fare dump” with a few alternate dates available.
ORD > Casablanca, Morocco: Econ from $541. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Porto, Portugal: Econ from $512. – Dec-Feb (Including MLK Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…