Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Salvador, El Salvador: Biz from $736 Econ from $191. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charleston, South Carolina: Econ from $104. – Dec-Feb
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Baltimore, Maryland: Econ from $78. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Punta Cana, Dominican Republic: Biz from $799 Econ from $174. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Juan, Puerto Rico: Biz from $752 Econ from $138. – 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 > Portland, Oregon: Econ from $122. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Christiansted, U.S. Virgin Islands: Biz from $1008 Econ from $199. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Marrakesh, Morocco: Econ from $481. – Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Charlotte, North Carolina: Biz from $427 Econ from $55. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1034 Econ from $223. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Biz from $532 Econ from $123. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Medellin, Colombia: Biz from $858 Econ from $250. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Salt Lake City, Utah: Econ from $116. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Boston, Massachusetts: Biz from $404 Econ from $95. – Dec-Feb
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Los Angeles, California: Econ from $113. – Dec-Feb
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
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 > San Diego, California: Econ from $118. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fort Lauderdale, Florida: Econ from $64. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Oranjestad, Aruba: Biz from $1018 Econ from $221. – Dec-Feb
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
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 > Atlanta, Georgia: Biz from $428 Econ from $35. – Dec-Feb
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
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…
MDW > New Orleans, Louisiana: Econ from $94. – Dec-Feb
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Guatemala City, Guatemala: Biz from $656 Econ from $190. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Zagreb, Croatia: Econ from $539. – Dec-Feb
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Cluj Napoca, Romania: Econ from $523. – Dec-Feb
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Nashville, Tennessee: Biz from $348 Econ from $99. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Cartagena, Colombia: Biz from $921 Econ from $223. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Montego Bay, Jamaica: Biz from $971 Econ from $254. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Vilnius, Lithuania: Biz from $1804 Econ from $444. – Dec-Feb (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…
MDW > Baltimore, Maryland: Econ from $78. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Johannesburg, South Africa: Econ from $735. – Dec-Feb
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > San Jose, Costa Rica: Biz from $1226 Econ from $233. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Entebbe, Uganda: Econ from $753. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…