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 $1140 Econ from $186. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Baltimore, Maryland: Econ from $78. – 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 > 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…
ORD > Sharjah, United Arab Emirates: Econ from $787. – Dec-Feb
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Ontario, California: Econ from $88. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Reno, Nevada: Econ from $130. – Dec-Feb
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Durban, South Africa: Econ from $1068. – Dec-Feb
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Atlantic City, New Jersey: Biz from $654 Econ from $94. – 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 $1036 Econ from $175. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Burbank, California: Econ from $152. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Juan, Puerto Rico: Biz from $797 Econ from $111. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Algiers, Algeria: Econ from $748. – Dec-Feb
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Myrtle Beach, South Carolina: Econ from $122. – 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 > Denver, Colorado: Biz from $498 Econ from $38. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Philadelphia, Pennsylvania: Econ from $38. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Dallas, Texas: Biz from $567 Econ from $38. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Christiansted, U.S. Virgin Islands: Biz from $1058 Econ from $184. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Honolulu, Hawaii: Econ from $321. – Dec-Feb
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Santo Domingo, Dominican Republic: Biz from $820 Econ from $226. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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…
PHX > Madison, Wisconsin: Econ from $136. – 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 > Los Angeles, California: Econ from $118. – Jan-Mar
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 > Hartford, Connecticut: Biz from $607 Econ from $98. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Guayaquil, Ecuador: Biz from $1028 Econ from $308. – Dec-Feb
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
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…
ORD > Panama City, Panama: Biz from $1058 Econ from $396. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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 > Nashville, Tennessee: Biz from $420 Econ from $92. – Dec-Feb
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
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 > Houston, Texas: Econ from $98. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Santa Ana, California: Econ from $104. – Dec-Feb
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.…