Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Boston, Massachusetts: Econ from $80. – Mar-May
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
MDW > Quito, Ecuador: Econ from $375. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Washington, DC: Econ from $38. – Mar-May
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 $893 Econ from $222. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Seattle, Washington: Biz from $629 Econ from $119. – Mar-May
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Norfolk, Virginia: Econ from $85. – Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Belgrade, Serbia: Econ from $584. – Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cincinnati, Ohio: Biz from $267 Econ from $97. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cagliari, Italy: Econ from $764. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Raleigh, North Carolina: Biz from $389 Econ from $48. – Mar-May
3 different flights to/from Raleigh – All under $100 round-trip. * This is an airline sale that is time-sensitive. Plenty…
ORD > Cairo, Egypt: Econ from $609. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Francisco, California: Econ from $98. – Mar-May
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
MDW > Bucharest, Romania: Econ from $571. – Mar-May (Including Spring Break)
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget budgetbudget two or three times…
MDW > Houston, Texas: Econ from $53. – Mar-May
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Riga, Latvia: Econ from $471. – 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 > Managua, Nicaragua: Biz from $816 Econ from $194. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Thera, Greece: Econ from $686. – Mar-May
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Myrtle Beach, South Carolina: Econ from $112. – Mar-May
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 $120. – Mar-May
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 $1129 Econ from $238. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Poznan, Poland: Econ from $510. – Mar-May
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
MDW > Baltimore, Maryland: Econ from $58. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Miami, Florida: Econ from $37. – Mar-May
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Jose, Costa Rica: Biz from $1271 Econ from $225. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Madrid, Spain: Econ from $375. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cape Town, South Africa: Econ from $890. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Phoenix, Arizona: Econ from $74. – Mar-May
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > San Salvador, El Salvador: Biz from $724 Econ from $199. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New Orleans, Louisiana: Biz from $409 Econ from $64. – Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Atlanta, Georgia: Biz from $389 Econ from $38. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Entebbe, Uganda: Econ from $746. – 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 > Bogota, Colombia: Biz from $829 Econ from $141. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Athens, Greece: Econ from $492. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Kansas City, Kansas: Biz from $297 Econ from $107. – Mar-May
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > New York, New York: Econ from $82. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Pedro Sula, Honduras: Biz from $674 Econ from $229. – Mar-May
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 $656. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Minneapolis, Minnesota: Biz from $287 Econ from $77. – Mar-May
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * There only appear to…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1760 Econ from $538. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…