Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Panama City, Panama: Biz from $914 Econ from $446. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Bogota, Colombia: Biz from $783 Econ from $314. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Los Angeles, California: Econ from $94. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Dallas, Texas: Econ from $63. – Apr-Jun (Including Summer Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cartagena, Colombia: Biz from $977 Econ from $266. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Atlantic City, New Jersey: Econ from $124. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > New Orleans, Louisiana: Biz from $429 Econ from $62. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Lisbon, Portugal: Econ from $563. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Anchorage, Alaska: Econ from $339. -April-June
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Charleston, South Carolina: Econ from $93. – Apr-Jun
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 $58. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Kansas City, Kansas: Biz from $395 Econ from $137. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Pedro Sula, Honduras: Biz from $712 Econ from $256. – Apr-Jun
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 $55. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Athens, Greece: Econ from $596. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Atlanta, Georgia: Biz from $18 Econ from $48. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Boise, Idaho: Econ from $154. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Denver, Colorado: Biz from $499 Econ from $58. – Apr-Jun
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
MDW > Philadelphia, Pennsylvania: Biz from $430 Econ from $68. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Savannah, Georgia: Econ from $75. – Apr-Jun
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 $251. – Apr-Jun
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 $499 Econ from $117. – Apr-Jun
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 $970 Econ from $244. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Cincinnati, Ohio: Biz from $268 Econ from $98. – May-Jul
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 $118. – Mar-May
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Houston, Texas: Econ from $92. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > San Jose, Costa Rica: Biz from $1221 Econ from $249. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Skopje, North Macedonia: Econ from $521. – 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 > Managua, Nicaragua: Biz from $817 Econ from $205. – Apr-Jun
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 $555. – Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Krakow, Poland: Econ from $531. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Athens, Greece: Econ from $512. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Marrakesh, Morocco: Econ from $516. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Budapest, Hungary: Econ from $511. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Philadelphia, Pennsylvania: Biz from $409 Econ from $58. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Dallas, Texas: Biz from $409 Econ from $48. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Santa Ana, California: Econ from $120. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Buenos Aires, Argentina: Econ from $858. – Apr-Jun (Including Summer Break)
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 $645 Econ from $172. – Apr-Jun
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…