Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Antonio, Texas: Econ from $126. – May-Jul (Including Summer Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Guatemala City, Guatemala: Econ from $185. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Pittsburgh, Pennsylvania: Econ from $111. – May-Jul (Including Summer Break)
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 $118. – May-Jul (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Portland, Maine: Econ from $98. – Jun-Aug (Including Fourth of July and Summer Break)
I rarely post trips to Portland because they are typically so expensive. Snatch this one up before someone else does.…
MDW > Toronto, Canada: Biz from $676 Econ from $267. – May-Jul (Including Summer Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cartagena, Colombia: Econ from $228. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Knoxville, Tennessee: Econ from $83. – May-Jul (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Nashville, Tennessee: Biz from $417 Econ from $67. – May-Jul (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 > Boston, Massachusetts: Biz from $417 Econ from $74. – May-Jul (Including Summer Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Cincinnati, Ohio: Biz from $264 Econ from $119. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Piarco, Trinidad and Tobago: Biz from $899 Econ from $427. – May-Jul (Including Summer Break)
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 $107. – May-Jul (Including Summer Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Knoxville, Tennessee: Econ from $79. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
(Including Summer Break) ORD > Belo Horizonte, Brazil: Econ from $643. – May-Jul
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Nashville, Tennessee: Biz from $328. Econ from $48. – May-Jul (Including Summer Break)
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
MDW > Christiansted, U.S. Virgin Islands: Econ from $342. – May-Jul (Including Summer Break)
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. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Atlanta, Georgia: Biz from $429 Econ from $53. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Fort Lauderdale, Florida: Econ from $99. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Atlanta, Georgia: Biz from $428 Econ from $48. – Jun-Aug (Including Fourth of July and Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Baltimore, Maryland: Econ from $90. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Savannah, Georgia: Econ from $72. – Jun-Aug (Including Fourth of July and Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Houston, Texas: Econ from $143. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cancun, Mexico: Biz from $884 Econ from $212. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New Orleans, Louisiana: Econ from $106. – May-Jul (Including Summer Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Atlanta, Georgia: Biz from $398 Econ from $73. – Jun-Aug (Including Fourth of July and Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Washington, DC: Econ from $121. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Fort Lauderdale, Florida: Econ from $117. – May-Jul (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Salvador, El Salvador: Biz from $1061 Econ from $313. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Liberia, Costa Rica: Econ from $335. – May-Jul (Including Summer Break) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Miami, Florida: Econ from $85. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cincinnati, Ohio: Biz from $419 Econ from $156. – Jun-Aug (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Savannah, Georgia: Econ from $49. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > San Antonio, Texas: Econ from $155. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cancun, Mexico: Biz from $701 Econ from $209. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Norfolk, Virginia: Econ from $135. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Houston, Texas: Econ from $116. – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Las Vegas, Nevada: Econ from $140. – May-Jul (Including Summer Break) [SOLD OUT]
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…