Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dallas, Texas: Biz from $248 Econ from $87. – Sep-Nov (Including Fall Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Cincinnati, Ohio: Biz from $412 Econ from $143. – Oct-Dec [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 > Cancun, Mexico: Biz from $431 Econ from $238. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Punta Cana, Dominican Republic: Biz from $770 Econ from $205. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Guadalajara, Mexico: Biz from $750 Econ from $257. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Louisville, Kentucky: Biz from $307 Econ from $137. – Sep-Nov (Including Fall Break) [SOLD OUT]
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Orlando, Florida: Biz from $256 Econ from $77. – Sep-Nov (Including Fall Break) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Fort Lauderdale, Florida: Biz from $343. Econ from $92. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Willemstad, Curaçao: Biz from $1074. Econ from $350. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Pittsburgh, Pennsylvania: Biz from $287. Econ from $97. – Sep-Nov (Including Fall 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 Salvador, El Salvador: Biz from $759. Econ from $214. – Oct-Dec [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: Biz from $1257 Econ from $309. – Sep-Nov (Including Fall 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 > Mexico City, Mexico: Biz from $524 Econ from $213. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Denver, Colorado: Biz from $427 Econ from $81. – Oct-Dec [SOLD OUT]
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > New York, New York: Biz from $398 Econ from $67. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1167 Econ from $573. – Dec-Feb [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Tampa, Florida: Biz from $365 Econ from $113. – Oct-Dec [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > George Town, Cayman Islands: Biz from $616 Econ from $311. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Phoenix, Arizona: Biz from $405 Econ from $126. – Oct-Dec [SOLD OUT]
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 $185 Econ from $76. – Oct-Dec [SOLD OUT]
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 $584 Econ from $259. – Sep-Nov (Including Fall 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 > Baltimore, Maryland: Biz from $226. Econ from $91. – Oct-Dec [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 > Austin, Texas: Biz from $523. Econ from $74. – Sep-Nov [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Kingston, Jamaica: Biz from $780. Econ from $342. – Oct-Dec [SOLD OUT]
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: Biz from $329. Econ from $87. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Atlanta, Georgia: Biz from $242. Econ from $92. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Birmingham, Alabama: Biz from $387 Econ from $145. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cali, Colombia: Biz from $643 Econ from $280. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $291 Econ from $83. – Dec-Feb [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * There only appear to…
ORD > Florianopolis, Brazil: Biz from $1367 Econ from $716. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > St. Louis, Missouri: Biz from $271 Econ from $134. – Sep-Nov [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Toronto, Canada: Biz from $552 Econ from $241. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Tunis, Tunisia: Biz from $2627 Econ from $809. – Oct-Dec [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Raleigh, North Carolina: Biz from $352 Econ from $138. – Sep-Nov [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Myrtle Beach, South Carolina: Biz from $358 Econ from $133. – Sep-Nov (Including Fall 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 > Managua, Nicaragua: Biz from $1012 Econ from $234. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Miami, Florida: Biz from $234 Econ from $86.- Sep-Nov [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: Biz from $284 Econ from $58.- Sep-Nov (Including Fall 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 > Medellin, Colombia: Biz from $525 Econ from $228.- Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…