Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > New York, New York: Biz from $191 Econ from $78. – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Denver, Colorado: Biz from $423 Econ from $74. – Oct-Dec
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
MDW > Tampa, Florida: Biz from $368 Econ from $119. – 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 > George Town, Cayman Islands: Biz from $619 Econ from $320. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Nashville, Tennessee: Biz from $206 Econ from $68. – 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,…
MDW > San Jose, Costa Rica: Biz from $702 Econ from $326. – Oct-Dec
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 $539 Econ from $131. – 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 > Austin, Texas: Biz from $346 Econ from $117. – Nov-Jan
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Cali, Colombia: Biz from $833 Econ from $287. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Atlanta, Georgia: Biz from $497 Econ from $65.- Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Montego Bay, Jamaica: Biz from $535 Econ from $266.- 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.…
MDW > Toronto, Canada: Biz from $534. Econ from $227. – Oct-Dec
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 $287. Econ from $88. – Oct-Dec (Including Thanksgiving)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Raleigh, North Carolina: Biz from $320. Econ from $102. – Sep-Nov (Including Fall Break) [SOLD OUT]
My brother sent my Nephew to visit us for a weekend thanks to cheap fares to Raleigh. Watch this video…
ORD > Boston, Massachusetts: Biz from $369. Econ from $117. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Barranquilla, Colombia: Biz from $497. Econ from $273. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $968. Econ from $346. – Nov-Jan
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Philadelphia, Pennsylvania: Biz from $256. Econ from $90. – 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 > Houston, Texas: Biz from $206. Econ from $90. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Pedro Sula, Honduras: Biz from $1259. Econ from $267. – Oct-Dec
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
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)
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
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
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
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)
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
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
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
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
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
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…