Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Gdansk, Poland: Econ from $423. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Sharjah, United Arab Emirates: Econ from $792. – Sep-Nov [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Willemstad, Curaçao: Biz from $1378 Econ from $494. – 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 > Ljubljana, Slovenia: Econ from $558. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Mexico City, Mexico: Econ from $218. – Oct-Dec (Including Fall Break) [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 > Heraklion, Greece: Econ from $676. – Sep-Nov [SOLD OUT]
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Mexico City, Mexico: Econ from $216. – Sep-Nov (Including Fall Break) [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
MDW > Morelia, Mexico: Econ from $233. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Pointe La Rue, Seychelles: Econ from $1082. – Sep-Nov (Including Fall Break) [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 > Guadalajara, Mexico: Econ from $206. – Oct-Dec (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 > Pointe La Rue, Seychelles: Econ from $1055. – Sep-Nov [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Palanga, Lithuania: Econ from $557. – Jul-Sep [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Mexico City, Mexico: Econ from $158. – Oct-Dec (Including Fall Break) [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 > Krakow, Poland: Econ from $411. – Sep-Nov [SOLD OUT]
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Guadalajara, Mexico: Biz from $855 Econ from $204. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Marrakesh, Morocco: Econ from $509. – Sep-Nov [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 > Leon, Mexico: Econ from $184. – 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 > Mexico City, Mexico: Econ from $180. – Oct-Dec [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 > Krakow, Poland: Econ from $398. – Sep-Nov [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubai, United Arab Emirates: Econ from $700. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Myrtle Beach, South Carolina: Econ from $85. – 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 > Oakland, California: Econ from $124. – 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…
MDW > Phoenix, Arizona: Econ from $159. – 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 > Saint Thomas Island, U.S. Virgin Islands: Econ from $292. – 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 > Houston, Texas: Econ from $78. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Reno, Nevada: Econ from $164. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Minneapolis, Minnesota: Biz from $362 Econ from $122. – Sep-Nov [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is an airline…
ORD > Anchorage, Alaska: Biz from $1,056 Econ from $320. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Myrtle Beach, South Carolina: Econ from $97. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > New Orleans, Louisiana: Econ from $49. – 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 > Lima, Peru: Econ from $414. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Baltimore, Maryland: Econ from $126. – Sep-Nov (Including Fall 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 > New York, New York: Biz from $412 Econ from $118. [SOLD OUT]
– Sep-Nov (Including Fall Break) Have you ever booked a cruise only to find out that the flight to get…
MDW > Cincinnati, Ohio: Biz from $378 Econ from $142. – Oct-Dec (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…
MDW > Boston, Massachusetts: Biz from $525 Econ from $158. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Santa Ana, California: Econ from $139. – 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…
MDW > Beirut, Lebanon: Biz from $2,237 Econ from $697. – Oct-Dec (Including Fall Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Kansas City, Kansas: Biz from $414 Econ from $156. – Sep-Nov (Including Fall Break) [SOLD OUT]
Ribs anyone? * This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but…
MDW > Orlando, Florida: Econ from $85. – 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…