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 [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Krakow, Poland: Econ from $490.- 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 > 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.…
ORD > Riga, Latvia: Econ from $439.- 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 > Washington, DC: Econ from $104. – Oct-Dec [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Toronto, Canada: Biz from $534. Econ from $227. – 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 $287. Econ from $88. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Abu Dhabi, United Arab Emirates: Econ from $796. – 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…
ORD > Malaga, Spain: Econ from $436. – Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Boston, Massachusetts: Biz from $369. Econ from $117. – 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 > Barranquilla, Colombia: Biz from $497. Econ from $273. – 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 > Bucharest, Romania: Econ from $520. – Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Palanga, Lithuania: Econ from $428. – 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…
ORD > Barcelona, Spain: Econ from $360. – Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Rabat, Morocco: Econ from $556. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > San Pedro Sula, Honduras: Biz from $1259. Econ from $267. – 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 > 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 > Cluj Napoca, Romania: Econ from $518. – 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 > Burbank, California: Econ from $143. – 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…
MDW > Knoxville, Tennessee: Econ from $108. – 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 > Chennai, India: Econ from $751. – 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…
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 > Prague, Czech Republic: Econ from $432. – Oct-Dec (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Auckland, New Zealand: Econ from $1068. – 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…
ORD > Madrid, Spain: Econ from $377. – Oct-Dec [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
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 > 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 > Casablanca, Morocco: Econ from $478. – 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 > San Diego, California: Econ from $146. – 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 > Asheville, North Carolina: Econ from $81. – 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 > Bali, Indonesia: Econ from $687. – 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…
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…
MDW > Jacksonville, Florida: Econ from $144. – 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…
MDW > Newark, New Jersey: Econ from $61. – Oct-Dec [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Dubai, United Arab Emirates: Econ from $553. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Phu Quoc, Vietnam: Econ from $845. – 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 > 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 > Ontario, California: Econ from $148. – 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…