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
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > San Antonio, Texas: Econ from $147. – 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 > 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 > Casablanca, Morocco: Econ from $478. – Oct-Dec
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
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Bali, Indonesia: Econ from $687. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Lisbon, Portugal: Econ from $461. – Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Palma de Mallorca, Spain: Econ from $422. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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…
MDW > Jacksonville, Florida: Econ from $144. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Dubai, United Arab Emirates: Econ from $553. – Oct-Dec (Including Thanksgiving)
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
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,…
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 > Gdansk, Poland: Econ from $391. – Oct-Dec (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Algiers, Algeria: Econ from $580. – Nov-Jan (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Tokyo, Japan: Econ from $741. – Apr-Jun
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Athens, Greece: Econ from $472. – 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…
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…
ORD > Nashville, Tennessee: Biz from $185 Econ from $76. – Oct-Dec
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 > Cape Town, South Africa: Econ from $1009. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Baltimore, Maryland: Biz from $226. Econ from $91. – 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 > 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…
MDW > San Jose, Costa Rica: Econ from $344. – Oct-Dec (Including Thanksgiving)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Krakow, Poland: Econ from $526. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Abu Dhabi, United Arab Emirates: Econ from $569. – 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 > 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 > Berlin, Germany: Econ from $435. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cali, Colombia: Biz from $643 Econ from $280. – 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 $291 Econ from $83. – Dec-Feb
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 > Portland, Oregon: Econ from $141. – 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…
MDW > Toronto, Canada: Biz from $552 Econ from $241. – Oct-Dec (Including Thanksgiving)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Bucharest, Romania: Econ from $600. – Oct-Dec
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
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…