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 > 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.…
ORD > Philadelphia, Pennsylvania: Biz from $357 Econ from $80.- Oct-Dec [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Dallas, Texas: Biz from $211 Econ from $90.- Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Riga, Latvia: Biz from $2203 Econ from $467.- 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 > Cancun, Mexico: Biz from $376 Econ from $201.- 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 > Cincinnati, Ohio: Biz from $418 Econ from $144.- 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 > New Delhi, India: Econ from $661.- Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cluj Napoca, Romania: Econ from $512.- Oct-Dec
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
MDW > Boston, Massachusetts: Econ from $137.- 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 > Nairobi, Kenya: Econ from $813.- Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Poznan, Poland: Econ from $416.- 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 > Guadalajara, Mexico: Biz from $919 Econ from $226.- Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Kansas City, Kansas: Econ from $144.-Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Zagreb, Croatia: Econ from $608.- Oct-Dec (Including Fall Break) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Colombo, Sri Lanka: Econ from $687.- 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 > Louisville, Kentucky: Econ from $97.- 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 > Orlando, Florida: Biz from $282 Econ from $86.- Sep-Nov [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * There only…
ORD > Guatemala City, Guatemala: Biz from $508 Econ from $196.- 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 > Prague, Czech Republic: Econ from $398.- Oct-Dec (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 > Chennai, India: Econ from $764.- 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 > Lisbon, Portugal: Econ from $389.- Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > San Diego, California: Econ from $154. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Jacksonville, Florida: Econ from $142. – Aug-Oct [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Kathmandu, Nepal: Econ from $744. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Palma de Mallorca, Spain: Econ from $414. – 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: Econ from $238. – 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…
ORD > Denver, Colorado: Biz from $412 Econ from $104. – Sep-Nov [SOLD OUT]
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…