For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Malaga, Spain: Econ from $374. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Nashville, Tennessee: Biz from $267 Econ from $60.- Nov-Jan (Including Thanksgiving)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Phuket City, Thailand: Econ from $562.- Mar-May
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Los Angeles, California: Biz from $587 Econ from $62.- Nov-Jan
Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…
ORD > Baltimore, Maryland: Biz from $248 Econ from $53.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Bucharest, Romania: Econ from $485.- Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Algiers, Algeria: Econ from $553.- Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Toronto, Canada: Biz from $448 Econ from $135.- Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Portland, Oregon: Econ from $179. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Colombo, Sri Lanka: Econ from $774. – Mar-May (Including Spring Break)
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 $356. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cluj Napoca, Romania: Econ from $518. – Feb-Apr (Including Spring Break)
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Boston, Massachusetts: Biz from $425 Econ from $117. – Dec-Feb (Including Winter Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Miami, Florida: Biz from $247 Econ from $84. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Sao Paulo, Brazil: Biz from $1877 Econ from $428. – Nov-Jan
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Houston, Texas: Biz from $191 Econ from $80.- Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Atlanta, Georgia: Biz from $537 Econ from $53.- Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Kuala Lumpur, Malaysia: Econ from $649.- Jan-Mar (Presidents day Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Krakow, Poland: Econ from $389.- Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Gdansk, Poland: Econ from $495. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cincinnati, Ohio: Biz from $397. Econ from $130. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Guatemala City, Guatemala: Biz from $436. Econ from $218. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Tunis, Tunisia: Econ from $568. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Jacksonville, Florida: Biz from $547. Econ from $143. – Nov-Jan
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 $764. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Dallas, Texas: Biz from $226 Econ from $53.- Oct-Dec (Including Thanksgiving)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Poznan, Poland: Econ from $492.- Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Riga, Latvia: Econ from $415.- Apr-Jun
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 $501 Econ from $187.- Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Diego, California: Econ from $103.- Dec-Feb (Including MLK Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Casablanca, Morocco: Econ from $539.- Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Madrid, Spain: Econ from $323.- Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Managua, Nicaragua: Biz from $639 Econ from $262.- Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Orlando, Florida: Econ from $54.- Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
MDW > Phoenix, Arizona: Econ from $54.- Dec-Feb
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Almaty, Kazakhstan: Econ from $821.- 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 > Guadalajara, Mexico: Biz from $645 Econ from $211.- Jan-Mar
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 $385.- Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > New Orleans, Louisiana: Biz from $195 Econ from $74.- Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…