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 > Montego Bay, Jamaica: Biz from $610 Econ from $298.- Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > St. Louis, Missouri: Econ from $137. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Las Vegas, Nevada: Biz from $320. Econ from $54. – Dec-Feb
Vegas Baby! * There only appear to be a few seats at this price and availability is spotty. It will…
MDW > Luqa, Malta: Econ from $544. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Saint Thomas Island, U.S. Virgin Islands: Econ from $275. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Newark, New Jersey: Econ from $53.- Nov-Jan
Have you ever booked a cruise only to find out that the flight to get there was going to be…
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…
ORD > Fort Lauderdale, Florida: Biz from $295 Econ from $66.- Nov-Jan
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
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…
ORD > Charlotte, North Carolina: Biz from $231 Econ from $61.- 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 > Dublin, Ireland: Econ from $345.- Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: Econ from $444.- Oct-Dec (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 > San Pedro Sula, Honduras: Biz from $489 Econ from $243.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Athens, Greece: Econ from $492. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belize City, Belize: Econ from $363. – Dec-Feb (Including Winter Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…