I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Los Angeles, California: Biz from $290 Econ from $72.- Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Poznan, Poland: 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 > Algiers, Algeria: Econ from $519.- Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Newark, New Jersey: Biz from $191 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…
MDW > Orlando, Florida: Econ from $57.- Dec-Feb
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * There only…
ORD > Barcelona, Spain: Econ from $355.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Marrakesh, Morocco: Econ from $509.- Feb-Apr (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 > Managua, Nicaragua: Biz from $520 Econ from $214.- Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Houston, Texas: Biz from $286 Econ from $57.- Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Atlanta, Georgia: Biz from $249 Econ from $57.- Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Riga, Latvia: Econ from $534.- Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Krakow, Poland: Econ from $388. – Jan-Mar (Presidents day Weekend)
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Cancun, Mexico: Biz from $530 Econ from $202.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Casablanca, Morocco: Econ from $780. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Guadalajara, Mexico: Biz from $677 Econ from $301. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Diego, California: Econ from $155. – Nov-Jan (Including Thanksgiving)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Dallas, Texas: Biz from $277 Econ from $58. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Prague, Czech Republic: Econ from $447. – 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 > Pittsburgh, Pennsylvania: Biz from $287. Econ from $134. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Reno, Nevada: Econ from $130. – Nov-Jan
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
ORD > Bangkok, Thailand: Econ from $682. – Jan-Mar
* This is a “fare dump” with a few alternate dates available.
ORD > Coxen Hole, Honduras: Biz from $1424. Econ from $489. – Nov-Jan
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Thera, Greece: Econ from $674. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Francisco, California: Econ from $142. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Kinshasa, Democratic Republic of the Congo: Econ from $916. – Dec-Feb (Including MLK Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Fort Myers, Florida: Biz from $330. Econ from $73. – Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Willemstad, Curaçao: Biz from $1080. Econ from $428. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dubai, United Arab Emirates: Econ from $589. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Fort Lauderdale, Florida: Biz from $313 Econ from $61. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Baku, Azerbaijan: Econ from $859. – Dec-Feb
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Dublin, Ireland: Econ from $349. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Pedro Sula, Honduras: Biz from $503 Econ from $237. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Melbourne, Australia: Econ from $1043. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Athens, Greece: Econ from $493. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > New Orleans, Louisiana: Biz from $303 Econ from $96. – 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…
MDW > Phoenix, Arizona: Econ from $79. – Dec-Feb (Including MLK Weekend)
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Santo Domingo, Dominican Republic: Biz from $596 Econ from $287. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $347 Econ from $111. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…