Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Colombo, Sri Lanka: Econ from $735. – Mar-May (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 > Boston, Massachusetts: Biz from $343 Econ from $110.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Montego Bay, Jamaica: Biz from $566 Econ from $299.- Nov-Jan (Including Winter 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 > 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 > 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 > Houston, Texas: Biz from $286 Econ from $57.- Dec-Feb (Including MLK Weekend) [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 > Atlanta, Georgia: Biz from $249 Econ from $57.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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…
MDW > San Diego, California: Econ from $155. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
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) [SOLD OUT]
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) [SOLD OUT]
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) [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 > 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 > New Orleans, Louisiana: Biz from $303 Econ from $96. – Dec-Feb (Including MLK Weekend) [SOLD OUT]
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) [SOLD OUT]
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Belgrade, Serbia: Econ from $485. – 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 > 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 > Berlin, Germany: Econ from $434. – Jan-Mar (Presidents day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cairo, Egypt: Econ from $588. – 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 > Raleigh, North Carolina: Econ from $83. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
ORD > Nashville, Tennessee: Biz from $267 Econ from $60.- Nov-Jan (Including Thanksgiving) [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 $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.…
MDW > Knoxville, Tennessee: Econ from $111. – Oct-Dec (Including Thanksgiving) [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 > 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 > 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) [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
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) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cincinnati, Ohio: Biz from $397. Econ from $130. – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dallas, Texas: Biz from $226 Econ from $53.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cancun, Mexico: Biz from $501 Econ from $187.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
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) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Orlando, Florida: Econ from $54.- Dec-Feb (Including MLK Weekend) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
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 > Budapest, Hungary: Econ from $444.- Oct-Dec (Including Thanksgiving) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Belize City, Belize: Econ from $363. – Dec-Feb (Including Winter Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Asheville, North Carolina: Biz from $412 Econ from $84. – Oct-Dec [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…