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 > 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 > 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 > 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…
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 > 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…
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)
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)
* 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
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Tampa, Florida: Biz from $298 Econ from $76. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Belgrade, Serbia: Econ from $504. – Mar-May (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Baltimore, Maryland: Biz from $304 Econ from $78. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Berlin, Germany: Econ from $439. – Oct-Dec (Including Thanksgiving)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Male, Maldives: Econ from $950. – 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…
MDW > Toronto, Canada: Biz from $550 Econ from $230. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dhaka, Bangladesh: Econ from $780. – Nov-Jan (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 > Malaga, Spain: Econ from $411. – Nov-Jan (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Philadelphia, Pennsylvania: Biz from $322 Econ from $106. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Rabat, Morocco: Econ from $529. – Nov-Jan (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Hong Kong, Hong Kong: Econ from $710. – Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Simpson Bay, St. Maarten: Econ from $375. – Oct-Dec (Including Thanksgiving)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Francisco, California: Econ from $128. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cluj Napoca, Romania: Econ from $486. – Jan-Mar (Presidents day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Algiers, Algeria: Econ from $539. – Nov-Jan (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 > Cincinnati, Ohio: Biz from $365 Econ from $108. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Poznan, Poland: Econ from $448. – Oct-Dec (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Prague, Czech Republic: Econ from $401. – Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Louisville, Kentucky: Biz from $320 Econ from $94. – Oct-Dec (Including Thanksgiving)
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Guadalajara, Mexico: Biz from $771 Econ from $202. – 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 > Phu Quoc, Vietnam: Econ from $992. – Feb-Apr (Including Spring Break)
Do you like Vietnamese Pho? Here is a recipe my childhood friend Hien taught me. * This is an airline…
ORD > Charlotte, North Carolina: Biz from $285 Econ from $87. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Pittsburgh, Pennsylvania: Biz from $344 Econ from $103. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Dubai, United Arab Emirates: Econ from $741. – 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 > Palma de Mallorca, Spain: Econ from $402. – 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 $219. Econ from $97. – Sep-Nov (Including Fall Break) [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 > Georgetown, Guyana: Biz from $1258. Econ from $439. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…