Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Louisville, Kentucky: Biz from $329 Econ from $166.- Dec-Feb (Including MLK Weekend)
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Asheville, North Carolina: Econ from $166.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New Delhi, India: Econ from $661.- Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Poznan, Poland: Econ from $491.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belize City, Belize: Biz from $521 Econ from $281.- Jan-Mar
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Cincinnati, Ohio: Biz from $383 Econ from $135.- Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > San Diego, California: Econ from $151.- 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 > Cairo, Egypt: Econ from $642.- Feb-Apr (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 > Mykonos, Greece: Econ from $639.- Jul-Sep
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Montego Bay, Jamaica: Biz from $513 Econ from $276.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Philadelphia, Pennsylvania: Biz from $288 Econ from $61.- Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Baltimore, Maryland: Biz from $285 Econ from $57.- Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Bucharest, Romania: Econ from $577.- Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Riga, Latvia: Econ from $460.- Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cancun, Mexico: Biz from $386 Econ from $198.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Boston, Massachusetts: Biz from $289 Econ from $127.- Dec-Feb
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
MDW > Dallas, Texas: Biz from $487 Econ from $62.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Malaga, Spain: Econ from $376.- Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Belgrade, Serbia: Econ from $516.- Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > George Town, Cayman Islands: Biz from $524 Econ from $248.- Dec-Feb
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 $58.- Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Houston, Texas: Biz from $261 Econ from $72.- 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 > Chennai, India: Econ from $604.- 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 > Krakow, Poland: Econ from $390.- 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 > Managua, Nicaragua: Biz from $436 Econ from $211.- 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 > Phoenix, Arizona: Econ from $57.- Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Atlanta, Georgia: Biz from $567 Econ from $48.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Athens, Greece: Econ from $452.- Jan-Mar
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 $549.- Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Pedro Sula, Honduras: Biz from $460 Econ from $229.- Dec-Feb
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 $351 Econ from $94.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Newark, New Jersey: Econ from $53. – Dec-Feb (Including MLK Weekend)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Barcelona, Spain: Econ from $352.
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Marrakesh, Morocco: Econ from $510.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Salvador, El Salvador: Biz from $446 Econ from $216.- Jan-Mar
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 $114. – Apr-Jun (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Tunis, Tunisia: Econ from $849. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Jacksonville, Florida: Biz from $509. Econ from $162. – 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 > Prague, Czech Republic: Econ from $408. – 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…