Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Pedro Sula, Honduras: Biz from $905 Econ from $309. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Boston, Massachusetts: Biz from $383 Econ from $98. – Nov-Jan
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
MDW > Ontario, California: Econ from $88. – Nov-Jan
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 $715. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Oranjestad, Aruba: Biz from $1117 Econ from $218. – Nov-Jan
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Charleston, South Carolina: Econ from $97. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Asheville, North Carolina: Biz from $408 Econ from $78. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Hartford, Connecticut: Biz from $5878 Econ from $118. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Palanga, Lithuania: Econ from $507. – Dec-Feb (Including Winter Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Los Angeles, California: Biz from $478 Econ from $85. – Nov-Jan
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > San Juan, Puerto Rico: Biz from $806 Econ from $101 . – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Abidjan, Ivory Coast: Econ from $934. – Nov-Jan (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > San Antonio, Texas: Econ from $113. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Cancun, Mexico: Biz from $760 Econ from $166. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Charlotte, North Carolina: Biz from $397 Econ from $55. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Sacramento, California: Econ from $110. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Liberia, Costa Rica: Econ from $223. – Nov-Jan
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > New York, New York: Biz from $408 Econ from $87. – Nov-Jan
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Houston, Texas: Econ from $82. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Fort Lauderdale, Florida:Econ from $64. – Nov-Jan
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $226. – Nov-Jan
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 $88. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Philadelphia, Pennsylvania: Biz from $408 Econ from $38. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Salt Lake City, Utah: Biz from $402 Econ from $88. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Portland, Oregon: Econ from $118. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Salzburg, Austria: Econ from $591. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Las Vegas, Nevada: Econ from $58. – Nov-Jan
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…
ORD > Belgrade, Serbia: Econ from $601. – 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…
MDW > Phoenix, Arizona: Econ from $38. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Tirana, Albania: Biz from $2630 Econ from $621. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Brasilia, Brazil: Biz from $2811 Econ from $699. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Francisco, California: Econ from $58. – Nov-Jan
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
MDW > Los Angeles, California: Econ from $106. – Nov-Jan
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
MDW > Asheville, North Carolina: Biz from $431 Econ from $74. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Charlotte, North Carolina: Biz from $377 Econ from $56. – Nov-Jan
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 $35. – Nov-Jan
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Male, Maldives: Econ from $889. – 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 > Abu Dhabi, United Arab Emirates: Econ from $680. – 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 > Marrakesh, Morocco: Econ from $639. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…