Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Los Angeles, California: Biz from $508 Econ from $106. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Christiansted, U.S. Virgin Islands: Biz from $983 Econ from $235. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Asheville, North Carolina: Econ from $78. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Hartford, Connecticut: Biz from $597 Econ from $108. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Casablanca, Morocco: Econ from $485. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > San Juan, Puerto Rico: Biz from $871 Econ from $115. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Las Vegas, Nevada: Econ from $73. – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > New York, New York: Biz from $444 Econ from $86. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Algiers, Algeria: Econ from $463. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Male, Maldives: Econ from $843. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Richmond, Virginia: Biz from $468 Econ from $121. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Seattle, Washington: Econ from $129. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Larnaca, Cyprus: Econ from $461. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Miami, Florida: 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 > Belgrade, Serbia: Econ from $608. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > San Jose, Costa Rica: Biz from $1227 Econ from $233. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Reno, Nevada: Econ from $141. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Sacramento, California: Econ from $111. – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $220. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Portland, Oregon: Econ from $158. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Dallas, Texas: Biz from $503 Econ from $37. – 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 > Abu Dhabi, United Arab Emirates: Econ from $641. – 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 > Atlantic City, New Jersey: Biz from $610 Econ from $111. – Nov-Jan
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 $577. – 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 > Fort Lauderdale, Florida: Econ from $65. – Nov-Jan
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
MDW > San Diego, California: Econ from $88. – Nov-Jan
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Denver, Colorado: Biz from $557 Econ from $38. – Nov-Jan
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Cincinnati, Ohio: Biz from $250 Econ from $114. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Sibiu, Romania: Econ from $763. – Nov-Jan
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 $378 Econ from $38. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Kingston, Jamaica: Biz from $866 Econ from $275. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Salt Lake City, Utah: 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…
MDW > Atlanta, Georgia: Biz from $338 Econ from $37. – 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 > Managua, Nicaragua: Biz from $1140 Econ from $198. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Santa Ana, 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…
ORD > Phoenix, Arizona: Econ from $71. – Nov-Jan
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…