Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Raleigh, North Carolina: Biz from $398 Econ from $80. – Jul-Sep [SOLD OUT]
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
MDW > Dallas, Texas: Biz from $418 Econ from $78. – Jul-Sep [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $213. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Los Angeles, California: Biz from $516 Econ from $166. – Jul-Sep [SOLD OUT]
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 $791 Econ from $302. – Jul-Sep (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Denver, Colorado: Biz from $488 Econ from $60. – Jul-Sep [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Montego Bay, Jamaica: Biz from $962 Econ from $306. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Atlanta, Georgia: Biz from $398 Econ from $48. – Jul-Sep [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Greenville, South Carolina: Biz from $408 Econ from $168. – Jul-Sep [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Madison, Wisconsin: Biz from $298 Econ from $138. – Jul-Sep (Including Summer 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 > Managua, Nicaragua: Biz from $1147 Econ from $324. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Houston, Texas: Econ from $119. – Jul-Sep (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Liberia, Costa Rica: Econ from $322. – Jul-Sep [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Boston, Massachusetts: Biz from $438 Econ from $162. – Jul-Sep [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Santo Domingo, Dominican Republic: Biz from $940 Econ from $268. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Little Rock, Arkansas: Econ from $168. – Jul-Sep [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Washington, DC: Econ from $118. – Jul-Sep [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Punta Cana, Dominican Republic: Biz from $927 Econ from $239. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Jose, Costa Rica: Biz from $1039 Econ from $276. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $368 Econ from $128. – Jul-Sep [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is an airline…
MDW > Phoenix, Arizona: Econ from $120. – Jul-Sep (Including Summer Break) [SOLD OUT]
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Columbia, South Carolina: Econ from $168. – Jul-Sep [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > St. Louis, Missouri: Econ from $151. – Jul-Sep [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Nadi, Fiji: Econ from $846. – Aug-Oct (Including Labor Day) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Huntsville, Alabama: Biz from $467 Econ from $168. – Jul-Sep [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 > Christiansted, U.S. Virgin Islands: Biz from $1234 Econ from $294. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Dallas, Texas: Biz from $557 Econ from $80. – Jul-Sep [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Raleigh, North Carolina: Econ from $80. – Jul-Sep [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Montego Bay, Jamaica: Biz from $990 Econ from $334. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Philadelphia, Pennsylvania: Econ from $80. – Jul-Sep [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Burlington, Kentucky: Econ from $121. – Jul-Sep [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Jose, Costa Rica: Econ from $279. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Milwaukee, Wisconsin: Biz from $396 Econ from $138. – Jul-Sep (Including Summer 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…
MDW > San Juan, Puerto Rico: Econ from $158. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Buenos Aires, Argentina: Econ from $806. – Aug-Oct [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Asheville, North Carolina: Econ from $75. – Jul-Sep [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Jose, Costa Rica: Econ from $328. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Juan, Puerto Rico: Econ from $138. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Econ from $152. – Jul-Sep [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…