Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Raleigh, North Carolina: Econ from $80. – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Tallinn, Estonia: Econ from $404. – Jul-Sep [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $214. – 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.…
ORD > Miami, Florida: Econ from $65. – 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 > New Orleans, Louisiana: Biz from $418 Econ from $58. – 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 > Cancun, Mexico: Biz from $540 Econ from $167. – 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 > Atlantic City, New Jersey: Biz from $622 Econ from $126. – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Philadelphia, Pennsylvania: Biz from $414 Econ from $80. – 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 > Cali, Colombia: 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 > Boston, Massachusetts: Biz from $408 Econ from $119. – Jul-Sep [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
MDW > Knoxville, Tennessee: Econ from $76. – 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…
ORD > Nashville, Tennessee: Biz from $390 Econ from $95. – Jul-Sep [SOLD OUT]
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > San Jose, Costa Rica: Biz from $1039 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.…
MDW > San Francisco, California: Econ from $131. – Jul-Sep [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Fort Lauderdale, Florida: Econ from $71. – Aug-Oct (Including Labor Day) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Charlotte, North Carolina: Econ from $87. – 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…
ORD > Los Angeles, California: Econ from $120. – Jul-Sep [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Fortaleza, Brazil: Econ from $696. – Jul-Sep [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Lexington, Kentucky: Biz from $328 Econ from $148. – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Sacramento, California: Econ from $161. – 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 > Atlanta, Georgia: Biz from $398 Econ from $45. – Jul-Sep (Including Summer Break) [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 Juan, Puerto Rico: Biz from $682 Econ from $159. – 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.…
ORD > Greenville, South Carolina: Biz from $408 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 > Las Vegas, Nevada: Econ from $120. – Jul-Sep [SOLD OUT]
Vegas Baby! * This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but…
ORD > Baltimore, Maryland: Econ from $98.- 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…
ORD > Houston, Texas: Econ from $96. – Aug-Oct (Including Labor Day) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Managua, Nicaragua: Biz from $1147 Econ from $291. – 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 > Salt Lake City, Utah: Econ from $159. – 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 > Punta Cana, Dominican Republic: 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 > Chattanooga, Tennessee: Biz from $328 Econ from $148. – 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 > Ontario, California: Econ from $146. – 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 > Miami, Florida: Econ from $92. – 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 > Cincinnati, Ohio: Biz from $368 Econ from $170. – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Monterrey, Mexico: Biz from $378 Econ from $230. – Aug-Oct (Including Labor Day) [SOLD OUT] [SOLD OUT]
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.…