Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Porto, Portugal: Econ from $425. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Antonio, Texas: Econ from $148. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Oranjestad, Aruba: Biz from $554 Econ from $247.- Nov-Jan
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Los Angeles, California: Biz from $587 Econ from $62.- Nov-Jan
Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…
ORD > Baltimore, Maryland: Biz from $248 Econ from $53.- Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Toronto, Canada: Biz from $448 Econ from $135.- Feb-Apr (Including Spring Break)
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 $179. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Knoxville, Tennessee: Econ from $111. – Oct-Dec (Including Thanksgiving)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Atlanta, Georgia: Biz from $537 Econ from $53.- Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > St. Louis, Missouri: Econ from $137. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cincinnati, Ohio: Biz from $397. Econ from $130. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Jacksonville, Florida: Biz from $547. Econ from $143. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Las Vegas, Nevada: Biz from $320. Econ from $54. – Dec-Feb
Vegas Baby! * There only appear to be a few seats at this price and availability is spotty. It will…
MDW > Newark, New Jersey: Econ from $53.- Nov-Jan
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Cancun, Mexico: Biz from $501 Econ from $187.- 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 > Managua, Nicaragua: Biz from $639 Econ from $262.- Nov-Jan
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 $54.- Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
MDW > Phoenix, Arizona: Econ from $54.- Dec-Feb
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Guadalajara, Mexico: Biz from $645 Econ from $211.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Prague, Czech Republic: Econ from $385.- Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > New Orleans, Louisiana: Biz from $195 Econ from $74.- Oct-Dec
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: Biz from $231 Econ from $61.- Oct-Dec
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Asheville, North Carolina: Biz from $412 Econ from $84. – Oct-Dec
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > New York, New York: Biz from $185 Econ from $58. – Oct-Dec (Including Thanksgiving)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Reno, Nevada: Biz from $401. Econ from $137. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Denver, Colorado: Biz from $428. Econ from $75. – Nov-Jan
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Santo Domingo, Dominican Republic: Biz from $521. Econ from $292. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Nashville, Tennessee: Econ from $145. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Ontario, California: Econ from $133. – Oct-Dec
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 $661 Econ from $221. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Austin, Texas: Biz from $296 Econ from $109. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Tampa, Florida: Biz from $298 Econ from $76. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Baltimore, Maryland: Biz from $304 Econ from $78. – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Los Angeles, California: Biz from $358 Econ from $75. – Oct-Dec
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Washington, DC: Econ from $106. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Toronto, Canada: Biz from $550 Econ from $230. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Minneapolis, Minnesota: Biz from $287 Econ from $78. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Barranquilla, Colombia: Biz from $499 Econ from $318. – Nov-Jan
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: Econ from $117. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…