Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kansas City, Kansas: Biz from $281 Econ from $91. – Jul-Sep
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Prague, Czech Republic: Econ from $531. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
(Including Labor Day) ORD > Cozumel, Mexico: Biz from $635 Econ from $262. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Willemstad, Curaçao: Econ from $651. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Riga, Latvia: Econ from $488. – Aug-Oct (Including Labor Day)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Mykonos, Greece: Econ from $763. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Mykonos, Greece: Econ from $760. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Nadi, Fiji: Econ from $1028. – Aug-Oct (Including Labor Day)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Mykonos, Greece: Econ from $673. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Thera, Greece: Econ from $620. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Philadelphia, Pennsylvania: Biz from $418 Econ from $68. – 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 > Denver, Colorado: Biz from $408 Econ from $94. – Jul-Sep [SOLD OUT]
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
MDW > Kansas City, Kansas: Biz from $499 Econ from $135. – Aug-Oct (Including Labor Day) [SOLD OUT]q
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Zacatecas, Mexico: Econ from $262. – Aug-Oct (Including Labor Day) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Miami, Florida: Econ from $68. – 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 > Atlanta, Georgia: Biz from $378 Econ from $36. – 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 > Punta Cana, Dominican Republic: Biz from $941 Econ from $240. – 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, California: Econ from $137. – 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 > Atlantic City, New Jersey: Biz from $630 Econ from $92. – Aug-Oct (Including Labor Day) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Charlotte, North Carolina: Econ from $92. – 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 > Nassau, The Bahamas: Econ from $256. – 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 > Fort Lauderdale, Florida: Econ from $83. – 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 > Dallas, Texas: Biz from $418 Econ from $66. – 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 > Montego Bay, Jamaica: Biz from $1004 Econ from $260. – 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 Francisco, California: Econ from $121. – Jul-Sep [SOLD OUT]
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
MDW > Sacramento, California: Econ from $151. – 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 > Cincinnati, Ohio: Biz from $420 Econ from $136. – 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 > Christiansted, U.S. Virgin Islands: Econ from $278. – 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 > Asheville, North Carolina: Econ from $85. – 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 > San Juan, Puerto Rico: Biz from $692 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.…
MDW > Atlanta, Georgia: Biz from $496 Econ from $38. – 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 > Managua, Nicaragua: Biz from $1048 Econ from $243. – 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 > Lima, Peru: Biz from $1219 Econ from $345. – Jul-Sep [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Diego, California: Econ from $150. – 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 > Baltimore, Maryland: Econ from $77. – 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 > Austin, Texas: Econ from $154. – 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 > Fort Myers, Florida: Econ from $106. – 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 > Savannah, Georgia: Biz from $587 Econ from $131. – 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 > 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…