Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Auckland, New Zealand: Econ from $1019. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Poznan, Poland: Econ from $448. – Oct-Dec (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Colombo, Sri Lanka: Econ from $733. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Portland, Oregon: Econ from $158. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Louisville, Kentucky: Biz from $320 Econ from $94. – Oct-Dec (Including Thanksgiving)
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Casablanca, Morocco: Econ from $528. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Willemstad, Curaçao: Biz from $1399 Econ from $454. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Fort Lauderdale, Florida: Biz from $327 Econ from $105. – Oct-Dec
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Charlotte, North Carolina: Biz from $285 Econ from $87. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > San Antonio, Texas: Econ from $154. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Pittsburgh, Pennsylvania: Biz from $344 Econ from $103. – 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…
MDW > Dubai, United Arab Emirates: Econ from $741. – Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Managua, Nicaragua: Biz from $774 Econ from $234. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Diego, California: Econ from $153. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Okinawa, Japan: Econ from $961. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Georgetown, Guyana: Biz from $1258. Econ from $439. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Asheville, North Carolina: Econ from $80. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Newark, New Jersey: Econ from $58. – Oct-Dec
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Abuja, Nigeria: Biz from $3217. Econ from $790. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Denver, Colorado: Biz from $423 Econ from $74. – Oct-Dec
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Ontario, California: Econ from $146. – Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Tokyo, Japan: Econ from $680. – Oct-Dec [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 > Cape Town, South Africa: Econ from $1000. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Heraklion, Greece: Econ from $642. – Oct-Dec
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Phoenix, Arizona: Econ from $99. – Oct-Dec [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > San Jose, Costa Rica: Biz from $702 Econ from $326. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Berlin, Germany: Econ from $438. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Male, Maldives: Econ from $942. – Oct-Dec [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cali, Colombia: Biz from $833 Econ from $287. – Oct-Dec
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 $497 Econ from $65.- Oct-Dec
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Krakow, Poland: Econ from $490.- Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Montego Bay, Jamaica: Biz from $535 Econ from $266.- Oct-Dec [SOLD OUT]
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 $439.- Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Washington, DC: Econ from $104. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Toronto, Canada: Biz from $534. Econ from $227. – Oct-Dec
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 $287. Econ from $88. – Oct-Dec (Including Thanksgiving)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Abu Dhabi, United Arab Emirates: Econ from $796. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Malaga, Spain: Econ from $436. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Boston, Massachusetts: Biz from $369. 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…