Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Malaga, Spain: Econ from $411. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Philadelphia, Pennsylvania: Biz from $322 Econ from $106. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Rabat, Morocco: Econ from $529. – Nov-Jan (Including Thanksgiving) [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 > Simpson Bay, St. Maarten: Econ from $375. – Oct-Dec (Including Thanksgiving) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charleston, South Carolina: Econ from $108. – Oct-Dec [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 Francisco, California: Econ from $128. – 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 > Miami, Florida: Biz from $206. Econ from $68. – 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 > Houston, Texas: Econ from $78. – Oct-Dec [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 > Algiers, Algeria: Econ from $539. – Nov-Jan (Including Thanksgiving) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cincinnati, Ohio: Biz from $365 Econ from $108. – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Dallas, Texas: Econ from $64. – Oct-Dec [SOLD OUT]
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 [SOLD OUT]
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) [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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) [SOLD OUT]
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 [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 > Willemstad, Curaçao: Biz from $1399 Econ from $454. – Nov-Jan [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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) [SOLD OUT]
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 [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 Diego, California: Econ from $153. – 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…
ORD > Okinawa, Japan: Econ from $961. – Oct-Dec [SOLD OUT]
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) [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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) [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 > Denver, Colorado: Biz from $423 Econ from $74. – Oct-Dec [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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 [SOLD OUT]
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…