Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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 > 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…
ORD > Male, Maldives: Econ from $950. – Jan-Mar (Presidents day Weekend)
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 $411. – Nov-Jan (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Boston, Massachusetts: Biz from $351 Econ from $117. – Jan-Mar
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 $957 Econ from $311. – Dec-Feb
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Barcelona, Spain: Econ from $372. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Rabat, Morocco: Econ from $529. – Nov-Jan (Including Thanksgiving)
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)
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 $128. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Funchal, Portugal: Econ from $470. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kingston, Jamaica: Biz from $925. Econ from $352. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Cancun, Mexico: Biz from $438 Econ from $202. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Punta Cana, Dominican Republic: Econ from $201. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Phu Quoc, Vietnam: Econ from $992. – Feb-Apr (Including Spring Break)
Do you like Vietnamese Pho? Here is a recipe my childhood friend Hien taught me. * This is an airline…
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 > Luqa, Malta: Econ from $397. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Palma de Mallorca, Spain: Econ from $402. – 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 > 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 > 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 > Liberia, Costa Rica: Biz from $952. Econ from $307. – Dec-Feb
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Belize City, Belize: Biz from $696. Econ from $376. – Nov-Jan
* This is a “fare dump” with a few alternate dates available.
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…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1168 Econ from $573. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Florianopolis, Brazil: Biz from $2102 Econ from $808. – Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Tampa, Florida: Biz from $368 Econ from $119. – Sep-Nov (Including Fall 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 > George Town, Cayman Islands: Biz from $619 Econ from $320. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 –…
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 > Los Angeles, California: Biz from $539 Econ from $131. – Sep-Nov (Including Fall 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 > 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 > 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…
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…