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 > 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 > 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 > 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…
ORD > Oranjestad, Aruba: Biz from $968. Econ from $346. – Nov-Jan
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Palanga, Lithuania: Econ from $428. – 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 > Barcelona, Spain: Econ from $360. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Miami, Florida: Econ from $93. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Pedro Sula, Honduras: Biz from $1259. Econ from $267. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cancun, Mexico: Biz from $431 Econ from $238. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Punta Cana, Dominican Republic: Biz from $770 Econ from $205. – Dec-Feb (Including MLK Weekend)
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 $1068. – 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 > Fort Lauderdale, Florida: Biz from $343. Econ from $92. – Sep-Nov [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Willemstad, Curaçao: Biz from $1074. Econ from $350. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Luqa, Malta: Econ from $464. – 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 Salvador, El Salvador: Biz from $759. Econ from $214. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Bali, Indonesia: Econ from $687. – 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 > Lisbon, Portugal: Econ from $461. – Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Liberia, Costa Rica: Biz from $1257 Econ from $309. – Sep-Nov (Including Fall Break) [SOLD OUT]
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Palma de Mallorca, Spain: Econ from $422. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…