Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Ontario, California: Econ from $118. – Jan-Mar (Including President’s Day Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Atlanta, Georgia: Biz from $479 Econ from $61. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Abuja, Nigeria: Biz from $3317 Econ from $991. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > San Juan, Puerto Rico: Biz from $887 Econ from $126. – Jan-Mar
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 $64. – Jan-Mar
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Phoenix, Arizona: Econ from $76. – Jan-Mar
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Managua, Nicaragua: Biz from $1146 Econ from $187. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Baltimore, Maryland: Econ from $77. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Norfolk, Virginia: Biz from $505 Econ from $92. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Cartagena, Colombia: Biz from $923 Econ from $228. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Athens, Greece: Econ from $429. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Austin, Texas: Econ from $142. – Jan-Mar
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Marrakesh, Morocco: Econ from $606. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > San Salvador, El Salvador: Biz from $676 Econ from $232. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Atlantic City, New Jersey: Econ from $102. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > San Jose, Costa Rica: Biz from $1225 Econ from $233. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Guatemala City, Guatemala: Biz from $815 Econ from $187. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New Orleans, Louisiana: Biz from $408 Econ from $90. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Cape Town, South Africa: Econ from $942. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Bucharest, Romania: Econ from $527. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Christiansted, U.S. Virgin Islands: Econ from $184. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $387 Econ from $51. – Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Denver, Colorado: Econ from $58. – Jan-Mar
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $178. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dallas, Texas: Biz from $408 Econ from $70. – Jan-Mar (Including President’s Day Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Simpson Bay, St. Maarten: Econ from $243. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tunis, Tunisia: Biz from $2548 Econ from $770. – Jan-Mar (Including President’s Day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Christiansted, U.S. Virgin Islands: Econ from $184. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tirana, Albania: Biz from $2633 Econ from $569. – Jan-Mar (Including President’s Day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Luqa, Malta: Econ from $621. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Punta Cana, Dominican Republic: Biz from $824 Econ from $239. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Gdansk, Poland: Econ from $431. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Medellin, Colombia: Biz from $864 Econ from $253. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Santa Ana, California: Econ from $123. – Jan-Mar
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 $1036 Econ from $218. – Jan-Mar
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Cluj Napoca, Romania: Econ from $534. – Jan-Mar (Including President’s Day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Diego, California: Econ from $119. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Nashville, Tennessee: Biz from $420 Econ from $95. – Jan-Mar
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
MDW > Montego Bay, Jamaica: Biz from $1075 Econ from $255. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…