3 different flights to/from Raleigh – All under $100 round-trip. * This is an airline sale that is time-sensitive. Plenty…
ORD > Managua, Nicaragua: Biz from $912 Econ from $325. – Oct-Dec
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 $915. – Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Dublin, Ireland: Econ from $343. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Econ from $613. – Mar-May
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > Jacksonville, Florida: Biz from $627 Econ from $114. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Guatemala City, Guatemala: Econ from $222. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New York, New York: Biz from $379 Econ from $74. – Sep-Nov (Including Fall Break)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Denver, Colorado: Biz from $399 Econ from $57. – Sep-Nov (Including Fall Break)
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
MDW > Wroclaw, Poland: Econ from $458. – 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 > Tallinn, Estonia: Econ from $463. – Oct-Dec (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $958 Econ from $229. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Barcelona, Spain: Econ from $341. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Abuja, Nigeria: Econ from $836. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Diego, California: Econ from $94. – Sep-Nov
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Dallas, Texas: Biz from $429 Econ from $67. – Sep-Nov (Including Fall Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Jose, Costa Rica: Biz from $1163 Econ from $227. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sofia, Bulgaria: Econ from $466. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Burbank, California: Econ from $84. – Sep-Nov (Including Fall Break)
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 $693. – Dec-Feb (Including MLK Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Montego Bay, Jamaica: Biz from $953 Econ from $342. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Innsbruck, Austria: Econ from $511. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Tunis, Tunisia: Biz from $2641 Econ from $773. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Myrtle Beach, South Carolina: Biz from $416 Econ from $42. – Sep-Nov
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Pedro Sula, Honduras: Biz from $878 Econ from $292. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Econ from $311. – Oct-Dec
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
MDW > Salt Lake City, Utah: Econ from $108. – Sep-Nov
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Krakow, Poland: Econ from $455. – Jan-Mar (Including President’s Day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Knoxville, Tennessee: Biz from $418 Econ from $81. – Oct-Dec
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Sarajevo, Bosnia and Herzegovina: Econ from $485. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Mykonos, Greece: Econ from $598. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Zagreb, Croatia: Econ from $499. – Jan-Mar
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
MDW > New Orleans, Louisiana: Econ from $71. – Oct-Dec
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Fort Lauderdale, Florida: Econ from $50. – Sep-Nov
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Juan, Puerto Rico: Econ from $124. – Oct-Dec (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cozumel, Mexico: Biz from $974. Econ from $310. – Jan-Mar
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Phoenix, Arizona: Econ from $72. – Sep-Nov (Including Fall Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Portland, Oregon: Econ from $35. – Sep-Nov (Including Fall Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Thera, Greece: Econ from $571. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Skopje, North Macedonia: Econ from $452. – Oct-Dec (Including Fall Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…