Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Oslo, Norway: Econ from $380. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Salt Lake City, Utah: Biz from $524 Econ from $73. – Aug-Oct
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Philadelphia, Pennsylvania: Biz from $414 Econ from $37. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Pristina, Kosovo: Econ from $520. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $994 Econ from $215. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dublin, Ireland: Econ from $325. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Riga, Latvia: Econ from $395. – 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 > Hartford, Connecticut: Biz from $391 Econ from $121. – 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 > Denver, Colorado: Biz from $526 Econ from $42. – Aug-Oct
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Guatemala City, Guatemala: Econ from $173. – Jan-Mar
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 $353. – Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Missoula, Montana: Econ from $110. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Savannah, Georgia: Biz from $477 Econ from $146. – Aug-Oct
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Dubai, United Arab Emirates: Econ from $609. – Oct-Dec (Including Thanksgiving)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Jose, Costa Rica: Biz from $1118 Econ from $211. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sarajevo, Bosnia and Herzegovina: Econ from $491. – Nov-Jan (Including Winter Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Podgorica, Montenegro: Biz from $2613 Econ from $727. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Jacksonville, Florida: Biz from $521 Econ from $120. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Pedro Sula, Honduras: Biz from $856 Econ from $230. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Burbank, California: Econ from $96. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Larnaca, Cyprus: Econ from $612. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dallas, Texas: Biz from $506. Econ from $35. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Budapest, Hungary: Econ from $483. – Jan-Mar (Including President’s Day Weekend)
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 $877. Econ from $249. – 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 > Houston, Texas: Biz from $527. Econ from $55. – Aug-Oct
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Porto, Portugal: Econ from $433. – Oct-Dec
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 $66. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Johannesburg, South Africa: Econ from $786. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > San Juan, Puerto Rico: Biz from $743. Econ from $132. – Sep-Nov
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 $71. – Aug-Oct
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Santiago de Queretaro, Mexico: Biz from $811. Econ from $262. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Krakow, Poland: Econ from $531. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Sacramento, California: Econ from $84. – Aug-Oct
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Tunis, Tunisia: Econ from $779. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Portland, Oregon: Econ from $88. – Aug-Oct (Including Labor Day)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Phoenix, Arizona: Econ from $70. – Aug-Oct
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Puerto Escondido, Mexico: Econ from $247. – Jan-Mar
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 $613. – Sep-Nov (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Belgrade, Serbia: Biz from $2028. Econ from $514. – 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…