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: Econ from $114. – May-Jul (Including Summer Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Valparaiso, Florida: Econ from $64. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > San Juan, Puerto Rico: Biz from $581 Econ from $215. – May-Jul (Including Summer Break) [SOLD OUT]
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 $368 Econ from $79. – May-Jul (Including Summer Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Savannah, Georgia: Biz from $535 Econ from $79. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Medellin, Colombia: Biz from $869 Econ from $292. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fairbanks, Alaska: Biz from $887 Econ from $277. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Decatur, Georgia: Econ from $115. – May-Jul (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Newark, New Jersey: Biz from $339 Econ from $76. – May-Jul (Including Summer 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 > San Jose, Costa Rica: Biz from $967 Econ from $240. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Stockholm, Sweden: Econ from $314. – Jun-Aug (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Fort Lauderdale, Florida: Biz from $435 Econ from $56. – May-Jul (Including Summer 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 > Orlando, Florida: Biz from $435 Econ from $63. – May-Jul (Including Summer Break) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * There only…
ORD > Cartagena, Colombia: Biz from $793 Econ from $245. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Philadelphia, Pennsylvania: Biz from $401 Econ from $122. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Guayaquil, Ecuador: Biz from $1,025 Econ from $217. – May-Jul (Including Summer Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Fort Myers, Florida: Biz from $435 Econ from $38. – May-Jul (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Guatemala City, Guatemala: Biz from $606 Econ from $177. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Moscow, Russia: Econ from $448. – Jul-Sep (Including Summer Break) [SOLDOUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Burlington, Kentucky: Econ from $68. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Knoxville, Tennessee: Econ from $70. – Apr-Jun (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Juneau, Alaska: Biz from $1,031 Econ from $334. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Minneapolis, Minnesota: Biz from $277 Econ from $99. – Apr-Jun (Including Summer Break) [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Boston, Massachusetts: Biz from $317 Econ from $97. – May-Jul (Including Summer Break) [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Myrtle Beach, South Carolina: Biz from $410 Econ from $78. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Merida, Mexico: Biz from $713 Econ from $222. – May-Jul (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Ketchikan, Alaska: Biz from $887 Econ from $240. – May-Jul (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Oakland, California: Econ from $143. – May-Jul (Including Summer 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 > Istanbul, Turkey: Econ from $526. – May-Jul (Including Summer Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Bucaramanga, Colombia: Biz from $910 Econ from $325. – Jun-Aug (Including Summer Break) [SOLD OUT]
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 $336. – Jun-Aug (Including Fourth of July) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cusco, Peru: Econ from $456. – Jun-Aug (Including Fourth of July) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Copenhagen, Denmark: Econ from $348. – Jul-Sep (Including Summer Break) [SOLDOUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Valparaiso, Florida: Econ from $92. – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Rio de Janeiro, Brazil: Biz from $2222 Econ from $639. – Jul-Sep (Including Summer Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dubai, United Arab Emirates: Econ from $552. – Jun-Aug (Including Fourth of July) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Dubrovnik, Croatia: Biz from $1,770 Econ from $600. – Jun-Aug (Including Fourth of July) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
MDW > Savannah, Georgia: Biz from $502 Econ from $76. – Apr-Jun (Including Summer 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 > Guayaquil, Ecuador: Biz from $832 Econ from $315. – May-Jul (Including Summer Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…