Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Valparaiso, Florida: Econ from $66. – 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…
ORD > Houston, Texas: Biz from $565 Econ from $88. – Jul-Sep (Including Summer Break) [SOLDOUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Rio de Janeiro, Brazil: Biz from $1,816 Econ from $537. – Jul-Sep (Including Summer Break) [SOLDOUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Budapest, Hungary: Biz from $1,786 Econ from $548. – 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 > Las Vegas, Nevada: Econ from $69. – Jul-Sep (Including Summer Break) [SOLDOUT]
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…
ORD > Decatur, Georgia: Econ from $115. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Knoxville, Tennessee: Econ from $88. – Jul-Sep (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…
ORD > Rome, Italy: Econ from $358. – Jun-Aug (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…
MDW > Toronto, Canada: Econ from $328. – Jul-Sep (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 > Dubrovnik, Croatia: Econ from $582. – Jun-Aug (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Panama City, Panama: Biz from $683 Econ from $265. – Jul-Sep (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…
MDW > Valparaiso, Florida: Econ from $59. – Jun-Aug (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 > Reykjavik, Iceland: Econ from $449. – 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…
ORD > Mexico City, Mexico: Econ from $194. – Jul-Sep (Including Summer Break) [SOLDOUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Baltimore, Maryland: Econ from $96. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Savannah, Georgia: Biz from $535 Econ from $61. – Jun-Aug (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 > Oakland, California: Econ from $133. – Jun-Aug (Including Summer 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…
ORD > Greensboro, North Carolina: Econ from $166. – 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 > Santa Maria Huatulco, Mexico: Econ from $237. – 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 > New Orleans, Louisiana: Econ from $81. – Jun-Aug (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…
ORD > Guayaquil, Ecuador: Biz from $867 Econ from $380. – 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 > Fairbanks, Alaska: Biz from $952 Econ from $277. – 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 > Oaxaca, Mexico: Econ from $240. – 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 > San Pedro Sula, Honduras: Biz from $614 Econ from $296. – Jul-Sep (Including Summer Break) [SOLDOUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Austin, Texas: Biz from $533 Econ from $69. – Jul-Sep (Including Summer Break) [SOLDOUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
MDW > Savannah, Georgia: Biz from $534 Econ from $97. – Jun-Aug (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 > Cozumel, Mexico: Biz from $748 Econ from $287. – Jun-Aug (Including Summer Break) [SOLD OUT]
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Knoxville, Tennessee: Econ from $86. – 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 > Philadelphia, Pennsylvania: Econ from $157. – Jul-Sep (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 > Oakland, California: Econ from $123. – Jul-Sep (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 > Merida, Mexico: Biz from $692 Econ from $244. – Jul-Sep (Including Summer Break) [SOLDOUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Guayaquil, Ecuador: Biz from $851 Econ from $323. – Jun-Aug (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 > Casablanca, Morocco: Biz from $1,618 Econ from $575. – Jun-Aug (Including Summer Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Sitka, Alaska: Biz from $953 Econ from $340. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Burlington, Kentucky: Econ from $68. – Jun-Aug (Including Fourth of July) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Lisbon, Portugal: Econ from $335. – Jun-Aug (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 > Boston, Massachusetts: Biz from $369 Econ from $78. – Jun-Aug (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 > Baltimore, Maryland: Econ from $97. – 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…
ORD > Austin, Texas: Econ from $134. – May-Jul (Including Summer Break) [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…