* 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,…
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 > 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 > 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.…
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 > 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 > 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 > 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 > 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 > 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…
ORD > Stockholm, Sweden: Econ from $315. – 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 > Copenhagen, Denmark: Econ from $311. – 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 > Arequipa, Peru: Biz from $1,571 Econ from $481. – 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 > Juneau, Alaska: Biz from $922 Econ from $362. – Jun-Aug (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…
MDW > Clarksburg, West Virginia: Econ from $62. – 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 > Faro, Portugal: Biz from $1,341 Econ from $377. – Jun-Aug (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 > Reykjavik, Iceland: Econ from $396. – 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 > Reykjavik, Iceland: Econ from $379. – 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 > Ketchikan, Alaska: Biz from $846 Econ from $410. – Jun-Aug (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 > Arequipa, Peru: Econ from $482. – 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 > Accra, Ghana: Biz from $1,911 Econ from $382. – Jun-Aug (Including Fourth of July) [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 > Arequipa, Peru: Econ from $477. – Jun-Aug (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…
MDW > Toronto, Canada: Econ from $264. – Jul-Sep (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 > Dubrovnik, Croatia: From $473 round-trip – Jun-Aug (Including Fourth of July) *BB [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…