Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Kingston, Jamaica: Biz from $909 Econ from $278. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sacramento, California: Biz from $895 Econ from $134. – Sep-Nov [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Dallas, Texas: Biz from $537 Econ from $39. – Sep-Nov [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 > Cartagena, Colombia: Biz from $921 Econ from $226. – Oct-Dec [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Panama City, Panama: Biz from $1103 Econ from $406. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Baltimore, Maryland: Biz from $413 Econ from $67. – Oct-Dec (Including Fall 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 > Los Angeles, California: Econ from $69. – Sep-Nov [SOLD OUT]
Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…
ORD > Montego Bay, Jamaica: Biz from $939 Econ from $254. – Sep-Nov (Including Fall 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 > Vilnius, Lithuania: Econ from $399. – Sep-Nov (Including Fall 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…
MDW > Hartford, Connecticut: Biz from $589 Econ from $134. – Sep-Nov [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fort Lauderdale, Florida: Econ from $45. – Sep-Nov (Including Fall Break) [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
MDW > Philadelphia, Pennsylvania: Biz from $412 Econ from $40. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Orlando, Florida: Econ from $40. – Sep-Nov (Including Fall Break) [SOLD OUT]
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Oranjestad, Aruba: Econ from $238. – Sep-Nov [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > New York, New York: Biz from $433 Econ from $92. – Sep-Nov [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Split, Croatia: Econ from $611. – Sep-Nov (Including Fall Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Prague, Czech Republic: Econ from $416. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Christiansted, U.S. Virgin Islands: Biz from $1183 Econ from $250. – Sep-Nov [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 Salvador, El Salvador: Biz from $1043 Econ from $194. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boise, Idaho: Biz from $468 Econ from $128. – Sep-Nov (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Phoenix, Arizona: Econ from $80. – Sep-Nov (Including Fall Break) [SOLD OUT]
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $217. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Ontario, California: Econ from $115. – Sep-Nov (Including Fall 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 > Austin, Texas: Biz from $536 Econ from $114. – Sep-Nov [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Sofia, Bulgaria: Econ from $545. – Oct-Dec (Including Fall Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Barranquilla, Colombia: Biz from $867 Econ from $298. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cluj Napoca, Romania: Econ from $540. – Oct-Dec (Including Fall Break) [SOLD OUT]
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
MDW > San Francisco, California: Econ from $100. – Sep-Nov (Including Fall Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Burbank, California: Econ from $114. – Sep-Nov [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 > Port Au Prince, Haiti: Econ from $246. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Mykonos, Greece: Econ from $638. – Sep-Nov (Including Fall 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 > San Jose, California: Econ from $110. – Sep-Nov [SOLD OUT]
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Atlantic City, New Jersey: Biz from $478 Econ from $74. – Sep-Nov [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 Pedro Sula, Honduras: Biz from $733 Econ from $259. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kuwait City, Kuwait: Econ from $763. – Sep-Nov [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 > Houston, Texas: Econ from $89. – Sep-Nov [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 > Alicante, Spain: Econ from $382. – Sep-Nov (Including Fall 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 > Cali, Colombia: Biz from $1006 Econ from $256. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Guatemala City, Guatemala: Biz from $777 Econ from $218. – Aug-Oct [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…