For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Savannah, Georgia: Econ from $46. Biz from $446 (Business Bargain). – Oct-Dec [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Atlanta, Georgia: Econ from $39. Biz from $355 (Business Bargain). – Oct-Dec [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 > New Orleans, Louisiana: Econ from $69. Biz from $335 (Business Bargain). – Oct-Dec [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Fort Lauderdale, Florida: Econ from $61. Biz from $415 (Business Bargain). – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cleveland, Ohio: Econ from $71. Biz from $274 (Business Bargain). – Oct-Dec [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Oranjestad, Aruba: From $228 round-trip – Oct-Dec *BB [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Boston, Massachusetts: From $42 round-trip – Oct-Dec *BB [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Atlanta, Georgia: From $48 round-trip – Oct-Dec *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Houston, Texas: From $72 round-trip – Oct-Dec [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 > San Diego, California: From $48 round-trip – Oct-Dec *BB [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: From $90 round-trip – Sep-Nov *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Minneapolis, Minnesota: From $65 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Santo Domingo, Dominican Republic: From $219 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Skopje, North Macedonia: From $351 round-trip – Oct-Dec [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 > Myrtle Beach, South Carolina: From $70 round-trip – 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 > New York, New York: From $65 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Newark, New Jersey: From $64 round-trip – Oct-Dec *BB [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Washington, DC: From $49 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Miami, Florida: From $47 round-trip – Oct-Dec [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Raleigh, North Carolina: From $67 round-trip – Sep-Nov *BB [SOLD OUT]
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
ORD > Barranquilla, Colombia: From $161 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Columbus, Ohio: From $71 round-trip – Oct-Dec *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Knoxville, Tennessee: From $70 round-trip – Sep-Nov (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…
MDW > Anchorage, Alaska: From $286 round-trip – Sep-Nov [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Guayaquil, Ecuador: From $221 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Atlanta, Georgia: From $51 round-trip – Sep-Nov *BB [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: From $26 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Bogota, Colombia: From $159 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Lima, Peru: From $260 round-trip – Sep-Nov (Including Fall Break) *BB [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 > Tampa, Florida: From $49 round-trip – 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 > Houston, Texas: From $35 round-trip – 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 Jose, Costa Rica: From $202 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Baltimore, Maryland: From $50 round-trip – Sep-Nov (Including Fall Break) *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New Orleans, Louisiana: From $37 round-trip – 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 > San Juan, Puerto Rico: From $86 round-trip – Sep-Nov *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Istanbul, Turkey: From $487 round-trip – Oct-Dec [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 > Simpson Bay, Sint Maarten: From $202 round-trip – 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 > Nashville, Tennessee: From $62 round-trip – Sep-Nov *BB [SOLD OUT]
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > Denver, Colorado: From $45 round-trip – Sep-Nov *BB [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…