JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
MDW > Denver, Colorado: Biz from $502 Econ from $58. – Aug-Oct
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Knoxville, Tennessee: Econ from $83. – May-Jul (Including Summer Break)
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 $38. – Mar-May
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Cozumel, Mexico: Biz from $715 Econ from $315. – Sep-Nov (Including Fall Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Savannah, Georgia: Biz from $630 Econ from $75. – Apr-Jun (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Dublin, Ireland: Econ from $353. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cincinnati, Ohio: Biz from $264 Econ from $119. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Diego, California: Econ from $109. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Francisco, California: Econ from $104. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Houston, Texas: Econ from $68. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cancun, Mexico: Biz from $703 Econ from $183. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Raleigh, North Carolina: Biz from $444 Econ from $58. – Apr-Jun
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
ORD > Guadalajara, Mexico: Biz from $803 Econ from $273. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Washington, DC: Econ from $51. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > San Juan, Puerto Rico: Econ from $133. – Apr-Jun
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 $63. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Philadelphia, Pennsylvania: Econ from $48. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cali, Colombia: Biz from $939 Econ from $264. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $387 Econ from $60. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Montego Bay, Jamaica: Econ from $913. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Antonio, Texas: Econ from $99. – Apr-Jun
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 $61. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Phoenix, Arizona: Econ from $68. – Apr-Jun
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
MDW > Knoxville, Tennessee: Econ from $79. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Pedro Sula, Honduras: Biz from $900. Econ from $198. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Denver, Colorado: Econ from $48. – Mar-May
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1153. Econ from $566. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Atlanta, Georgia: Biz from $409. Econ from $39. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Minneapolis, Minnesota: Biz from $284 Econ from $77. – Mar-May
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Norfolk, Virginia: Econ from $107. – Mar-May
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
(Including Labor Day) ORD > Cozumel, Mexico: Biz from $635 Econ from $262. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
MDW > Guatemala City, Guatemala: Econ from $158. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Punta Cana, Dominican Republic: Biz from $923 Econ from $233. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Oranjestad, Aruba: Econ from $263. – Apr-Jun
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
MDW > Boston, Massachusetts: Biz from $459 Econ from $101. – Apr-Jun
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
MDW > Raleigh, North Carolina: Econ from $50. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > San Jose, Costa Rica: Biz from $1276 Econ from $198. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Salt Lake City, Utah: Econ from $95. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Houston, Texas: Econ from $68. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…