Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
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…
MDW > Omaha, Nebraska: Biz from $425 Econ from $96. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Diego, California: Econ from $86. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Seattle, Washington: Biz from $499 Econ from $117. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Managua, Nicaragua: Biz from $931 Econ from $241. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Biz from $469 Econ from $117. – Mar-May
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 $977 Econ from $266. – 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 $68. – Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Ontario, California: Econ from $124. – Mar-May
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Montego Bay, Jamaica: Biz from $911 Econ from $238. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Phoenix, Arizona: Econ from $87. – Mar-May
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
MDW > San Pedro Sula, Honduras: Biz from $712 Econ from $256. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Francisco, California: Econ from $98. – Mar-May
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Punta Arenas, Chile: Econ from $802. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Salvador, El Salvador: Biz from $706 Econ from $184. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New York, New York: Biz from $379 Econ from $54. – Mar-May
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Athens, Greece: Econ from $596. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Atlanta, Georgia: Biz from $18 Econ from $48. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1181 Econ from $588. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Asheville, North Carolina: Econ from $78. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Santo Domingo, Dominican Republic: Biz from $889 Econ from $231. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Diego, California: Econ from $127. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Piarco, Trinidad and Tobago: Econ from $401. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Minneapolis, Minnesota: Biz from $308 Econ from $77. – Mar-May
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
MDW > Tirana, Albania: Econ from $719. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Kingston, Jamaica: Biz from $718 Econ from $318. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Larnaca, Cyprus: Econ from $629. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Boston, Massachusetts: Biz from $437 Econ from $116. – Mar-May
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Seattle, Washington: Biz from $499 Econ from $117. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Cairo, Egypt: Econ from $859. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Raleigh, North Carolina: Biz from $389 Econ from $85. – Mar-May
3 different flights to/from Raleigh – All under $100 round-trip. * This is an airline sale that is time-sensitive. Plenty…
ORD > Oranjestad, Aruba: Biz from $1003 Econ from $261. – Mar-May
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Thera, Greece: Econ from $507. – Mar-May
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Myrtle Beach, South Carolina: Econ from $110. – Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Skopje, North Macedonia: Econ from $521. – Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > San Francisco, California: Econ from $98. – Mar-May
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Sacramento, California: Econ from $130. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > San Salvador, El Salvador: Biz from $724 Econ from $237. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…