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.…
ORD > New Orleans, Louisiana: Biz from $409 Econ from $59. – 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 > Phoenix, Arizona: Econ from $75. – Mar-May
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
MDW > Krakow, Poland: Econ from $531. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Bogota, Colombia: Biz from $835 Econ from $225. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1498 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.…
ORD > Athens, Greece: Econ from $512. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Kansas City, Kansas: Biz from $288 Econ from $108. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Atlanta, Georgia: Biz from $479 Econ from $38. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Porto, Portugal: Econ from $500. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > New York, New York: Econ from $53. – Mar-May
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Minneapolis, Minnesota: Biz from $288 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…
ORD > Budapest, Hungary: Econ from $511. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Pedro Sula, Honduras: Biz from $792 Econ from $200. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Atlantic City, New Jersey: Econ from $108. – 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 > Heraklion, Greece: Econ from $668. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Montego Bay, Jamaica: Biz from $911 Econ from $234. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Georgetown, Guyana: Biz from $910 Econ from $397. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Los Angeles, California: Econ from $120. – Mar-May
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Nadi, Fiji: Econ from $1166. – Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cali, Colombia: Biz from $853 Econ from $256. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Santa Ana, California: Econ from $120. – Apr-Jun
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Asheville, North Carolina: Econ from $78. – 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 > Guatemala City, Guatemala: Econ from $191. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Diego, California: Econ from $120. – Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Panama City, Panama: Biz from $1040 Econ from $367. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Denver, Colorado: Biz from $499 Econ from $37. – Mar-May
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Kingston, Jamaica: Biz from $738 Econ from $310. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boise, Idaho: Econ from $156. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Charlotte, North Carolina: Biz from $359 Econ from $45. – Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cozumel, Mexico: Biz from $645 Econ from $172. – Apr-Jun
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Reno, Nevada: Econ from $156. – Mar-May
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
ORD > Prague, Czech Republic: Econ from $531. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Ontario, California: Econ from $113. – 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 > Larnaca, Cyprus: Econ from $687. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Savannah, Georgia: Econ from $78. – Mar-May
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Abuja, Nigeria: Biz from $3503 Econ from $979. – Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Punta Cana, Dominican Republic: Biz from $755 Econ from $179. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Boston, Massachusetts: Econ from $80. – Mar-May
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…