Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Anchorage, Alaska: Econ from $339. -April-June
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Fortaleza, Brazil: Econ from $857. – Sep-Nov (Including Fall Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
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…
MDW > Christiansted, U.S. Virgin Islands: Econ from $342. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Heraklion, Greece: Econ from $702. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: Econ from $566. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Charleston, South Carolina: Econ from $93. – 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 > Baltimore, Maryland: Econ from $58. – 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 > 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 > Kansas City, Kansas: Biz from $395 Econ from $137. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Krakow, Poland: Econ from $533. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Johannesburg, South Africa: Econ from $757. – Oct-Dec
* This is a “fare dump” with a few alternate dates available.
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 > Warsaw, Poland: Econ from $511. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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 > Charlotte, North Carolina: Biz from $407 Econ from $55. – 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 > 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.…
MDW > Dubai, United Arab Emirates: Econ from $1046. – Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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.…
ORD > Dubai, United Arab Emirates: Econ from $675. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Boise, Idaho: Econ from $154. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Georgetown, Guyana: Biz from $1,060 Econ from $441. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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 > Dublin, Ireland: Econ from $425. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Denver, Colorado: Biz from $499 Econ from $58. – Apr-Jun
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
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 > Cape Town, South Africa: Econ from $940. – Oct-Dec (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Prague, Czech Republic: Econ from $541. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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…
MDW > Philadelphia, Pennsylvania: Biz from $430 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 > 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.…