Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Lisbon, Portugal: Econ from $461. – Oct-Dec (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > New Delhi, India: Econ from $615. – 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…
ORD > Hartford, Connecticut: Biz from $563 Econ from $158. – 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 > Piarco, Trinidad and Tobago: Biz from $860 Econ from $308. – 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 > Mumbai, India: Econ from $614.- Aug-Oct (Including Labor Day)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Knoxville, Tennessee: Econ from $98.- May-Jul (Including Summer Break)
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: Biz from $184. Econ from $58. – Apr-Jun
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Austin, Texas: Biz from $357 Econ from $105.- Feb-Apr (Including Spring Break)
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Athens, Greece: Econ from $510. – 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…
MDW > Asheville, North Carolina: Econ from $97. – 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 > Denver, Colorado: Biz from $381 Econ from $82. – Feb-Apr (Including Spring Break)
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > Memphis, Tennessee: Biz from $266 Econ from $97. – Feb-Apr (Including Spring Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Columbus, Ohio: Biz from $267 Econ from $97. – Feb-Apr (Including Spring Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Auckland, New Zealand: Econ from $681. – Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Jose, Costa Rica: Econ from $325.- Feb-Apr (Including Spring Break)
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 $174 Econ from $56.- Feb-Apr (Including Spring Break)
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Pristina, Kosovo: Econ from $528.- Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Oranjestad, Aruba: Biz from $519 Econ from $231.- Feb-Apr (Including Spring Break)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > San Salvador, El Salvador: Biz from $508 Econ from $227.- Feb-Apr (Including Spring Break)
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 $261 Econ from $107.- Feb-Apr (Including Spring Break)
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Phoenix, Arizona: Econ from $83.- Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Charlotte, North Carolina: Biz from $281 Econ from $94.- Feb-Apr (Including Spring Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Casablanca, Morocco: Econ from $561. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cartagena, Colombia: Biz from $577 Econ from $237. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Raleigh, North Carolina: Biz from $406 Econ from $110.- Feb-Apr
3 different flights to/from Raleigh – All under $100 round-trip. * There only appear to be a few seats at…
MDW > Brasilia, Brazil: Econ from $684.- Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cincinnati, Ohio: Biz from $352 Econ from $150. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Willemstad, Curaçao: Biz from $1086 Econ from $377. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Miami, Florida: Biz from $212 Econ from $50.- Feb-Apr (Including Spring Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Punta Cana, Dominican Republic: Biz from $682 Econ from $191.- Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Los Angeles, California: Biz from $344 Econ from $88.- Feb-Apr (Including Spring Break)
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Cuenca, Ecuador: Biz from $1007 Econ from $440.- Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Boston, Massachusetts: Biz from $286 Econ from $104.- Feb-Apr (Including Spring Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Gdansk, Poland: Econ from $439.- Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Philadelphia, Pennsylvania: Biz from $354 Econ from $112. – Jan-Mar (Presidents day Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Palanga, Lithuania: Econ from $472. – Feb-Apr (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cancun, Mexico: Biz from $494 Econ from $239. – Feb-Apr (Including Spring Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Atlanta, Georgia: Biz from $557 Econ from $58.- Jan-Mar (Presidents day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Tunis, Tunisia: Econ from $856.- Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…