Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Ontario, California: Econ from $88. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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 > Prague, Czech Republic: Econ from $457. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cape Town, South Africa: Econ from $836. – 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 > 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…
ORD > Larnaca, Cyprus: Econ from $592.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Riga, Latvia: Econ from $440.- 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 > San Pedro Sula, Honduras: Biz from $725 Econ from $293.- Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Poznan, Poland: Econ from $443. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Econ from $550. – Apr-Jun
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
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 > Cluj Napoca, Romania: Econ from $509.- Mar-May
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Punta Cana, Dominican Republic: Biz from $827 Econ from $219.- Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cuenca, Ecuador: Biz from $1003 Econ from $461.- Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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…
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 > Algiers, Algeria: Econ from $558. – 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 > 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…
ORD > Madrid, Spain: Econ from $387. – Oct-Dec
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Marrakesh, Morocco: Econ from $566. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Honolulu, Hawaii: Econ from $341. – Mar-May
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Guadalajara, Mexico: Biz from $614 Econ from $252. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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…
ORD > Mykonos, Greece: Econ from $657.- Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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.…
MDW > Tunis, Tunisia: Econ from $782.- Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Los Angeles, California: Biz from $377 Econ from $88.- Apr-Jun
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Barcelona, Spain: Econ from $367.- Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
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 > Philadelphia, Pennsylvania: Biz from $366 Econ from $97. – Mar-May
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Nadi, Fiji: Econ from $771. – Aug-Oct
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > George Town, Cayman Islands: Biz from $1051 Econ from $346. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sibiu, Romania: Econ from $555. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Tokyo, Japan: Econ from $624. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Georgetown, Guyana: Biz from $768 Econ from $396. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dublin, Ireland: Econ from $414. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…