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…
MDW > San Juan, Puerto Rico: Econ from $189. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Burbank, California: Econ from $90. – 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 > Fort Myers, Florida: Biz from $331 Econ from $69. – Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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 > Boston, Massachusetts: Biz from $369 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 > 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 > 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 > 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 > Baltimore, Maryland: Biz from $309 Econ from $66. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
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 > Orlando, Florida: Biz from $247 Econ from $82. – Feb-Apr
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cancun, Mexico: Biz from $721 Econ from $200. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New Orleans, Louisiana: Biz from $215. Econ from $68. – Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Houston, Texas: Biz from $286. Econ from $56. – 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 > 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…
ORD > Palanga, Lithuania: Econ from $451. – 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 > Managua, Nicaragua: Biz from $506. Econ from $250. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Budapest, Hungary: Econ from $459.- Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dallas, Texas: Biz from $277 Econ from $55.- Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Bucharest, Romania: Econ from $497.- Jul-Sep
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
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 > Atlanta, Georgia: Biz from $278 Econ from $56.- Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Addis Ababa, Ethiopia: Econ from $943.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Krakow, Poland: Econ from $432. – Oct-Dec
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…