Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Jacksonville, Florida: Biz from $509. Econ from $162. – Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Prague, Czech Republic: Econ from $408. – Jan-Mar (Presidents day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Coxen Hole, Honduras: Biz from $952. Econ from $472. – Dec-Feb (Including MLK Weekend)
A lot of people are concerned about travel to Honduras, but Coxen Hole (AKA “Roatan”) is an island off of…
ORD > Fort Lauderdale, Florida: Biz from $333 Econ from $56. – 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…
ORD > Dubai, United Arab Emirates: Econ from $589. – Dec-Feb (Including MLK Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Wroclaw, Poland: Econ from $385. – 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…
ORD > Minneapolis, Minnesota: Biz from $376 Econ from $88. – Dec-Feb (Including Winter Break)
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Austin, Texas: Biz from $290 Econ from $80. – Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Nadi, Fiji: Econ from $1074. – Dec-Feb (Including MLK Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Colombo, Sri Lanka: Econ from $748. – 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 > Los Angeles, California: Biz from $367. Econ from $135. – Nov-Jan (Including Winter Break)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Amman, Jordan: Econ from $730.- 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 > Iaşi, Romania: Econ from $548. – 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 > Reno, Nevada: Econ from $161. – Dec-Feb (Including Winter Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Cincinnati, Ohio: Biz from $401. Econ from $137. – Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Osaka, Japan: Econ from $760. – Dec-Feb (Including MLK Weekend)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Corfu, Greece: Econ from $692. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > San Salvador, El Salvador: Econ from $286. – Dec-Feb (Including MLK Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Phoenix, Arizona: Econ from $73. – Jan-Mar (Presidents day Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Las Vegas, Nevada: Econ from $58. – Dec-Feb (Including MLK Weekend)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Liberia, Costa Rica: Biz from $1038. Econ from $371. – Feb-Apr (Including Spring Break)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Bucharest, Romania: Econ from $523. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Colombo, Sri Lanka: Econ from $735. – Mar-May (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > San Diego, California: Econ from $155. – Nov-Jan (Including Thanksgiving)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Prague, Czech Republic: Econ from $447. – 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 > Pittsburgh, Pennsylvania: Biz from $287. Econ from $134. – Dec-Feb (Including MLK Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Kinshasa, Democratic Republic of the Congo: Econ from $916. – Dec-Feb (Including MLK Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Fort Myers, Florida: Biz from $330. Econ from $73. – Dec-Feb (Including MLK Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Dubai, United Arab Emirates: Econ from $589. – 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 > New Orleans, Louisiana: Biz from $303 Econ from $96. – Dec-Feb (Including MLK Weekend)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Phoenix, Arizona: Econ from $79. – Dec-Feb (Including MLK Weekend)
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Belgrade, Serbia: Econ from $485. – 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 > Palma de Mallorca, Spain: Econ from $414. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Berlin, Germany: Econ from $434. – 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…
ORD > Cairo, Egypt: Econ from $588. – 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 > Raleigh, North Carolina: Econ from $83. – Oct-Dec (Including Thanksgiving)
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
MDW > Knoxville, Tennessee: Econ from $111. – Oct-Dec (Including Thanksgiving)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Colombo, Sri Lanka: Econ from $774. – Mar-May (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 > Cluj Napoca, Romania: Econ from $518. – Feb-Apr (Including Spring Break)
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…