Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Diego, California: Econ from $119. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Nashville, Tennessee: Biz from $420 Econ from $95. – Jan-Mar
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
MDW > Montego Bay, Jamaica: Biz from $1075 Econ from $255. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Abuja, Nigeria: Biz from $3184 Econ from $954. – Jan-Mar (Including President’s Day Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Miami, Florida: Econ from $674. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Porto, Portugal: Econ from $485. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Salvador, El Salvador: Biz from $694 Econ from $179. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oslo, Norway: Econ from $441. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Jose, Costa Rica: Biz from $1227 Econ from $233. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sharjah, United Arab Emirates: Econ from $787. – Dec-Feb
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Denver, Colorado: Biz from $498 Econ from $38. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guadalajara, Mexico: Biz from $785 Econ from $211. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Krakow, Poland: Econ from $521. – Jan-Mar (Including President’s Day Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > New Orleans, Louisiana: Biz from $408. Econ from $94. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fort Myers, Florida: Econ from $62. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Aguadilla, Puerto Rico: Biz from $739. Econ from $145. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fort Lauderdale, Florida: Econ from $63. – Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Los Angeles, California: Econ from $118. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cartagena, Colombia: Biz from $919 Econ from $217. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Oranjestad, Aruba: Biz from $1113 Econ from $213. – Jan-Mar
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > San Pedro Sula, Honduras: Biz from $668 Econ from $234. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Austin, Texas: Econ from $98. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Montego Bay, Jamaica: Biz from $974 Econ from $243. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cluj Napoca, Romania: Econ from $540. – Jan-Mar (Including President’s Day Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Phoenix, Arizona: Econ from $60. – Jan-Mar
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Atlanta, Georgia: Biz from $428 Econ from $38. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Johannesburg, South Africa: Econ from $735. – Jan-Mar
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > San Jose, Costa Rica: Biz from $1192 Econ from $214. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Ontario, California: Econ from $118. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Abuja, Nigeria: Biz from $3198 Econ from $910. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Seattle, Washington: Biz from $498 Econ from $104. – Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Bucharest, Romania: Econ from $531. – Feb-Apr (Including Spring Break)
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Burbank, California: Econ from $80. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New York, New York: Biz from $382 Econ from $86. – Jan-Mar (Including President’s Day Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Miami, Florida: Econ from $58. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Marrakesh, Morocco: Econ from $481. – Jan-Mar
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Denver, Colorado: Econ from $40. – Feb-Apr
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1034 Econ from $223. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Myrtle Beach, South Carolina: Biz from $532 Econ from $123. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…