Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Belgrade, Serbia: Econ from $544. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Bogota, Colombia: Biz from $926 Econ from $218. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Newark, New Jersey: Biz from $401 Econ from $87. – Jan-Mar
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > San Salvador, El Salvador: Biz from $721 Econ from $185. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Simpson Bay, St. Maarten: Econ from $247. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Atlantic City, New Jersey: Econ from $130. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Denver, Colorado: Biz from $499 Econ from $58. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $1078 Econ from $178. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Madrid, Spain: Econ from $466. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Burbank, California: Econ from $127. – Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Montego Bay, Jamaica: Biz from $973 Econ from $252. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Nashville, Tennessee: Biz from $375 Econ from $96. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Boise, Idaho: Biz from $638 Econ from $156. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Casablanca, Morocco: Econ from $482. – Jan-Mar (Including President’s Day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Christiansted, U.S. Virgin Islands: Econ from $180. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Porto, Portugal: Econ from $475. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dallas, Texas: Biz from $429 Econ from $61. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Santo Domingo, Dominican Republic: Biz from $836 Econ from $243. – Jan-Mar (Including President’s Day Weekend)
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: Econ from $123. – Jan-Mar (Including President’s Day Weekend)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Cancun, Mexico: Biz from $689 Econ from $165. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Kingston, Jamaica: Biz from $698 Econ from $296. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Tirana, Albania: Biz from $2592 Econ from $571. – 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 > Krakow, Poland: Econ from $510. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cincinnati, Ohio: Biz from $369 Econ from $125. – Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Boston, Massachusetts: Biz from $377 Econ from $98. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Punta Cana, Dominican Republic: Biz from $751 Econ from $229. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Houston, Texas: Econ from $97. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Cluj Napoca, Romania: Econ from $561. – Jan-Mar (Including President’s Day Weekend)
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
MDW > Miami, Florida: Econ from $64. – 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 > Riga, Latvia: Econ from $524. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Omaha, Nebraska: Biz from $504 Econ from $123. – Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Santa Ana, California: Econ from $106. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Oranjestad, Aruba: Biz from $1044 Econ from $219. – Jan-Mar (Including President’s Day Weekend)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Guayaquil, Ecuador: Biz from $1133 Econ from $244. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Pedro Sula, Honduras: Biz from $624 Econ from $229. – 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 (Including President’s Day Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Atlanta, Georgia: Biz from $479 Econ from $61. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Abuja, Nigeria: Biz from $3317 Econ from $991. – Feb-Apr
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: Biz from $887 Econ from $126. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…