Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cairo, Egypt: Econ from $803. – Nov-Jan (Including Winter Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Barcelona, Spain: Econ from $517. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: Econ from $566. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Warsaw, Poland: Econ from $511. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Bucharest, Romania: Econ from $493. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Gdansk, Poland: Econ from $463. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dubai, United Arab Emirates: Econ from $695. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Reykjavik, Iceland: Econ from $397. – Nov-Jan (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Asheville, North Carolina: Econ from $79. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Atlantic City, New Jersey: Econ from $58. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Dallas, Texas: Biz from $507 Econ from $48. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Philadelphia, Pennsylvania: Econ from $38. – Nov-Jan
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Hartford, Connecticut: Biz from $468 Econ from $158. – Nov-Jan
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > San Francisco, California: Econ from $78. – Nov-Jan
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Reno, Nevada: Econ from $150. – Nov-Jan
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
MDW > Asheville, North Carolina: Econ from $77. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Ontario, California: Econ from $88. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > San Juan, Puerto Rico: Biz from $834 Econ from $87. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cincinnati, Ohio: Biz from $338 Econ from $110. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Richmond, Virginia: Econ from $120. – Nov-Jan
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. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Armenia, Colombia: Econ from $298. – Nov-Jan
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: Biz from $660 Econ from $138. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Portland, Oregon: Econ from $118. – Nov-Jan
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 $1026 Econ from $224. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Boston, Massachusetts: Biz from $448 Econ from $98. – Nov-Jan
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Liberia, Costa Rica: Biz from $1323 Econ from $282. – Nov-Jan
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
MDW > San Diego, California: Econ from $88. – Nov-Jan
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 $944 Econ from $277. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Phoenix, Arizona: Econ from $58. – Nov-Jan
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
MDW > Atlanta, Georgia: Biz from $418 Econ from $34. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Salt Lake City, Utah: Econ from $88. – Nov-Jan
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Tunis, Tunisia: Biz from $2557 Econ from $729. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > San Francisco, California: Econ from $78. – Nov-Jan
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Cartagena, Colombia: Biz from $941 Econ from $211. – Nov-Jan
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Boise, Idaho: Econ from $129. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Montego Bay, Jamaica: Biz from $970 Econ from $250. – Nov-Jan
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 $88. – Nov-Jan
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Tokyo, Japan: Econ from $569. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…