Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Malaga, Spain: Econ from $528. – 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 > Colombo, Sri Lanka: Econ from $895. – 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 > Dublin, Ireland: Econ from $425. – 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 > Porto, Portugal: Econ from $494. – Dec-Feb
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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…
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,…
MDW > San Diego, California: Econ from $106. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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.…
ORD > Fort Lauderdale, Florida: Econ from $64. – Jan-Mar
Have you ever booked a cruise only to find out that the flight to get there was going to be…
MDW > Phoenix, Arizona: Econ from $76. – Jan-Mar
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Baltimore, Maryland: Econ from $77. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Norfolk, Virginia: Biz from $505 Econ from $92. – 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 > Newark, New Jersey: Biz from $401 Econ from $84. – Dec-Feb
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 $676 Econ from $232. – Jan-Mar
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 $102. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Burbank, California: Econ from $149. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Guatemala City, Guatemala: Biz from $815 Econ from $187. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Christiansted, U.S. Virgin Islands: Econ from $184. – Jan-Mar
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 $148. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Georgetown, Guyana: Biz from $855 Econ from $395. – Dec-Feb
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Simpson Bay, St. Maarten: 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 > Hartford, Connecticut: Biz from $548 Econ from $95. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Kingston, Jamaica: Biz from $696 Econ from $295. – Dec-Feb
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 $368 Econ from $134. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Punta Cana, Dominican Republic: Biz from $824 Econ from $239. – Jan-Mar
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 $505 Econ from $98. – Dec-Feb
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
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 > Seattle, Washington: Biz from $628 Econ from $118. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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 > Cancun, Mexico: Biz from $652 Econ from $157. – Dec-Feb
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 $388 Econ from $83. – Dec-Feb
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Houston, Texas: Econ from $98. – Dec-Feb
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Pristina, Kosovo: Econ from $630. – Dec-Feb
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 $697 Econ from $117. – Dec-Feb
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 $56. – 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 > Atlanta, Georgia: Biz from $388 Econ from $36. – Dec-Feb
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Managua, Nicaragua: Biz from $1140 Econ from $186. – Dec-Feb
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Baltimore, Maryland: Econ from $78. – Dec-Feb
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…