Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > San Diego, California: Econ from $151.- Dec-Feb (Including MLK Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Orlando, Florida: Econ from $58.- Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Managua, Nicaragua: Biz from $436 Econ from $211.- 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.…
MDW > Newark, New Jersey: Econ from $53. – Dec-Feb (Including MLK Weekend)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
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 > 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 > 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 > 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 > 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 > San Diego, California: Econ from $122.- 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 > Philadelphia, Pennsylvania: Biz from $263 Econ from $61.- 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 > Baltimore, Maryland: Biz from $297 Econ from $58. – 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 > Liberia, Costa Rica: Biz from $976 Econ from $345.- Dec-Feb (Including MLK Weekend)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
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…
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.…
MDW > Miami, Florida: Econ from $57.- 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 > 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 > Boston, Massachusetts: Biz from $343 Econ from $110.- Dec-Feb (Including MLK Weekend)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Houston, Texas: Biz from $286 Econ from $57.- 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 > Atlanta, Georgia: Biz from $249 Econ from $57.- 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 > 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 > 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 > Montego Bay, Jamaica: Biz from $610 Econ from $298.- 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 > Cancun, Mexico: Biz from $501 Econ from $187.- 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 > San Diego, California: Econ from $103.- Dec-Feb (Including MLK Weekend)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Orlando, Florida: Econ from $54.- Dec-Feb (Including MLK Weekend)
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Punta Cana, Dominican Republic: Biz from $770 Econ from $205. – 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.…