Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Helsinki, Finland: From $361 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Budapest, Hungary: From $418 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Moscow, Russia: From $448 round-trip – Apr-Jun (Including Summer Break) *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Burbank, California: From $93 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Seattle, Washington: From $74 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Fairbanks, Alaska: From $322 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Austin, Texas: From $29 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
JGOOT Subscriber tells us about his $97 round-trip direct flight to Austin (that he has paid $350 for in the…
ORD > Denver, Colorado: From $35 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…
ORD > Port Au Prince, Haiti: From $206 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sacramento, California: From $68 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Boston, Massachusetts: From $27 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Atlantic City, New Jersey: From $90 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Orlando, Florida: From $49 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > San Salvador, El Salvador: From $157 round-trip – Jul-Sep (Including Summer Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Philadelphia, Pennsylvania: From $57 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > New York, New York: From $67 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Fort Myers, Florida: From $72 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Raleigh, North Carolina: From $58 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Atlanta, Georgia: From $28 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Buffalo, New York: From $97 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Austin, Texas: From $40 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Kingston, Jamaica: From $270 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Denver, Colorado: From $73 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Guayaquil, Ecuador: From $229 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Sacramento, California: From $88 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Boston, Massachusetts: From $32 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Guatemala City, Guatemala: From $200 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
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: From $82 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Jacksonville, Florida: From $88 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > San Salvador, El Salvador: From $213 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Orlando, Florida: From $53 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cancun, Mexico: From $134 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Kansas City, Kansas: From $91 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cincinnati, Ohio: From $97 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
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: From $57 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Washington, DC: From $50 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Savannah, Georgia: From $69 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Managua, Nicaragua: From $262 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Hartford, Connecticut: From $190 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…