Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Toronto, Canada: Econ from $264. – 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 > Dubrovnik, Croatia: From $473 round-trip – Jun-Aug (Including Fourth of July) *BB [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Budapest, Hungary: From $397 round-trip – Jun-Aug (Including Fourth of July) *BB [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 > Bilbao, Spain: From $338 round-trip – Jun-Aug (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 > Budapest, Hungary: From $420 round-trip – Jun-Aug (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 > 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 > 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 > 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 > 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…
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…
ORD > Baltimore, Maryland: From $49 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…
ORD > San Diego, California: From $75 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 > New Orleans, Louisiana: From $34 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 > Guadalajara, Mexico: From $219 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.…
MDW > Knoxville, Tennessee: From $42 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 > Tampa, Florida: From $49 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 > Curitiba, Brazil: From $546 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Panama City, Panama: From $253 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Portland, Oregon: From $114 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 > Atlanta, Georgia: From $49 round-trip – Jun-Aug (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 > Dallas, Texas: From $67 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Dallas? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Fort Lauderdale, Florida: From $76 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 > Christiansted, U.S. Virgin Islands: From $217 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Austin, Texas: From $49 round-trip – Jun-Aug (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 > Florianopolis, Brazil: From $538 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available. Chicago to Florianopolis, Brazil Want to book this…
ORD > Oakland, California: From $84 round-trip – Jun-Aug (Including Fourth of July) [SOLD OUT]
Have friends or family in Oakland? Grab this cheap flight and visit them, or check out the reverse search link…
MDW > Asheville, North Carolina: From $42 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Asheville? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Brasilia, Brazil: From $541 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Manchester, New Hampshire: From $97 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Manchester? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Sacramento, California: From $86 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family in Sacramento? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Cancun, Mexico: From $144 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Premium subscriber benefit: Log in and click below to download a 6-night luxury vacation voucher for Mayan Palace in Mazatlan,…
ORD > Boston, Massachusetts: From $48 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
Have friends or family in Boston? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Los Angeles, California: From $53 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 > Houston, Texas: From $140 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Houston? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Orlando, Florida: From $69 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Orlando? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Allentown, Pennsylvania: From $59 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Allentown? Grab this cheap flight and visit them, or check out the reverse search link…
MDW > Savannah, Georgia: From $57 round-trip – Jun-Aug (Including Summer Break) [SOLD OUT]
Have friends or family in Savannah? Grab this cheap flight and visit them, or check out the reverse search link…