Have friends or family in Fort Myers? Grab this cheap flight and visit them, or check out the reverse search…
ORD > Panama City, Panama: $303 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Atlanta, Georgia: $125 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in Atlanta? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Houston, Texas: $90 round-trip – Apr-Jun (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 > Guadalajara, Mexico: $239 round-trip – Jun-Aug (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 > Dublin, Ireland: $395 round-trip – Jul-Sep (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
MDW > Cincinnati, Ohio: $196 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in Cincinnati? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Baltimore, Maryland: $131 round-trip – Apr-Jun (Including Summer Break) [SOLD OUT]
Have friends or family in Baltimore? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Juneau, Alaska: $341 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > Nashville, Tennessee: $29 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > Managua, Nicaragua: $394 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > New Haven, Connecticut: $168 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in New Haven? Grab this cheap flight and visit them, or check out the reverse search…
ORD > Guayaquil, Ecuador: $412 round-trip -May-Jul (Including Summer Break) [SOLD OUT]
* This is a “fare dump” with a few alternate dates available.
ORD > San Salvador, El Salvador: $329 round-trip – Apr-Jun (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 > Seattle, Washington: $159 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in Seattle? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > George Town, Cayman Islands: $384 round-trip – Jun-Aug (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 > Minneapolis, Minnesota: $77 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in Minneapolis? Grab this cheap flight and visit them, or check out the reverse search link…
MDW > Toronto, Canada: $229 round-trip – May-Jul (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 > Managua, Nicaragua: $370 round-trip – May-Jul (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 > Atlanta, Georgia: $113 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in Atlanta? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Bogota, Colombia: $275 round-trip – Apr-Jun (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 > San Diego, California: $169 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in San Diego? Grab this cheap flight and visit them, or check out the reverse search…
ORD > Nashville, Tennessee: $87 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
Have friends or family in Nashville? Grab this cheap flight and visit them, or check out the reverse search link…
ORD > Punta Cana, Dominican Republic: $310 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 > Boston, Massachusetts: $96 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Reykjavik, Iceland: $522 round-trip – Jun-Aug (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 > George Town, Cayman Islands: $392 round-trip – May-Jul (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…
MDW > Toronto, Canada: $201 round-trip – May-Jul (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 > Lima, Peru: $401 round-trip – May-Jul (Including Summer Break) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…