Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Punta Cana, Dominican Republic: Econ from $250. – May-Jul (Including Summer Break) MDW > Punta Cana, Dominican Republic: Econ from $250. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/dominican-republic-2828634_1280.jpg)
MDW > Punta Cana, Dominican Republic: Econ from $250. – May-Jul (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 > Santiago, Chile: Econ from $546. – May-Jul (Including Summer Break) ORD > Santiago, Chile: Econ from $546. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/aircraft-513641_640.jpg)
ORD > Santiago, Chile: Econ from $546. – 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 > San Pedro Sula, Honduras: Biz from $776 Econ from $305. – Apr-Jun (Including Summer Break) ORD > San Pedro Sula, Honduras: Biz from $776 Econ from $305. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/happy-2723487_1280-1.jpg)
ORD > San Pedro Sula, Honduras: Biz from $776 Econ from $305. – Apr-Jun (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 > Cali, Colombia: Econ from $364. – Apr-Jun (Including Summer Break) ORD > Cali, Colombia: Econ from $364. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/lighthouse-2516803_1280.jpg)
ORD > Cali, Colombia: Econ from $364. – Apr-Jun (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 > San Diego, California: Econ from $165. – May-Jul (Including Summer Break) MDW > San Diego, California: Econ from $165. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/pelican-2225050_1280.jpg)
MDW > San Diego, California: Econ from $165. – May-Jul (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 > Monterrey, Mexico: Econ from $246. – Apr-Jun (Including Summer Break) ORD > Monterrey, Mexico: Econ from $246. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/monterrey-555080_1280.jpg)
ORD > Monterrey, Mexico: Econ from $246. – Apr-Jun (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 > San Jose, Costa Rica: Econ from $295. – May-Jul (Including Summer Break) MDW > San Jose, Costa Rica: Econ from $295. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/Costa-Rica-Taken-By-Joel-McDonald.jpg)
MDW > San Jose, Costa Rica: Econ from $295. – May-Jul (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: Econ from $78. – May-Jul (Including Summer Break) MDW > Knoxville, Tennessee: Econ from $78. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/rafting-421132_1280.jpg)
MDW > Knoxville, Tennessee: Econ from $78. – May-Jul (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…
![MDW > San Francisco, California: Econ from $140. – Apr-Jun (Including Summer Break) MDW > San Francisco, California: Econ from $140. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/sebastien-gabriel-13686-1.jpg)
MDW > San Francisco, California: Econ from $140. – Apr-Jun (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…
![MDW > Toronto, Canada: Biz from $626 Econ from $194. – May-Jul (Including Summer Break) MDW > Toronto, Canada: Biz from $626 Econ from $194. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
MDW > Toronto, Canada: Biz from $626 Econ from $194. – May-Jul (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: Econ from $97. – Jun-Aug (Including Summer Break) MDW > Knoxville, Tennessee: Econ from $97. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/chattanooga-1719772_1280.jpg)
MDW > Knoxville, Tennessee: Econ from $97. – 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 > Split, Croatia: Econ from $611. – Jul-Sep (Including Summer Break) ORD > Split, Croatia: Econ from $611. – Jul-Sep (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Split, Croatia: Econ from $611. – 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…
![MDW > Knoxville, Tennessee: Econ from $93. – May-Jul (Including Summer Break) MDW > Knoxville, Tennessee: Econ from $93. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/rafting-421132_1280.jpg)
MDW > Knoxville, Tennessee: Econ from $93. – May-Jul (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 > Cape Town, South Africa: Econ from $974. – May-Jul (Including Summer Break) ORD > Cape Town, South Africa: Econ from $974. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/aircraft-513641_640.jpg)
ORD > Cape Town, South Africa: Econ from $974. – 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 > Merida, Mexico: Biz from $721 Econ from $264. – Apr-Jun (Including Summer Break) ORD > Merida, Mexico: Biz from $721 Econ from $264. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/beach-2392402_1280.jpg)
ORD > Merida, Mexico: Biz from $721 Econ from $264. – Apr-Jun (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 > Palanga, Lithuania: Econ from $627. – May-Jul (Including Summer Break) ORD > Palanga, Lithuania: Econ from $627. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
ORD > Palanga, Lithuania: Econ from $627. – 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 > Palanga, Lithuania: Econ from $677. – May-Jul (Including Summer Break) ORD > Palanga, Lithuania: Econ from $677. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
ORD > Palanga, Lithuania: Econ from $677. – May-Jul (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 > Palanga, Lithuania: Econ from $663. – May-Jul (Including Summer Break) ORD > Palanga, Lithuania: Econ from $663. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Palanga, Lithuania: Econ from $663. – May-Jul (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 > Vienna, Austria: Econ from $511. – Apr-Jun (Including Summer Break) ORD > Vienna, Austria: Econ from $511. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
ORD > Vienna, Austria: Econ from $511. – Apr-Jun (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…
![MDW > New Haven, Connecticut: Biz from $508 Econ from $156. – Jul-Sep (Including Summer Break) MDW > New Haven, Connecticut: Biz from $508 Econ from $156. – Jul-Sep (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/aircraft-513641_640.jpg)
MDW > New Haven, Connecticut: Biz from $508 Econ from $156. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![MDW > Dallas, Texas: Econ from $128. – Jul-Sep (Including Summer Break) MDW > Dallas, Texas: Econ from $128. – Jul-Sep (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
MDW > Dallas, Texas: Econ from $128. – Jul-Sep (Including Summer Break) [SOLDOUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![MDW > Philadelphia, Pennsylvania: Econ from $120. – Jun-Aug (Including Summer Break) MDW > Philadelphia, Pennsylvania: Econ from $120. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
MDW > Philadelphia, Pennsylvania: Econ from $120. – Jun-Aug (Including Summer Break) [SOLDOUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![MDW > Toronto, Canada: Biz from $555 Econ from $164. – Jun-Aug (Including Summer Break) MDW > Toronto, Canada: Biz from $555 Econ from $164. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
MDW > Toronto, Canada: Biz from $555 Econ from $164. – Jun-Aug (Including Summer Break) [SOLDOUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
![ORD > Hartford, Connecticut: Biz from $505 Econ from $164. – Jun-Aug (Including Fourth of July and Summer Break) ORD > Hartford, Connecticut: Biz from $505 Econ from $164. – Jun-Aug (Including Fourth of July and Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
ORD > Hartford, Connecticut: Biz from $505 Econ from $164. – Jun-Aug (Including Fourth of July and Summer Break) [SOLDOUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > New Orleans, Louisiana: Econ from $87. – Jun-Aug (Including Summer Break) ORD > New Orleans, Louisiana: Econ from $87. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/crawfish-2606517_1280.jpg)
ORD > New Orleans, Louisiana: Econ from $87. – Jun-Aug (Including Summer Break) [SOLDOUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
![ORD > Paris, France: Econ from $430. – Apr-Jun (Including Summer Break) ORD > Paris, France: Econ from $430. – Apr-Jun (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/fontainebleau-2540239_1280.jpg)
ORD > Paris, France: Econ from $430. – Apr-Jun (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 > Philadelphia, Pennsylvania: Econ from $115. – Jun-Aug (Including Fourth of July and Summer Break) ORD > Philadelphia, Pennsylvania: Econ from $115. – Jun-Aug (Including Fourth of July and Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Philadelphia, Pennsylvania: Econ from $115. – Jun-Aug (Including Fourth of July and Summer Break) [SOLDOUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > Dallas, Texas: Econ from $163. – May-Jul (Including Summer Break) ORD > Dallas, Texas: Econ from $163. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
ORD > Dallas, Texas: Econ from $163. – May-Jul (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 > New York, New York: Biz from $433. Econ from $172. – May-Jul (Including Summer Break) ORD > New York, New York: Biz from $433. Econ from $172. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/New-York-by-Joel-McDonald.jpg)
ORD > New York, New York: Biz from $433. Econ from $172. – May-Jul (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 > Myrtle Beach, South Carolina: Econ from $86. – May-Jul (Including Summer Break) ORD > Myrtle Beach, South Carolina: Econ from $86. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/beach-2405600_1280-1.jpg)
ORD > Myrtle Beach, South Carolina: Econ from $86. – May-Jul (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 > Hartford, Connecticut: Biz from $666. Econ from $180. – May-Jul (Including Summer Break) ORD > Hartford, Connecticut: Biz from $666. Econ from $180. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
ORD > Hartford, Connecticut: Biz from $666. Econ from $180. – May-Jul (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 > Miami, Florida: Econ from $86. – May-Jul (Including Summer Break) ORD > Miami, Florida: Econ from $86. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/cruise-ship-2251245_1280.jpg)
ORD > Miami, Florida: Econ from $86. – May-Jul (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…
![MDW > Toronto, Canada: Biz from $506 Econ from $118. – May-Jul (Including Summer Brea MDW > Toronto, Canada: Biz from $506 Econ from $118. – May-Jul (Including Summer Brea](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
MDW > Toronto, Canada: Biz from $506 Econ from $118. – May-Jul (Including Summer Brea [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
![MDW > Philadelphia, Pennsylvania: Econ from $103. – May-Jul (Including Summer Break) MDW > Philadelphia, Pennsylvania: Econ from $103. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
MDW > Philadelphia, Pennsylvania: Econ from $103. – May-Jul (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…
![MDW > Savannah, Georgia: Econ from $128. – Jun-Aug (Including Fourth of July and Summer Break) MDW > Savannah, Georgia: Econ from $128. – Jun-Aug (Including Fourth of July and Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/aircraft-513641_640.jpg)
MDW > Savannah, Georgia: Econ from $128. – Jun-Aug (Including Fourth of July and Summer Break) [SOLDOUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > New Orleans, Louisiana: Econ from $124. – May-Jul (Including Summer Break) ORD > New Orleans, Louisiana: Econ from $124. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/crawfish-2606517_1280.jpg)
ORD > New Orleans, Louisiana: Econ from $124. – May-Jul (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 > Ottawa, Canada: from $205. – May-Jul (Including Summer Break) MDW > Ottawa, Canada: from $205. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
MDW > Ottawa, Canada: from $205. – May-Jul (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: Econ from $174. – May-Jul (Including Summer Break) ORD > Dallas, Texas: Econ from $174. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
ORD > Dallas, Texas: Econ from $174. – May-Jul (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…
![MDW > Quebec City, Canada: Econ from $246. – May-Jul (Including Summer Break) MDW > Quebec City, Canada: Econ from $246. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/frontenac-2257154_1280.jpg)
MDW > Quebec City, Canada: Econ from $246. – May-Jul (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.…