Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
![ORD > San Pedro Sula, Honduras: Biz from $832 Econ from $285. – Jun-Aug (Including Summer Break) ORD > San Pedro Sula, Honduras: Biz from $832 Econ from $285. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/happy-2723487_1280-1.jpg)
ORD > San Pedro Sula, Honduras: Biz from $832 Econ from $285. – Jun-Aug (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Durban, South Africa: Econ from $1017. – Apr-Jun ORD > Durban, South Africa: Econ from $1017. – Apr-Jun](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
ORD > Durban, South Africa: Econ from $1017. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
![ORD > Corfu, Greece: Econ from $672. – Jul-Sep ORD > Corfu, Greece: Econ from $672. – Jul-Sep](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Corfu, Greece: Econ from $672. – Jul-Sep
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
![ORD > Cartagena, Colombia: Biz from $869 Econ from $269. – Jul-Sep ORD > Cartagena, Colombia: Biz from $869 Econ from $269. – Jul-Sep](https://justgetoutoftown.com/wp-content/uploads/2017/10/park-2549989_1280.jpg)
ORD > Cartagena, Colombia: Biz from $869 Econ from $269. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Guatemala City, Guatemala: Biz from $807 Econ from $213. – Aug-Oct ORD > Guatemala City, Guatemala: Biz from $807 Econ from $213. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/cross-2536818_1280.jpg)
ORD > Guatemala City, Guatemala: Biz from $807 Econ from $213. – Aug-Oct
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: Biz from $437 Econ from $92. – Jul-Sep ORD > Myrtle Beach, South Carolina: Biz from $437 Econ from $92. – Jul-Sep](https://justgetoutoftown.com/wp-content/uploads/2017/10/beach-2405600_1280-1.jpg)
ORD > Myrtle Beach, South Carolina: Biz from $437 Econ from $92. – Jul-Sep
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![MDW > Punta Cana, Dominican Republic: Econ from $239. – Jun-Aug (Including Summer Break) MDW > Punta Cana, Dominican Republic: Econ from $239. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/dominican-republic-2828634_1280.jpg)
MDW > Punta Cana, Dominican Republic: Econ from $239. – Jun-Aug (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Thera, Greece: Econ from $654. – Apr-Jun ORD > Thera, Greece: Econ from $654. – Apr-Jun](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
ORD > Thera, Greece: Econ from $654. – Apr-Jun
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
![ORD > Montego Bay, Jamaica: Biz from $928 Econ from $253. – Aug-Oct ORD > Montego Bay, Jamaica: Biz from $928 Econ from $253. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/jamaica-679366_1280.jpg)
ORD > Montego Bay, Jamaica: Biz from $928 Econ from $253. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Bridgetown, Barbados: Econ from $259. – Aug-Oct MDW > Bridgetown, Barbados: Econ from $259. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/bridgetown-71375_1280.jpg)
MDW > Bridgetown, Barbados: Econ from $259. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Simpson Bay, St. Maarten: Econ from $315. – Aug-Oct ORD > Simpson Bay, St. Maarten: Econ from $315. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/sea-931165_1280.jpg)
ORD > Simpson Bay, St. Maarten: Econ from $315. – Aug-Oct
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 $48. – Aug-Oct MDW > Miami, Florida: Econ from $48. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/miami.jpg)
MDW > Miami, Florida: Econ from $48. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![MDW > Luqa, Malta: Econ from $532. – Nov-Jan (Including Thanksgiving) MDW > Luqa, Malta: Econ from $532. – Nov-Jan (Including Thanksgiving)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
MDW > Luqa, Malta: Econ from $532. – Nov-Jan (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
![ORD > Santo Domingo, Dominican Republic: Biz from $822 Econ from $272. – Aug-Oct ORD > Santo Domingo, Dominican Republic: Biz from $822 Econ from $272. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/iguanas-1887.jpg)
ORD > Santo Domingo, Dominican Republic: Biz from $822 Econ from $272. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $184. – Aug-Oct ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $184. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/FamilySCUBA-1.jpg)
ORD > Saint Thomas Island, U.S. Virgin Islands: Econ from $184. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Split, Croatia: Econ from $499. – Apr-Jun ORD > Split, Croatia: Econ from $499. – Apr-Jun](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Split, Croatia: Econ from $499. – Apr-Jun
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
![MDW > San Juan, Puerto Rico: Econ from $168. – May-Jul (Including Summer Break) MDW > San Juan, Puerto Rico: Econ from $168. – May-Jul (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/puerto-rico-1292633_1280.jpg)
MDW > San Juan, Puerto Rico: Econ from $168. – May-Jul (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Barcelona, Spain: Econ from $455. – Nov-Jan MDW > Barcelona, Spain: Econ from $455. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/barcelona-2626132_1280.jpg)
MDW > Barcelona, Spain: Econ from $455. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
![MDW > San Francisco, California: Econ from $78. – Aug-Oct MDW > San Francisco, California: Econ from $78. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/sebastien-gabriel-13686-1.jpg)
MDW > San Francisco, California: Econ from $78. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![MDW > San Salvador, El Salvador: Biz from $840 Econ from $280. – Aug-Oct (Including Labor Day) MDW > San Salvador, El Salvador: Biz from $840 Econ from $280. – Aug-Oct (Including Labor Day)](https://justgetoutoftown.com/wp-content/uploads/2017/10/el-salvador-2379443_1280.jpg)
MDW > San Salvador, El Salvador: Biz from $840 Econ from $280. – Aug-Oct (Including Labor Day)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Dubrovnik, Croatia: Econ from $547. – Sep-Nov (Including Fall Break) ORD > Dubrovnik, Croatia: Econ from $547. – Sep-Nov (Including Fall Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
ORD > Dubrovnik, Croatia: Econ from $547. – Sep-Nov (Including Fall Break)
* This is a “fare dump” with a few alternate dates available.
![ORD > Ponta Delgada, Portugal: Econ from $585. – Sep-Nov (Including Fall Break) ORD > Ponta Delgada, Portugal: Econ from $585. – Sep-Nov (Including Fall Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/lisbon-1653086_1280.jpg)
ORD > Ponta Delgada, Portugal: Econ from $585. – Sep-Nov (Including Fall Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
![ORD > Colombo, Sri Lanka: Econ from $895. – Mar-May ORD > Colombo, Sri Lanka: Econ from $895. – Mar-May](https://justgetoutoftown.com/wp-content/uploads/2017/10/fishermen-219161_1280.jpg)
ORD > Colombo, Sri Lanka: Econ from $895. – Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
![ORD > Heraklion, Greece: Econ from $602. – Sep-Nov (Including Fall Break) ORD > Heraklion, Greece: Econ from $602. – Sep-Nov (Including Fall Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
ORD > Heraklion, Greece: Econ from $602. – Sep-Nov (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
![ORD > Georgetown, Guyana: Biz from $1025 Econ from $622. – Aug-Oct ORD > Georgetown, Guyana: Biz from $1025 Econ from $622. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
ORD > Georgetown, Guyana: Biz from $1025 Econ from $622. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
![ORD > Buenos Aires, Argentina: Biz from $2690 Econ from $812. – Jun-Aug (Including Summer Break) ORD > Buenos Aires, Argentina: Biz from $2690 Econ from $812. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
ORD > Buenos Aires, Argentina: Biz from $2690 Econ from $812. – Jun-Aug (Including Summer Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
![ORD > Tampa, Florida: Econ from $78. – Aug-Oct ORD > Tampa, Florida: Econ from $78. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/canoe-2246464_1280.jpg)
ORD > Tampa, Florida: Econ from $78. – Aug-Oct
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: Biz from $427 Econ from $79. – Aug-Oct ORD > Myrtle Beach, South Carolina: Biz from $427 Econ from $79. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/light-house-2670889_1280.jpg)
ORD > Myrtle Beach, South Carolina: Biz from $427 Econ from $79. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![ORD > San Pedro Sula, Honduras: Biz from $737 Econ from $200. – Aug-Oct ORD > San Pedro Sula, Honduras: Biz from $737 Econ from $200. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/roatan-1358175_1280.jpg)
ORD > San Pedro Sula, Honduras: Biz from $737 Econ from $200. – Aug-Oct
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: Biz from $951 Econ from $229. – Jun-Aug (Including Summer Break) MDW > Punta Cana, Dominican Republic: Biz from $951 Econ from $229. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/beach-15208_1280.jpg)
MDW > Punta Cana, Dominican Republic: Biz from $951 Econ from $229. – Jun-Aug (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Corfu, Greece: Econ from $682. – Jul-Sep ORD > Corfu, Greece: Econ from $682. – Jul-Sep](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Corfu, Greece: Econ from $682. – Jul-Sep
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
![ORD > Durban, South Africa: Econ from $1015. – Sep-Nov (Including Fall Break) ORD > Durban, South Africa: Econ from $1015. – Sep-Nov (Including Fall Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
ORD > Durban, South Africa: Econ from $1015. – Sep-Nov (Including Fall Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
![ORD > Oranjestad, Aruba: Biz from $1106 Econ from $306. – Aug-Oct ORD > Oranjestad, Aruba: Biz from $1106 Econ from $306. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/Aruba-Jochelle.jpg)
ORD > Oranjestad, Aruba: Biz from $1106 Econ from $306. – Aug-Oct
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
![ORD > Cartagena, Colombia: Biz from $829 Econ from $239. – Aug-Oct ORD > Cartagena, Colombia: Biz from $829 Econ from $239. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/park-2549989_1280.jpg)
ORD > Cartagena, Colombia: Biz from $829 Econ from $239. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Guatemala City, Guatemala: Biz from $698 Econ from $213. – Jul-Sep ORD > Guatemala City, Guatemala: Biz from $698 Econ from $213. – Jul-Sep](https://justgetoutoftown.com/wp-content/uploads/2017/10/bus-891920_1280.jpg)
ORD > Guatemala City, Guatemala: Biz from $698 Econ from $213. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Boston, Massachusetts: Biz from $447 Econ from $136. – Aug-Oct (Including Labor Day) MDW > Boston, Massachusetts: Biz from $447 Econ from $136. – Aug-Oct (Including Labor Day)](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
MDW > Boston, Massachusetts: Biz from $447 Econ from $136. – Aug-Oct (Including Labor Day)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > Puerto Vallarta, Mexico: Econ from $275. – Jan-Mar ORD > Puerto Vallarta, Mexico: Econ from $275. – Jan-Mar](https://justgetoutoftown.com/wp-content/uploads/2017/10/tzotzil-maya-1736335_1280.jpg)
ORD > Puerto Vallarta, Mexico: Econ from $275. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Simpson Bay, St. Maarten: Econ from $259. – Aug-Oct ORD > Simpson Bay, St. Maarten: Econ from $259. – Aug-Oct](https://justgetoutoftown.com/wp-content/uploads/2017/10/hawaii-1037024_1280.jpg)
ORD > Simpson Bay, St. Maarten: Econ from $259. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $988 Econ from $215. – Jun-Aug (Including Summer Break) ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $988 Econ from $215. – Jun-Aug (Including Summer Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/nassau-2444243_1280.jpg)
ORD > Saint Thomas Island, U.S. Virgin Islands: Biz from $988 Econ from $215. – Jun-Aug (Including Summer Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…