Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Mexico City, Mexico: Econ from $215. – Nov-Jan ORD > Mexico City, Mexico: Econ from $215. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/day-of-the-dead-2229334_1280.jpg)
ORD > Mexico City, Mexico: Econ from $215. – Nov-Jan
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
![MDW > Wroclaw, Poland: Econ from $467. – Nov-Jan (Including Thanksgiving) MDW > Wroclaw, Poland: Econ from $467. – Nov-Jan (Including Thanksgiving)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
MDW > Wroclaw, Poland: Econ from $467. – Nov-Jan (Including Thanksgiving)
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
![ORD > Marrakesh, Morocco: Econ from $595. – Nov-Jan (Including Thanksgiving) ORD > Marrakesh, Morocco: Econ from $595. – Nov-Jan (Including Thanksgiving)](https://justgetoutoftown.com/wp-content/uploads/2017/10/morocco-1046535_1280.jpg)
ORD > Marrakesh, Morocco: Econ from $595. – Nov-Jan (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
![MDW > Guadalajara, Mexico: Econ from $213. – Oct-Dec MDW > Guadalajara, Mexico: Econ from $213. – Oct-Dec](https://justgetoutoftown.com/wp-content/uploads/2017/10/mexico-1323559_1280.jpg)
MDW > Guadalajara, Mexico: Econ from $213. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Jeddah, Saudi Arabia: Econ from $958. – Nov-Jan (Including Thanksgiving) MDW > Jeddah, Saudi Arabia: Econ from $958. – Nov-Jan (Including Thanksgiving)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
MDW > Jeddah, Saudi Arabia: Econ from $958. – Nov-Jan (Including Thanksgiving)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
![ORD > Cozumel, Mexico: Biz from $1096 Econ from $294. – Nov-Jan ORD > Cozumel, Mexico: Biz from $1096 Econ from $294. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/diving-689831_1280.jpg)
ORD > Cozumel, Mexico: Biz from $1096 Econ from $294. – Nov-Jan
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
![MDW > Philadelphia, Pennsylvania: Econ from $80. – Nov-Jan (Including Winter Break) MDW > Philadelphia, Pennsylvania: Econ from $80. – Nov-Jan (Including Winter Break)](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
MDW > Philadelphia, Pennsylvania: Econ from $80. – Nov-Jan (Including Winter 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 > New York, New York: Biz from $392 Econ from $162. – Nov-Jan ORD > New York, New York: Biz from $392 Econ from $162. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/New-York-2.jpg)
ORD > New York, New York: Biz from $392 Econ from $162. – Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > Hartford, Connecticut: Biz from $436 Econ from $78. – Nov-Jan ORD > Hartford, Connecticut: Biz from $436 Econ from $78. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/aircraft-513641_640.jpg)
ORD > Hartford, Connecticut: Biz from $436 Econ from $78. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![MDW > Ontario, California: Econ from $120. – Nov-Jan MDW > Ontario, California: Econ from $120. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
MDW > Ontario, California: Econ from $120. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![MDW > Fort Lauderdale, Florida: Econ from $75. – Nov-Jan MDW > Fort Lauderdale, Florida: Econ from $75. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/miami-2690191_1280.jpg)
MDW > Fort Lauderdale, Florida: Econ from $75. – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
![ORD > Houston, Texas: Econ from $93. – Nov-Jan ORD > Houston, Texas: Econ from $93. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/houston-1238154_1280.jpg)
ORD > Houston, Texas: Econ from $93. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![ORD > Miami, Florida: Econ from $75. – Nov-Jan ORD > Miami, Florida: Econ from $75. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/cruise-ship-2251245_1280.jpg)
ORD > Miami, Florida: Econ from $75. – Nov-Jan [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: Biz from $659 Econ from $166. – Nov-Jan ORD > Seattle, Washington: Biz from $659 Econ from $166. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/seattle-1037404_1280.jpg)
ORD > Seattle, Washington: Biz from $659 Econ from $166. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![ORD > Baltimore, Maryland: Econ from $93. – Nov-Jan ORD > Baltimore, Maryland: Econ from $93. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/luggage-1436515_640.jpg)
ORD > Baltimore, Maryland: Econ from $93. – Nov-Jan [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 > Portland, Oregon: Econ from $162. – Nov-Jan ORD > Portland, Oregon: Econ from $162. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
ORD > Portland, Oregon: Econ from $162. – Nov-Jan [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
![ORD > Las Vegas, Nevada: Econ from $61. – Nov-Jan ORD > Las Vegas, Nevada: Econ from $61. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/usa-2650170_1280.jpg)
ORD > Las Vegas, Nevada: Econ from $61. – Nov-Jan [SOLD OUT]
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…
![ORD > San Diego, California: Econ from $115. – Nov-Jan ORD > San Diego, California: Econ from $115. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/skydivers-81778_1280.jpg)
ORD > San Diego, California: Econ from $115. – Nov-Jan [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
![MDW > Atlanta, Georgia: Econ from $74. – Nov-Jan (Including Winter Break) MDW > Atlanta, Georgia: Econ from $74. – Nov-Jan (Including Winter Break)](https://justgetoutoftown.com/wp-content/uploads/2017/10/pemberton-statue-844765_1280.jpg)
MDW > Atlanta, Georgia: Econ from $74. – Nov-Jan (Including Winter 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 > Sacramento, California: Econ from $138. – Nov-Jan MDW > Sacramento, California: Econ from $138. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
MDW > Sacramento, California: Econ from $138. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
![ORD > New York, New York: Biz from $392 Econ from $129. – Nov-Jan ORD > New York, New York: Biz from $392 Econ from $129. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/New-York1.jpg)
ORD > New York, New York: Biz from $392 Econ from $129. – Nov-Jan [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
![MDW > Toronto, Canada: Biz from $254 Econ from $189. – Nov-Jan MDW > Toronto, Canada: Biz from $254 Econ from $189. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/aircraft-513641_640.jpg)
MDW > Toronto, Canada: Biz from $254 Econ from $189. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Philadelphia, Pennsylvania: Econ from $69. – Nov-Jan MDW > Philadelphia, Pennsylvania: Econ from $69. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
MDW > Philadelphia, Pennsylvania: Econ from $69. – Nov-Jan [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
![MDW > Los Angeles, California: Econ from $128. – Nov-Jan MDW > Los Angeles, California: Econ from $128. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/hollywood-sign-1598473_1280-1.jpg)
MDW > Los Angeles, California: Econ from $128. – Nov-Jan [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
![ORD > San Juan, Puerto Rico: Econ from $184. – Nov-Jan ORD > San Juan, Puerto Rico: Econ from $184. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/cristian-escobar-287262.jpg)
ORD > San Juan, Puerto Rico: Econ from $184. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Denver, Colorado: Econ from $59. – Nov-Jan MDW > Denver, Colorado: Econ from $59. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/denver-1567052_1280.jpg)
MDW > Denver, Colorado: Econ from $59. – Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > Dallas, Texas: Biz from $445 Econ from $76. – Nov-Jan ORD > Dallas, Texas: Biz from $445 Econ from $76. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
ORD > Dallas, Texas: Biz from $445 Econ from $76. – Nov-Jan [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 > Montego Bay, Jamaica: Biz from $1,045 Econ from $247. – Nov-Jan ORD > Montego Bay, Jamaica: Biz from $1,045 Econ from $247. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/beach-1029014_1280.jpg)
ORD > Montego Bay, Jamaica: Biz from $1,045 Econ from $247. – Nov-Jan [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: Econ from $179. – Nov-Jan ORD > Myrtle Beach, South Carolina: Econ from $179. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/beach-2405600_1280-1.jpg)
ORD > Myrtle Beach, South Carolina: Econ from $179. – Nov-Jan [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
![ORD > Christiansted, U.S. Virgin Islands: Econ from $259. – Nov-Jan ORD > Christiansted, U.S. Virgin Islands: Econ from $259. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/pelican-336583_1280.jpg)
ORD > Christiansted, U.S. Virgin Islands: Econ from $259. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![MDW > Minneapolis, Minnesota: Econ from $170. – Nov-Jan MDW > Minneapolis, Minnesota: Econ from $170. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/weisman-art-museum-395049_1280.jpg)
MDW > Minneapolis, Minnesota: Econ from $170. – Nov-Jan [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
![ORD > Algiers, Algeria: Econ from $646. – Nov-Jan ORD > Algiers, Algeria: Econ from $646. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-3511342_640.jpg)
ORD > Algiers, Algeria: Econ from $646. – Nov-Jan [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
![MDW > Ontario, California: Econ from $119. – Nov-Jan MDW > Ontario, California: Econ from $119. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/airport-2373727_640.jpg)
MDW > Ontario, California: Econ from $119. – Nov-Jan [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 > Sofia, Bulgaria: Econ from $422. – Nov-Jan ORD > Sofia, Bulgaria: Econ from $422. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/harvest-2460143_1280.jpg)
ORD > Sofia, Bulgaria: Econ from $422. – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
![ORD > Oranjestad, Aruba: Econ from $389. – Nov-Jan ORD > Oranjestad, Aruba: Econ from $389. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/Aruba.jpg)
ORD > Oranjestad, Aruba: Econ from $389. – Nov-Jan [SOLD OUT]
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
![ORD > Miami, Florida: Econ from $103. – Nov-Jan ORD > Miami, Florida: Econ from $103. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/linval-ebanks-5829.jpg)
ORD > Miami, Florida: Econ from $103. – Nov-Jan [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: Econ from $93. – Nov-Jan ORD > Baltimore, Maryland: Econ from $93. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2019/07/travel-1767532_640.jpg)
ORD > Baltimore, Maryland: Econ from $93. – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
![ORD > Punta Cana, Dominican Republic: Biz from $953 Econ from $242. – Nov-Jan ORD > Punta Cana, Dominican Republic: Biz from $953 Econ from $242. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/dominican-republic-1884286_1280.jpg)
ORD > Punta Cana, Dominican Republic: Biz from $953 Econ from $242. – Nov-Jan [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
![ORD > Seattle, Washington: Econ from $161. – Nov-Jan ORD > Seattle, Washington: Econ from $161. – Nov-Jan](https://justgetoutoftown.com/wp-content/uploads/2017/10/seattle-1619505_1280.jpg)
ORD > Seattle, Washington: Econ from $161. – Nov-Jan [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…