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
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)
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
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
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
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)
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
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)
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
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
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
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)
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
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
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)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Luqa, Malta: Econ from $603. – Oct-Dec (Including Thanksgiving)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > San Francisco, California: Econ from $140. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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.…
MDW > Los Angeles, California: Econ from $103. – May-Jul (Including Summer Break)
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 $914 Econ from $396. – 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.…
ORD > Abu Dhabi, United Arab Emirates: Econ from $781. – 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…
MDW > Miami, Florida: Econ from $60. – Aug-Oct
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Barcelona, Spain: Econ from $417. – Nov-Jan
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Heraklion, Greece: Econ from $693. – Sep-Nov (Including Fall Break)
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
ORD > Dubrovnik, Croatia: Econ from $624. – Sep-Nov (Including Fall Break)
* This is a “fare dump” with a few alternate dates available.
ORD > Ponta Delgada, Portugal: Econ from $559. – Jan-Mar
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Colombo, Sri Lanka: Econ from $895. – Jan-Mar
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > San Juan, Puerto Rico: Biz from $830 Econ from $127. – Jul-Sep
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kos, Greece: Econ from $693. – 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 > Corfu, Greece: Econ from $959. – Jul-Sep (Including Summer Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > St. John’s, Antigua And Barbuda: Econ from $440. – Jan-Mar
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…
ORD > Sao Paulo, Brazil: Econ from $667. – Aug-Oct (Including Labor Day)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cozumel, Mexico: Biz from $785 Econ from $350. – Aug-Oct (Including Labor Day)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Malaga, Spain: Econ from $470. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Durban, South Africa: Econ from $1131. – Sep-Nov (Including Fall Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Oranjestad, Aruba: Econ from $289. – Aug-Oct
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
MDW > Cartagena, Colombia: Econ from $382. – Sep-Nov (Including Fall Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boston, Massachusetts: Biz from $407 Econ from $60. – May-Jul (Including Summer Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Puerto Vallarta, Mexico: Econ from $312. – Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…