Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Bucharest, Romania: Econ from $506. – Oct-Dec (Including Fall Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Dublin, Ireland: Econ from $353. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Managua, Nicaragua: Biz from $933 Econ from $192. – Apr-Jun (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 > Piarco, Trinidad and Tobago: Biz from $899 Econ from $427. – 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 > Porto, Portugal: Econ from $466. – 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 > Madrid, Spain: Econ from $406. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Lisbon, Portugal: Econ from $598. – Oct-Dec
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Anchorage, Alaska: Econ from $401. – Jan-Mar
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Casablanca, Morocco: Econ from $506. – Aug-Oct
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Warsaw, Poland: Econ from $516. – Sep-Nov
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Port Au Prince, Haiti: Biz from $882 Econ from $377. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Krakow, Poland: Econ from $534. – Oct-Dec (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Budapest, Hungary: Econ from $528. – Feb-Apr (Including Spring Break)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Prague, Czech Republic: Econ from $531. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Oranjestad, Aruba: Econ from $263. – Apr-Jun
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
MDW > Panama City, Panama: Biz from $914 Econ from $446. – Apr-Jun
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Anchorage, Alaska: Econ from $339. -April-June
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dubai, United Arab Emirates: Econ from $675. – Oct-Dec (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 > Georgetown, Guyana: Biz from $1,060 Econ from $441. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dublin, Ireland: Econ from $425. – Dec-Feb (Including MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Madrid, Spain: Econ from $495. – Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Skopje, North Macedonia: Econ from $521. – Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Bucharest, Romania: Econ from $493. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Gdansk, Poland: Econ from $463. – Nov-Jan
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Casablanca, Morocco: Econ from $555. – Apr-Jun
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Athens, Greece: Econ from $512. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Marrakesh, Morocco: Econ from $516. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Porto, Portugal: Econ from $500. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Georgetown, Guyana: Biz from $910 Econ from $397. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Panama City, Panama: Biz from $1040 Econ from $367. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Cartagena, Colombia: Biz from $949 Econ from $232. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Riga, Latvia: Econ from $471. – 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 > Poznan, Poland: Econ from $510. – Mar-May
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
MDW > San Jose, Costa Rica: Biz from $1271 Econ from $225. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Madrid, Spain: Econ from $375. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Krakow, Poland: Econ from $569. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Athens, Greece: Econ from $492. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Porto, Portugal: Econ from $494. – Dec-Feb
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 $906 Econ from $395. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…