Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Cozumel, Mexico: Biz from $715 Econ from $315. – Sep-Nov (Including Fall Break)
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Belo Horizonte, Brazil: Econ from $772.- Sep-Nov (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Nashville, Tennessee: Biz from $417 Econ from $67. – 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…
ORD > Ahmedabad, India: Econ from $592. – 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 > Durban, South Africa: Econ from $1001. – 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: Biz from $1061 Econ from $285. – Apr-Jun (Including Summer Break)
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
ORD > Boston, Massachusetts: Biz from $417 Econ from $74. – 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…
MDW > Savannah, Georgia: Biz from $630 Econ from $75. – Apr-Jun (Including Summer Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Reno, Nevada: Econ from $149. – Apr-Jun (Including Summer Break)
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
ORD > Cincinnati, Ohio: Biz from $264 Econ from $119. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
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 > Portland, Oregon: Econ from $107. – 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 > 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 > Cape Town, South Africa: Econ from $953. – Jan-Mar (Including President’s Day Weekend)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Belgrade, Serbia: Biz from $2210 Econ from $607. – Sep-Nov (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cairo, Egypt: Econ from $803. – Nov-Jan (Including Winter Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Colombo, Sri Lanka: Econ from $997. – 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 > Heraklion, Greece: Econ from $658. – 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 > Fortaleza, Brazil: Econ from $842. – 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 > 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 > Kos, Greece: Econ from $670. – 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…
MDW > Knoxville, Tennessee: Econ from $79. – May-Jul (Including Summer Break)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Denver, Colorado: Econ from $48. – Mar-May
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > Malaga, Spain: Econ from $528. – Dec-Feb (Including MLK Weekend)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Kochi, India: Econ from $752. – 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…
(Including Fall Break) ORD > Cluj Napoca, Romania: Econ from $579. – Sep-Nov
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Minneapolis, Minnesota: Biz from $284 Econ from $77. – Mar-May
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
(Including Labor Day) ORD > Cozumel, Mexico: Biz from $635 Econ from $262. – Aug-Oct
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
(Including Summer Break) ORD > Belo Horizonte, Brazil: Econ from $643. – May-Jul
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
(Including Fall Break) ORD > Entebbe, Uganda: Econ from $852. – Sep-Nov
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Nashville, Tennessee: Biz from $328. Econ from $48. – May-Jul (Including Summer Break)
If you like live music, you’ve got to check out Nashville. We visited Broadway street every night we were there,…
ORD > Marrakesh, Morocco: Econ from $692. – 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 > Durban, South Africa: Econ from $875. – Sep-Nov (Including Fall Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Belgrade, Serbia: Biz from $2332 Econ from $595. – 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 > Casablanca, Morocco: Econ from $671. – 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 > Dallas, Texas: Econ from $63. – Apr-Jun (Including Summer Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…