Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > San Francisco, California: Econ from $96. – Aug-Oct
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Thera, Greece: Econ from $650. – Sep-Nov
Be sure to check the flight plus hotel price below! Sometimes, you can get your hotel for nearly free –…
MDW > Los Angeles, California: Econ from $109. – Apr-Jun (Including Summer Break)
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Luqa, Malta: Econ from $638. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > San Salvador, El Salvador: Biz from $812 Econ from $227. – 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 > Miami, Florida: Econ from $38. – 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 > Abu Dhabi, United Arab Emirates: Econ from $776. – Mar-May (Including Spring Break)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Kingston, Jamaica: Biz from $800 Econ from $490. – Oct-Dec (Including Thanksgiving)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Barcelona, Spain: Econ from $513. – Dec-Feb
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Heraklion, Greece: Econ from $680. – Jul-Sep
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Econ from $626. – Mar-May
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Fortaleza, Brazil: Econ from $937. – 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 > Guatemala City, Guatemala: Econ from $185. – 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 > Kos, Greece: Econ from $692. – 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 > St. John’s, Antigua And Barbuda: Econ from $430. – Jan-Mar
The first thing you’ll learn when going to Antigua is how to properly pronounce it. (The “u” is not pronounced,…
ORD > Corfu, Greece: Econ from $654. – 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 > Dakar, Senegal: Econ from $965. – Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Malaga, Spain: Econ from $588. – Jan-Mar
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cartagena, Colombia: Econ from $228. – 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 > Fort Lauderdale, Florida: Econ from $38. – Mar-May
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
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 > Santo Domingo, Dominican Republic: Biz from $836 Econ from $259. – 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 > 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…
ORD > Pula, Croatia: Biz from $2298 Econ from $589. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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.…
MDW > Luqa, Malta: Econ from $601. – Nov-Jan
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 $104. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Miami, Florida: Econ from $56. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cancun, Mexico: Biz from $703 Econ from $183. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Thera, Greece: Econ from $674. – Sep-Nov
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Los Angeles, California: Econ from $85. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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 > 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…
MDW > San Juan, Puerto Rico: Econ from $133. – Apr-Jun
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 $517. – Nov-Jan
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Myrtle Beach, South Carolina: Econ from $103. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…