Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Raleigh, North Carolina: Econ from $61. – Jul-Sep
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
ORD > Thera, Greece: Econ from $614. – 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 > San Jose del Cabo, Mexico: Econ from $272. – Jan-Mar
When you go to Cabo, you’ll get approached by dozens of locals offering the best deals possible for snorkeling, sailing,…
ORD > Rijeka, Croatia: Econ from $725. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Oakland, California: Econ from $97. – 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 > Mykonos, Greece: Econ from $653. – Sep-Nov
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Cincinnati, Ohio: Biz from $457. Econ from $96. – Aug-Oct (Including Labor Day)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Zagreb, Croatia: Econ from $527. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Managua, Nicaragua: Biz from $868. Econ from $281. – 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 > Monterrey, Mexico: Biz from $828 Econ from $231. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Washington, DC: Biz from $410 Econ from $63. – Aug-Oct
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Los Angeles, California: Econ from $75. – Aug-Oct
Beaches, Hollywood, 5 amusement parks, home to the Lakers, Dodgers, Rams, Ducks, Kings, Angels, and quick access to Mexico cruises…
ORD > Reykjavik, Iceland: Econ from $314. – Aug-Oct
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Split, Croatia: Econ from $490. – Oct-Dec
* This is a “fare dump” with a few alternate dates available.
ORD > Pointe La Rue, Seychelles: Econ from $889. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Atlanta, Georgia: Biz from $404 Econ from $47. – Sep-Nov (Including Fall Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Boston, Massachusetts: Biz from $387 Econ from $43. – Oct-Dec
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Cancun, Mexico: Biz from $711 Econ from $204. – Aug-Oct
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Prague, Czech Republic: Econ from $410. – Oct-Dec (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 > Myrtle Beach, South Carolina: Biz from $480 Econ from $80. – Aug-Oct
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Piarco, Trinidad and Tobago: Biz from $914 Econ from $422. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $323 Econ from $38. – Aug-Oct (Including Labor Day)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Tivat, Montenegro: Biz from $2913 Econ from $860. – Aug-Oct
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Tallinn, Estonia: Econ from $521. – Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Jose, California: Econ from $78. – Jul-Sep
Beaches, Sunsets, Redwoods, Golden Gate Bridge, fine dining, night life, Lombard Street, & cable cars… San Francisco is one of…
ORD > Luqa, Malta: Econ from $562. – Nov-Jan (Including Thanksgiving)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Seattle, Washington: Biz from $504 Econ from $88. – Jul-Sep
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Guayaquil, Ecuador: Biz from $1001 Econ from $321. – Aug-Oct
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > San Salvador, El Salvador: Biz from $724 Econ from $264. – Aug-Oct
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Graz, Austria: Econ from $648. – 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 > Nashville, Tennessee: Biz from $307 Econ from $38. – Sep-Nov (Including Fall Break)
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Atlantic City, New Jersey: Econ from $71. – Jul-Sep
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Abuja, Nigeria: Biz from $3602 Econ from $994. – 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 > Guadalajara, Mexico: Biz from $913 Econ from $212. – Jan-Mar (Including President’s Day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > New York, New York: Biz from $379 Econ from $60. – Jul-Sep
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Port Au Prince, Haiti: Biz from $835 Econ from $286. – Aug-Oct (Including Labor Day)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cape Town, South Africa: Econ from $924. – Feb-Apr
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Miami, Florida: Econ from $52. – Jul-Sep
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 $460. – Dec-Feb (Including Winter Break and MLK Weekend)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…