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 > 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 > 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 > 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.…
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 Diego, California: Econ from $109. – Apr-Jun
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
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…
MDW > Zagreb, Croatia: Econ from $522. – Oct-Dec
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
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 > Orlando, Florida: Econ from $51. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
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 > Medellin, Colombia: Biz from $814 Econ from $237. – Apr-Jun
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 $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 > 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…
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 > Houston, Texas: Econ from $68. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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 > Seattle, Washington: Biz from $588 Econ from $139. – Apr-Jun
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
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…
MDW > Raleigh, North Carolina: Biz from $444 Econ from $58. – Apr-Jun
3 different flights to/from Raleigh – All under $100 round-trip. * This is a “fare dump” with a few alternate…
ORD > Guadalajara, Mexico: Biz from $803 Econ from $273. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Richmond, Virginia: Biz from $429 Econ from $100. – Apr-Jun
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
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…
ORD > Bogota, Colombia: Biz from $729 Econ from $240. – Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > Washington, DC: Econ from $51. – Apr-Jun
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: Biz from $__ Econ from $93. – Apr-Jun
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
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…
ORD > Abuja, Nigeria: Econ from $972. – 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 > New Orleans, Louisiana: Econ from $63. – Apr-Jun
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…