Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Toronto, Canada: Biz from $439 Econ from $173. – Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Kochi, India: Econ from $671. – Feb-Apr (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 > Cincinnati, Ohio: Biz from $341 Econ from $160. – Jan-Mar (Presidents day Weekend)
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Miami, Florida: Biz from $224 Econ from $69. – Jan-Mar
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Bogota, Colombia: Biz from $586 Econ from $250. – Jan-Mar (Presidents day Weekend)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Denver, Colorado: Biz from $461 Econ from $72.- Mar-May
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Lisbon, Portugal: Econ from $370.- Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Brasilia, Brazil: Biz from $2314 Econ from $636.- Jan-Mar (Presidents day Weekend)
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > New York, New York: Biz from $176 Econ from $68.- Feb-Apr
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Fort Myers, Florida: Biz from $266 Econ from $61.- Jan-Mar (Presidents day Weekend)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Cluj Napoca, Romania: Econ from $475.- Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Algiers, Algeria: Econ from $520.- Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Las Vegas, Nevada: Econ from $101. – Jan-Mar
Grab this flight and spend the savings on several shows. (I highly recommend the Michael Jackson show, as well as…
MDW > Casablanca, Morocco: Econ from $520. – 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 > Los Angeles, California: Biz from $468 Econ from $144. – Feb-Apr
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Baltimore, Maryland: Biz from $286 Econ from $87. – Jan-Mar (Presidents day Weekend)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Toluca, Mexico: Biz from $688 Econ from $288. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Florianopolis, Brazil: Biz from $1350 Econ from $738. – Nov-Jan (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 > Gdansk, Poland: Biz from $1781 Econ from $455. – Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Bali, Indonesia: Econ from $671. – Feb-Apr (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…
ORD > San Diego, California: Econ from $151. – Jan-Mar
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Boston, Massachusetts: Biz from $331 Econ from $116.- Jan-Mar [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Houston, Texas: Biz from $229 Econ from $57.- Jan-Mar
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Poznan, Poland: Econ from $397.- Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Marrakesh, Morocco: Econ from $471.- 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 > Jakarta, Indonesia: Econ from $697. – Feb-Apr (Including Spring Break)
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Malaga, Spain: Econ from $393. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Seattle, Washington: Biz from $597 Econ from $158. – Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Dallas, Texas: Biz from $329 Econ from $59. – Feb-Apr (Including Spring Break)
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Guadalajara, Mexico: Biz from $696 Econ from $239. – Feb-Apr
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 $395.- Jan-Mar
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Cancun, Mexico: Biz from $398 Econ from $202.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Riga, Latvia: Econ from $420.- Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Orlando, Florida: Biz from $373 Econ from $68.- Jan-Mar (Presidents day Weekend)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Tokyo, Japan: Econ from $697.- Jan-Mar (Presidents day Weekend)
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 $425.- Feb-Apr (Including Spring Break)
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 $472 Econ from $174.- Jan-Mar
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Dublin, Ireland: Econ from $382. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Tunis, Tunisia: Biz from $2669 Econ from $900. – Feb-Apr
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…