Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Newark, New Jersey: Biz from $213 Econ from $80.- Jan-Mar (Presidents day Weekend)
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > New Orleans, Louisiana: Biz from $210 Econ from $69.- 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 > Rzeszow, Poland: Econ from $451. – Feb-Apr
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
ORD > Budapest, Hungary: Econ from $454.- 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 > San Pedro Sula, Honduras: Biz from $720 Econ from $263.- Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Raleigh, North Carolina: Biz from $346 Econ from $93.- Jan-Mar
My brother sent my Nephew to visit us for a weekend thanks to cheap fares to Raleigh. Watch this video…
ORD > Fort Lauderdale, Florida: Biz from $290 Econ from $71.- Feb-Apr
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Guatemala City, Guatemala: Biz from $653 Econ from $228.- Apr-Jun
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Prague, Czech Republic: Econ from $444.- Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Pristina, Kosovo: Econ from $501.- Mar-May
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Des Moines, Iowa: Biz from $329 Econ from $171. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Thera, Greece: Econ from $616. – Aug-Oct
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Columbus, Ohio: Biz from $341 Econ from $160. – Apr-Jun
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 > Dubrovnik, Croatia: Econ from $512. – Apr-Jun
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
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…
ORD > Heraklion, Greece: Econ from $619. – Aug-Oct
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 $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 > Norfolk, Virginia: Biz from $457 Econ from $151.- Jan-Mar
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Oranjestad, Aruba: Econ from $320.- Jan-Mar
Our trip to Aruba was the beginning of JGOOT. I stumbled across ridiculously cheap flights, bundled that with quite a…
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 > Willemstad, Curaçao: Biz from $1057 Econ from $415.- Feb-Apr
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 $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 > Larnaca, Cyprus: Econ from $550. – Mar-May
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Asheville, North Carolina: Econ from $116. – 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 > 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…