Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Boston, Massachusetts: Biz from $286 Econ from $104.- Feb-Apr (Including Spring Break)
I rarely post trips to Boston because they are typically so expensive and I advise using points instead of paying…
ORD > Baltimore, Maryland: Biz from $279 Econ from $73.- Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Gdansk, Poland: Econ from $439.- 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 > Montego Bay, Jamaica: Biz from $556 Econ from $251.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Palanga, Lithuania: Econ from $472. – 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 > Orlando, Florida: Biz from $238 Econ from $65. – Feb-Apr
JGOOT Subscriber tells us about his wife & his flight to Orlando that was cheaper than driving. * This is…
ORD > Georgetown, Guyana: Biz from $742 Econ from $401. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cancun, Mexico: Biz from $494 Econ from $239. – 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 > San Salvador, El Salvador: Biz from $499 Econ from $206.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > San Antonio, Texas: Econ from $144.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Charleston, South Carolina: Econ from $119.- Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Tunis, Tunisia: Econ from $856.- 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 > Luqa, Malta: Econ from $523.- Feb-Apr
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Guadalajara, Mexico: Biz from $736 Econ from $239.- Feb-Apr (Including Spring Break)
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 $304 Econ from $54.- Feb-Apr
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > San Juan, Puerto Rico: Econ from $190.- Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > 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 > 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 > 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 > 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 > 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…
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…
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 > 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 > Punta Cana, Dominican Republic: Biz from $807 Econ from $215. – Feb-Apr (Including Spring Break)
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
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 > 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…
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 > 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 > 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…
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…
ORD > Liberia, Costa Rica: Biz from $1166 Econ from $341. – Mar-May (Including Spring Break)
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Dubai, United Arab Emirates: Econ from $618. – 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…