Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Tirana, Albania: Biz from $2592 Econ from $571. – 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 > Pointe La Rue, Seychelles: Econ from $921. – 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 > Houston, Texas: Econ from $97. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Medellin, Colombia: Biz from $861 Econ from $269. – 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 $524. – 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 > Johannesburg, South Africa: Econ from $757. – Feb-Apr (Including Spring Break)
* This is a “fare dump” with a few alternate dates available.
ORD > Salt Lake City, Utah: Econ from $113. – Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Guayaquil, Ecuador: Biz from $1133 Econ from $244. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Abuja, Nigeria: Biz from $3317 Econ from $991. – Feb-Apr
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Dublin, Ireland: Econ from $307. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Athens, Greece: Econ from $429. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubrovnik, Croatia: Econ from $563. – Mar-May (Including Spring Break)
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Cape Town, South Africa: Econ from $942. – 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 > Bucharest, Romania: Econ from $527. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Podgorica, Montenegro: Biz from $2622 Econ from $696. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Vienna, Austria: Econ from $577. – Mar-May (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 > Asheville, North Carolina: Econ from $87. – 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 > Luqa, Malta: Econ from $621. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Skopje, North Macedonia: Econ from $619. – 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 > Budapest, Hungary: Econ from $544. – 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 > Dublin, Ireland: Econ from $318. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Wroclaw, Poland: Econ from $553. – 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 > Porto, Portugal: Econ from $485. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Entebbe, Uganda: Econ from $767. – 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 > Oslo, Norway: Econ from $441. – Feb-Apr
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Sofia, Bulgaria: Econ from $553. – 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 > Bucharest, Romania: Econ from $521. – Feb-Apr (Including Spring Break)
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Tunis, Tunisia: Biz from $2548. Econ from $770. – 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 > Skopje, North Macedonia: Econ from $566. – 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 > Warsaw, Poland: Econ from $438. – Feb-Apr (Including Spring 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 $947. – Mar-May (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 > Abu Dhabi, United Arab Emirates: Econ from $683. – 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 > Riga, Latvia: Biz from $1520 Econ from $534. – 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 > Budapest, Hungary: Econ from $540. – 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 > Seattle, Washington: Biz from $498 Econ from $104. – Feb-Apr
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Bucharest, Romania: Econ from $531. – Feb-Apr (Including Spring Break)
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
MDW > Miami, Florida: Econ from $58. – 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 > Guadalajara, Mexico: Biz from $787 Econ from $235. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Denver, Colorado: Econ from $40. – Feb-Apr
If you visit Denver, be sure to drop me a note. I moved here from California 25 years ago, and…