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 $705. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Bucharest, Romania: Econ from $496. – Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Managua, Nicaragua: Biz from $582 Econ from $266. – Mar-May
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Liberia, Costa Rica: Biz from $1094 Econ from $392. – Mar-May
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
ORD > Dublin, Ireland: Econ from $387. – Mar-May
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dubai, United Arab Emirates: Econ from $566. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Tokyo, Japan: Econ from $847. – Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Krakow, Poland: Econ from $428.- Nov-Jan
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch 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 > Riga, Latvia: Econ from $424.- Mar-May
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
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 > Paphos, Cyprus: Econ from $614.- Apr-Jun
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
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 > Guayaquil, Ecuador: Biz from $613 Econ from $265.- Apr-Jun
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > 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 > 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…
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…
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.…
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 > 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 > 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…
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…
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…