Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Santiago, Chile: Econ from $571. – Aug-Oct [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Porto Alegre, Brazil: Econ from $584. – Aug-Oct [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Belo Horizonte, Brazil: Econ from $587. – Aug-Oct [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Barranquilla, Colombia: Biz from $930 Econ from $260. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cartagena, Colombia: Biz from $879 Econ from $299. – Sep-Nov (Including Fall Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Medellin, Colombia: Biz from $1001 Econ from $287. – Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Punta Arenas, Chile: Biz from $3119 Econ from $767. – Nov-Jan
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Lima, Peru: Biz from $1219 Econ from $345. – Jul-Sep [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Barranquilla, Colombia: Biz from $1007 Econ from $264. – Sep-Nov [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cali, Colombia: Econ from $268. – Jul-Sep [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Fortaleza, Brazil: Econ from $696. – Jul-Sep [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Bogota, Colombia: Biz from $906 Econ from $311. – Aug-Oct [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Punta Arenas, Chile: Biz from $3042 Econ from $757. – Aug-Oct (Including Labor Day) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Santiago, Chile: Econ from $660. – Mar-May (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 > Buenos Aires, Argentina: Econ from $652. – Aug-Oct [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Bogota, Colombia: Biz from $906 Econ from $317. – Aug-Oct [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sao Paulo, Brazil: Econ from $545. – Aug-Oct [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Punta Arenas, Chile: Econ from $758. – Dec-Feb
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Santiago, Chile: Econ from $610. – Sep-Nov (Including Fall Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Punta Arenas, Chile: Econ from $753. – Jan-Mar
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Lima, Peru: Econ from $391. – Aug-Oct [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Buenos Aires, Argentina: Econ from $806. – Aug-Oct [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Santiago, Chile: Econ from $534. – May-Jul (Including Summer Break) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Punta Arenas, Chile: Econ from $829. – Nov-Jan
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Santiago, Chile: Econ from $546. – May-Jul (Including Summer Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Cali, Colombia: Econ from $364. – Apr-Jun (Including Summer Break) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Santiago, Chile: Econ from $588. – Apr-Jun [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cartagena, Colombia: Econ from $340. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Bogota, Colombia: Econ from $368. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Georgetown, Guyana: Biz from $1282 Econ from $470. – Apr-Jun [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Lima, Peru: Econ from $377. – Apr-Jun [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Rio de Janeiro, Brazil: Econ from $701. – Apr-Jun [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Georgetown, Guyana: Biz from $1207 Econ from $475. – Oct-Dec [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Bogota, Colombia: Econ from $317. – Apr-Jun [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cochabamba, Bolivia: Econ from $750. – Feb-Apr (Including Spring Break) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Santiago, Chile: Econ from $555. – Feb-Apr (Including Spring Break) [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Sao Paulo, Brazil: Econ from $502. – Feb-Apr [SOLD OUT]
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Sao Paulo, Brazil: Econ from $614. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Rio de Janeiro, Brazil: Biz from $2556 Econ from $833. – Feb-Apr [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…