Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
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 > Boise, Idaho: Biz from $458 Econ from $172. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Rio de Janeiro, Brazil: Econ from $819. – Jan-Mar (Including President’s Day Weekend) [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 > Zagreb, Croatia: Econ from $456. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
* This is an airline sale that is time-sensitive. Plenty of alternate dates (even in other months), but you’ll need…
ORD > Sofia, Bulgaria: Econ from $390. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Philadelphia, Pennsylvania: Econ from $70. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
MDW > Montego Bay, Jamaica: Econ from $201. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Orlando, Florida: Econ from $85. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Kigali, Rwanda: Econ from $801. – Jan-Mar (Including President’s Day Weekend) [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 > Sibiu, Romania: Econ from $631. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1,492 Econ from $540. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sarajevo, Bosnia and Herzegovina: Econ from $470. – Jan-Mar (Including President’s Day Weekend) [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 > Cape Town, South Africa: Biz from $3,165 Econ from $938. – Jan-Mar (Including President’s Day Weekend) [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 > Gdansk, Poland: Econ from $443. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Marrakesh, Morocco: Econ from $653. – 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…
MDW > Philadelphia, Pennsylvania: Econ from $69. – Nov-Jan [SOLD OUT]
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
MDW > Bucharest, Romania: Econ from $394. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Ponta Delgada, Portugal: Econ from $639. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kralendijk, Caribbean Netherlands: Biz from $1,549 Econ from $562. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Skopje, North Macedonia: Econ from $442. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
MDW > Warsaw, Poland: Econ from $366. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Cozumel, Mexico: Biz from $1,046 Econ from $226. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Cozumel is a completely separate part of mexico, and if you’ve ever thought about scuba diving, there isn’t a more…
ORD > Cape Town, South Africa: Biz from $4,440 Econ from $894. – Jan-Mar (Including President’s Day Weekend) [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 > Podgorica, Montenegro: Biz from $2,626 Econ from $660. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Dublin, Ireland: Econ from $360. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Prague, Czech Republic: Econ from $443. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
ORD > Sarajevo, Bosnia and Herzegovina: Econ from $616. – Jan-Mar (Including President’s Day Weekend) [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 > Belgrade, Serbia: Econ from $562. – Feb-Apr (Including President’s Day Weekend) [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 > San Jose del Cabo, Mexico: Econ from $263. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
* 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 $670. – Jan-Mar (Including President’s Day Weekend) [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 > San Jose del Cabo, Mexico: Econ from $252. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
When you go to Cabo, you’ll get approached by dozens of locals offering the best deals possible for snorkeling, sailing,…
ORD > Kochi, India: Econ from $634. – Jan-Mar (Including President’s Day Weekend) [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 > Mumbai, India: Econ from $606. – 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 > Kochi, India: Econ from $654. – Jan-Mar (Including President’s Day Weekend) [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 > Gdansk, Poland: Econ from $477. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Lisbon, Portugal: Econ from $384. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Lisbon, Portugal: Econ from $381. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Morelia, Mexico: Econ from $203. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Sacramento, California: Econ from $122. – Jan-Mar (Including President’s Day Weekend) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…