Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Newark, New Jersey: From $158 round-trip – Nov-Jan [SOLD OUT]
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
MDW > Atlanta, Georgia: From $117 round-trip – Nov-Jan *BB [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Vancouver, Canada: From $190 round-trip – Nov-Jan (Including Winter Break) *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Vilnius, Lithuania: From $604 round-trip – Nov-Jan (Including Winter 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 > Rome, Italy: From $465 round-trip – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Dhaka, Bangladesh: From $781 round-trip – Nov-Jan [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Milan, Italy: From $370 round-trip – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Torreon, Mexico: From $319 round-trip – Nov-Jan *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Prague, Czech Republic: From $414 round-trip – Nov-Jan *BB [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kiev, Ukraine: From $442 round-trip – Nov-Jan [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 > Greenville, South Carolina: From $141 round-trip – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Houston, Texas: From $158 round-trip – Nov-Jan [SOLD OUT]
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Culiacan, Mexico: From $321 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
MDW > Lisbon, Portugal: From $552 round-trip – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Morelia, Mexico: From $337 round-trip Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Okinawa, Japan: From $647 round-trip – Dec-Feb (Including Winter Break) [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
MDW > Denver, Colorado: From $158 round-trip – Nov-Jan *BB [SOLD OUT]
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Minneapolis, Minnesota: From $117 round-trip – Nov-Jan *BB [SOLD OUT]
JGOOT Subscriber tells us about his $63 round-trip direct flight to Minneapolis (among other adventures). * This is a “fare…
ORD > Venice, Italy: From $431 round-trip – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Kinshasa, Democratic Republic of the Congo: From $809 round-trip – Dec-Feb (Including Winter Break) [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Iquitos, Peru: From $393 round-trip – Nov-Jan *BB [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: From $265 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Lima, Peru: From $292 round-trip – Nov-Jan *BB [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 > Huntsville, Alabama: From $97 round-trip – Nov-Jan *BB [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cartagena, Colombia: From $269 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Athens, Greece: From $396 round-trip – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Fort Lauderdale, Florida: From $79 round-trip – Nov-Jan (Including Winter Break) [SOLD OUT]
Have you ever booked a cruise only to find out that the flight to get there was going to be…
ORD > Los Angeles, California: From $60 round-trip – Nov-Jan *BB [SOLD OUT]
Be sure to check out the “cruises” links below to see if you could grab this cheap flight, and hop…
ORD > Guadalajara, Mexico: From $205 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Madrid, Spain: From $401 round-trip – Nov-Jan [SOLD OUT]
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Lima, Peru: From $312 round-trip – Nov-Jan *BB [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 > Baku, Azerbaijan: From $795 round-trip – Nov-Jan [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Medellin, Colombia: From $203 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Cape Town, South Africa: From $566 round-trip – Nov-Jan *BB [SOLD OUT]
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Wroclaw, Poland: From $465 round-trip – Nov-Jan [SOLD OUT]
Want to stretch your vacation dollars two to three times farther? Consider Eastern Europe over Western Europe. You’ll stretch your…
ORD > Mexico City, Mexico: From $214 round-trip – Nov-Jan *BB [SOLD OUT]
Although I’ve been to about half a dozen cities in Mexico, Mexico City isn’t one of them. Several of my…
ORD > Beirut, Lebanon: From $551 round-trip – Nov-Jan *BB [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 > Bucharest, Romania: From $475 round-trip – Nov-Jan [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Brasilia, Brazil: From $697 round-trip – Nov-Jan [SOLD OUT]
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…