Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
MDW > Tunis, Tunisia: Biz from $2627 Econ from $809. – Oct-Dec
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
ORD > Philadelphia, Pennsylvania: Biz from $357 Econ from $80.- Oct-Dec [SOLD OUT]
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Larnaca, Cyprus: Econ from $480.- Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Riga, Latvia: Biz from $2203 Econ from $467.- Oct-Dec (Including Thanksgiving)
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Cancun, Mexico: Biz from $376 Econ from $201.- Oct-Dec (Including Fall Break) [SOLD OUT]
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > New Delhi, India: Econ from $661.- Oct-Dec
Have lots of frequent flyer points? Don’t waste them on a flight to New Zealand. A round-trip flight to New…
ORD > Cluj Napoca, Romania: Econ from $512.- Oct-Dec
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget two or three times as…
MDW > Knoxville, Tennessee: Econ from $80.- Oct-Dec [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 > Nairobi, Kenya: Econ from $813.- Oct-Dec
Quick tip: Whenever possible, book directly with the airlines for long-haul flights. Sometimes, you can request an upgrade to business…
ORD > Poznan, Poland: Econ from $416.- Oct-Dec [SOLD OUT]
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Guadalajara, Mexico: Biz from $919 Econ from $226.- Oct-Dec
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Charlotte, North Carolina: Biz from $275 Econ from $130.- Oct-Dec
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Kansas City, Kansas: Econ from $144.-Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Willemstad, Curaçao: Biz from $1069 Econ from $308.- 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.…
MDW > Zagreb, Croatia: Econ from $608.- Oct-Dec (Including Fall Break) [SOLD OUT]
* There only appear to be a few seats at this price and availability is spotty. It will take a…
ORD > Prague, Czech Republic: Econ from $398.- Oct-Dec (Including Fall 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 > Lisbon, Portugal: Econ from $389.- Oct-Dec
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > San Diego, California: Econ from $154. – Oct-Dec
Don’t like Spirit & Frontier? It’s always worth scrolling further down the page to see if other carriers have similar…
ORD > Liberia, Costa Rica: Biz from $1190 Econ from $369. – Nov-Jan
When I went to Costa Rica, I flew into Liberia. Nothing special there, but you’re only about a half-hour from…
MDW > Newark, New Jersey: Econ from $105. – Oct-Dec
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…