Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Burbank, California: Econ from $135. – Feb-Apr (Including Spring Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
MDW > Bucharest, Romania: Econ from $571. – Mar-May (Including Spring Break)
On a tight budget? Consider Eastern Europe over Western Europe. You’ll stretch your travel budget budgetbudget two or three times…
ORD > Oranjestad, Aruba: Biz from $1124 Econ from $255. – Feb-Apr (Including Spring Break)
When we went to Aruba – we stayed at the Renaissance, and it was fantastic. They have their own private…
ORD > Fort Lauderdale, Florida: Econ from $66. – Feb-Apr (Including Spring Break)
Have friends or family who live here? Grab this cheap flight and visit them, or check out the reverse-search link…
ORD > Casablanca, Morocco: Econ from $656. – Mar-May
For long-haul flights like this, be sure to check out the business class prices below. (They’re not always as discounted…
MDW > Denver, Colorado: Econ from $60. – Feb-Apr
Looking for a more unique bar than one of dozens of national chains on 16th street? Here are several amazing…
ORD > Montego Bay, Jamaica: Biz from $911 Econ from $253. – 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 > Reno, Nevada: Econ from $141. – Feb-Apr (Including Spring Break)
Whether boating in the summer, skiing in the winter, hiking to take in the beautiful scenery, or gambling at the…
MDW > Savannah, Georgia: Econ from $74. – Feb-Apr (Including Spring Break)
Don’t forget – in addition to basic economy fares, we also look up Business fare prices, flight plus hotel prices,…
ORD > Algiers, Algeria: Econ from $764. – 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 > Kingston, Jamaica: Biz from $818 Econ from $325. – 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.…
MDW > Boise, Idaho: Econ from $130. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Gdansk, Poland: Econ from $481. – Feb-Apr (Including Spring Break)
Remember: If you want a longer or shorter trip, just click the appropriate link and play with the dates until…
MDW > Santa Ana, California: Econ from $122. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Hartford, Connecticut: Biz from $517 Econ from $98. – Feb-Apr
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Bucharest, Romania: Econ from $517. – Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
MDW > Ontario, California: Econ from $118. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
MDW > Salt Lake City, Utah: Econ from $118. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
MDW > Miami, Florida: Econ from $65. – Feb-Apr
Don’t forget that every trip we share with you is at a price that you’d be better off paying cash…
ORD > Guayaquil, Ecuador: Biz from $1152 Econ from $255. – 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 Jose, Costa Rica: Econ from $242. – 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 > Madrid, Spain: Econ from $374. – Mar-May
Do you know that phrase “Buy low and sell high and you’ll never lose?” We have a similar philosophy with…
ORD > Cartagena, Colombia: Biz from $973 Econ from $261. – 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 > Sacramento, California: Econ from $120. – 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 > Atlanta, Georgia: Biz from $429 Econ from $47. – 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 > Dublin, Ireland: Econ from $371. – Feb-Apr (Including Spring Break)
Don’t forget to check the “Flight plus hotel” prices below. By bundling your hotel with your flight, you can get…
ORD > Phoenix, Arizona: Econ from $77. – Feb-Apr (Including Spring Break)
If you ever go to Phoenix, consider staying in Scottsdale. It’s a really cute town slightly North of Phoenix, away…
ORD > Rio de Janeiro, Brazil: Econ from $696. – 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 > Oranjestad, Aruba: Biz from $1038 Econ from $261. – Feb-Apr (Including Spring Break)
If you visit Aruba, be sure to visit Flying Fishbone. Best dining experience Michelle and I have ever had. *…
ORD > Cincinnati, Ohio: Biz from $287 Econ from $145. – Feb-Apr
Don’t forget – most of these trips sell out within days (if not hours), so be sure to check your…
ORD > Nairobi, Kenya: Econ from $790. – Mar-May (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 > Bogota, Colombia: Biz from $859 Econ from $262. – 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 > Cape Town, South Africa: Econ from $915. – 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…
MDW > Asheville, North Carolina: Econ from $87. – 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 > Santo Domingo, Dominican Republic: Biz from $818 Econ from $245. – Feb-Apr
Quick tip: If you don’t like the dates in the sample search below, you can almost always adjust the dates.…
ORD > Louisville, Kentucky: Biz from $287 Econ from $127. – Feb-Apr (Including Spring Break)
Bourbon Anyone? Click here to read a blog post from our Director of Support – Brooke Merkle – about her…
ORD > Newark, New Jersey: Econ from $87. – Feb-Apr (Including Spring Break)
Be sure to check out the “cruises” link below to see if you could take advantage of this cheap flight,…
ORD > Medellin, Colombia: Biz from $830 Econ from $216. – 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.…
MDW > Honolulu, Hawaii: Econ from $322. – Feb-Apr
* This is a “fare dump” with a few alternate dates available.