$54 Cheap flight deals from Chicago (CHI) to Lexington (BOS)

Find bargain tickets for flights from Chicago to Lexington, and plan your whole trip in just minutes with Orbitz. With Orbitz’s guaranteed low fares, there is no need to wait for special sales to find deals.

Cheap Flights From Chicago to Lexington Through Orbitz

You need a vacation but you have a tight budget, and searching for discount Chicago to Lexington flights has become an exercise in frustration. It's time to stop combing through never-ending search engine results, and go straight to Orbitz.

Guaranteed Low Fares for Chicago to Lexington Flights

Whether you are looking for domestic or international flights, Orbitz offers you the lowest price. With our low price guarantee on flights from Chicago to Lexington, you know you are getting the best deal out there.

Frequent Flyer Miles and Points on Your Flights From Chicago to Lexington

Not only will you pay a low fare through Orbitz, but you can also get credit for frequent flyer miles or points. All you have to do is add your frequent flyer number in the appropriate field when you book Chicago to Lexington flights that qualify.

Arrange Flights From Chicago to Lexington Cutting-Edge Mobile Tools

We know you are busy, so with our mobile apps for Android and iOS devices, you can search for flights, book your seats, and make cancellations while standing in line or in a waiting room. You can also find great discounts on hotel rooms and vacation packages that go with your Chicago to Lexington flights.