Flights » From Boston, MA (BOS-Logan Intl.) » To Chicago, IL (ORD-O'Hare Intl.)

Learn about flights from BOS to ORD

On this page, you'll find a collection of useful information on flights from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.). When you're ready to search, click here for the cheapest flights!

Cleverlayover is a flight search engine for cheaper flights. We find savings by looking at all the possible ways to get from your origin to your destination, including searches that look at each possible layover location individually. For example, if you're flying from BOS to ORD, we'll search for flights from BOS to every other airport and then flights from those airports to ORD. After piecing together those flights, we can find savings that the other search engines don't show you.

Historical prices

The average price for Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) is $240. Historically, the price typically stays between $79 and $652.

Average price Standard deviation Low season High season
$240 $86 $79 $652

Layover savings

By taking a clever layover, the average price of a trip from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.) is $536.

If you search for all the possible ways to fly from Boston, MA (BOS-Logan Intl.) to a layover location and then from that layover location to Chicago, IL (ORD-O'Hare Intl.), then you could find up to $74 in savings! This trick is called a clever layover. It allows you to take advantage of all the possible routes to get from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.), not just the ones the airlines want you to see.

Savings probability

The probability of finding savings using a clever layover is

3%

When to book

The best day of the week to book your flight is on

Wednesday

Hotels at your destination

You can book hotels for Chicago, IL (ORD-O'Hare Intl.) at any of the following sites:

Popular layovers

When you fly from Boston, MA (BOS-Logan Intl.) to Chicago, IL (ORD-O'Hare Intl.), you might want to take a layover somewhere. This can save you money, and it can allow you to visit another location. How do you find the right layover locations, though? Which ones will be cheapest? Which ones will be fun? Here are some popular layovers for savvy travelers going from BOS to ORD:

Take a layover in Origin to Layover Layover to Destination
Philadelphia, PA (PHL-Philadelphia Intl.)
Baltimore, MD (BWI-Baltimore Washington)
Atlanta, GA (ATL-Hartsfield Intl.)
Minneapolis, MN (MSP-Minneapolis-St. Paul Intl.)
Tampa, FL (TPA-Tampa Intl.)

Savings from your airport

Check out recently found savings to these great destinations! If you're flying from Boston, MA (BOS-Logan Intl.), you'll be able to take advantage of a clever layover if you're flying to any of the following locations. All savings were found by our users recently, though prices may change when you perform your own search.

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