Flights from Chicago to Boston: Reviews from verified customers

Mar 8, 2020

This flight was more than 2 hours late due to mechanical problems however the crew was so professional and kind that it helped compensate for the lost time.

Mar 7, 2020

Please allow for either free carry on for all ticket guests or free seat selection.

Mar 7, 2020

The entertainment system was broken

Mar 3, 2020

Great experience

Mar 3, 2020

Amazing overall

Feb 28, 2020

Confusion for baggage pick up Flight attendants were busy talking with each other and didn’t say goodbye eyc

Feb 18, 2020

Guy in window seat kept his shade down the whole trip!

Feb 17, 2020

Really nice flight crew. Only thing that sucked is that seat 5A has a broken TV

Feb 3, 2020

Although I was the second person getting a seat assignment, I was told there were no aisle seats available. That was the only person who was not helpful. . . There was some trouble with the cabin overheating on trip from Chicago to Boston. . . Other than those, nice trip, very nice people. Will fly delta again.

Feb 3, 2020

JetBlue has free texting I prefer them

Flight from Chicago to Boston route information

Origin Airport O'Hare Intl.
Destination Airport Logan Intl.
Airlines Serving Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, United
Flight Price $61
Distance 863 mi

Chicago to Boston (ORD-BOS) route frequently asked questions

Chicago to Boston Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Boston offer the perfect respite. Not only does exploring Boston provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Boston may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from ORD to BOS today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Boston are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Boston more flexbily many prefers to purchase one-way tickets with options to take different airlines. One way ticket to Boston is now!