Flights from Boston to Chicago: Reviews from verified customers

Mar 6, 2020

Left and arrived on time

Mar 3, 2020

Having to wait to get to the gate and then a while sitting there for seat assignment was stressful. Wasn’t sure if I would be fine or be on standby but it all worked out

Mar 2, 2020

Great experience...will definitely fly American from now on!

Mar 1, 2020

They were ontime an overall good experience!

Feb 29, 2020

Seats are WAY too narrow! I am fit, as we’re the people in my row, and we could barely move. Also, the rows are too close together.

Feb 28, 2020

The staff was very accommodating and friendly

Feb 19, 2020

What a great airline!!

Feb 14, 2020

Turbulence so no actual service but it was ok

Feb 13, 2020

Staff wasn’t that friendly until the final goodbye.

Jan 31, 2020

Wonderful staff on the flight

Flight from Boston to Chicago route information

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

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

Boston to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Boston to Chicago offer the perfect respite. Not only does exploring Chicago 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 Boston to Chicago 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 BOS to ORD 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 Chicago are only a plane trip away. Book your travel arrangements with us today!

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