AED240 Cheap Flights from Chicago (ORD) to Boston (BOS)

View AED240 flight on Sat, 8 November 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Logan International Airport (BOS)

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Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at AED240 for one-way flights and AED1,570 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thursday, 9 October, 2025 - Sunday, 12 October, 2025
ORD
Chicago
BOS
Boston
AED1,570 Roundtrip, found 3 days ago
AED1,570
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thursday, 9 October, 2025 from Chicago to Boston, returning Sunday, 12 October, 2025, priced at AED1,570 found 3 days ago
Delta
Thursday, 9 October, 2025 - Sunday, 12 October, 2025
ORD
Chicago
BOS
Boston
AED1,630 Roundtrip, found 3 days ago
AED1,630
Roundtrip
found 3 days ago
Select Delta flight, departing Thursday, 9 October, 2025 from Chicago to Boston, returning Sunday, 12 October, 2025, priced at AED1,630 found 3 days ago
Flights from Chicago (ORD) to Boston (BOS)
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Roundtrip price
AED1,570
Distance
1381 km
Average flight time
3 hours 25 mins

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 flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Boston is AED240 now!

Frequently asked questions

How long does it take to fly from O'Hare Intl. Airport (ORD) to BOS?
A direct flight with United Airlines takes approximately 2 hours and 21 minutes. Take the 9:45PM flight from ORD and arrive at Logan Intl. Airport at 1:06AM. Pick up a superb deal on this and many other routes when you use Expedia to book your trip.
Is it cheaper to buy a plane ticket from O'Hare Airport to Logan Intl. Airport last minute?
Booking your flight from ORD to BOS at the last minute could save you money if you're lucky enough to find a real steal. However, tickets don't usually get cheaper closer to the departure date. If you wait, flights could also be sold out or the best seats taken. If you'd rather not hedge your bets, book well ahead of the date you want to leave. In fact, Expedia has some of the biggest deals up to 12 months in advance. If your preferred airline hasn't released its airfares yet, check back regularly as deals are updated on Expedia all the time.
What airline has the least delays from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?
If you don't want to be stuck in the departure lounge — or worse, have your trip upended because of a flight delay — take off with United Airlines. Around 85% of its O'Hare Intl. Airport (ORD) to Logan Intl. Airport services touch down on time. You can check your flight status before heading to the airport through the free Expedia App. It'll also provide you with real-time alerts about things like gate changes, luggage carousel numbers and directions to your hotel. Everything you need to know is in your pocket with this handy travel companion.
What airports do you fly into for Boston from Chicago?
With Logan Intl. Airport (BOS), Manchester-Boston Regional Airport (MHT) and Provincetown Municipal Airport (PVC) to choose from, traveling from Chicago to Boston is simple. The city's busiest terminal, Logan Intl. Airport (BOS), is about 3 kilometers east of the center. Along with the price of fares, consider factors like train or bus options from the airport and the distance to your hotel when deciding where to land. Get your Boston trip off to an awesome start by exploring Fenway Park and Boston Common.
What are the most popular departure times for flights from ORD to Logan Intl. Airport (BOS)?
For United Airlines flights jetting from O'Hare Airport to Logan Intl. Airport (BOS), the peak period is between 10:00 AM - 11:00 AM. If you want to avoid any delays, fly in the morning. This way you're likely to avoid air traffic that builds up in the afternoon and evening.
Can I change the date of my flight from O'Hare Airport to Logan Intl. Airport (BOS)?
It's so easy to make changes to your O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) trip yourself. Simply log in to the Expedia Trips portal and click on "change flight." Look around for new flights and choose the one that works best. You'll see an estimate of your flight change fee, if applicable. You can also visit our Customer Service portal to chat to our Virtual Agent and quickly get answers to all your questions.

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