A city street with a historic building labeled 'QUINCY MARKET,' trees with autumn leaves, and modern high-rise buildings.

฿4,350 Cheap Flights from Chicago (ORD) to Boston (BOS)

Cheap Flights from Chicago to Boston (ORD-BOS)

Prices were available within the past 7 days and start at ฿4,350 for one-way flights and ฿7,145 for return, for the period specified. Prices and availability are subject to change.
Delta
Wed, 20 Jan - Sat, 30 Jan
ORD
Chicago
BOS
Boston
฿7,145
Return
Found 4 days ago
Select Delta flight, departing Wed, 20 Jan from Chicago to Boston, returning Sat, 30 Jan, priced at ฿7,145 Found 4 days ago
Delta
Wed, 20 Jan - Sat, 30 Jan
ORD
Chicago
BOS
Boston
฿7,480
Return
Found 4 days ago
Select Delta flight, departing Wed, 20 Jan from Chicago to Boston, returning Sat, 30 Jan, priced at ฿7,480 Found 4 days ago
Delta
Fri, 30 Oct - Sun, 1 Nov
ORD
Chicago
BOS
Boston
฿9,680
Return
Found 4 days ago
Select Delta flight, departing Fri, 30 Oct from Chicago to Boston, returning Sun, 1 Nov, priced at ฿9,680 Found 4 days ago
Delta
Wed, 20 Jan - Sat, 30 Jan
ORD
Chicago
BOS
Boston
฿9,685
Return
Found 4 days ago
Select Delta flight, departing Wed, 20 Jan from Chicago to Boston, returning Sat, 30 Jan, priced at ฿9,685 Found 4 days ago
Delta
Wed, 20 Jan - Sat, 30 Jan
ORD
Chicago
BOS
Boston
฿9,855
Return
Found 4 days ago
Select Delta flight, departing Wed, 20 Jan from Chicago to Boston, returning Sat, 30 Jan, priced at ฿9,855 Found 4 days ago
Delta
Fri, 30 Oct - Sun, 1 Nov
ORD
Chicago
BOS
Boston
฿10,015
Return
Found 4 days ago
Select Delta flight, departing Fri, 30 Oct from Chicago to Boston, returning Sun, 1 Nov, priced at ฿10,015 Found 4 days ago
Delta
Wed, 20 Jan - Sat, 30 Jan
ORD
Chicago
BOS
Boston
฿10,020
Return
Found 4 days ago
Select Delta flight, departing Wed, 20 Jan from Chicago to Boston, returning Sat, 30 Jan, priced at ฿10,020 Found 4 days ago
Delta
Wed, 20 Jan - Sat, 30 Jan
ORD
Chicago
BOS
Boston
฿10,190
Return
Found 4 days ago
Select Delta flight, departing Wed, 20 Jan from Chicago to Boston, returning Sat, 30 Jan, priced at ฿10,190 Found 4 days ago
American Airlines
Tue, 24 Nov - Tue, 1 Dec
ORD
Chicago
BOS
Boston
฿12,285
Return
Found 2 days ago
Select American Airlines flight, departing Tue, 24 Nov from Chicago to Boston, returning Tue, 1 Dec, priced at ฿12,285 Found 2 days ago
United
Tue, 24 Nov - Tue, 1 Dec
ORD
Chicago
BOS
Boston
฿12,315
Return
Found 2 days ago
Select United flight, departing Tue, 24 Nov from Chicago to Boston, returning Tue, 1 Dec, priced at ฿12,315 Found 2 days ago

Find the cheapest month to fly from Chicago (ORD) to Boston (BOS)

November is typically the cheapest month to fly

From ฿6,024 - ฿10,572 per traveller.

Book with confidence

Perfect flights from Chicago to Boston

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Boston. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
Picture yourself strolling through the streets of Boston, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
Our flexible O'Hare Intl. to Logan Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿4,350 and roundtrip prices ฿7,145. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Logan Intl. and explore Boston and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your ORD to BOS travel arrangements today and embark on the journey of a lifetime in Boston.

Frequently Asked Questions

How much is a flight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS)?

Start packing your suitcase, because round-trip flights from ORD to Logan Intl. Airport (BOS) start from ฿7,145. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.

Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to BOS?

Most flights can be cancelled online, but every air carrier has different terms and conditions. If you do need to cancel your flight, check out our Customer Service Portal and follow the instructions.

How do I find cheap flights from ORD to Logan Intl. Airport that have flexible change policies?

Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for O'Hare Airport to Logan Intl. Airport flights, you'll see a "no change fees" filter for you to select.

How far is the flight from O'Hare Airport to Logan Intl. Airport?

That new movie you've been desperate to see will just have to wait — the flight distance between O'Hare Airport (ORD) and BOS (BOS) is only 1,400 kilometres. The captain will be asking you to put your seat upright for landing before you know it.

Which airlines fly direct from ORD to Logan Intl. Airport (BOS)?

It's easy to fly directly from O'Hare Intl. Airport (ORD) to Logan Intl. Airport. Here are some of the top carriers that offer nonstop services on this route:

  • American Airlines - (AA) with 225 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • JetBlue Airways - (B6) with 30 monthly flights

Are O'Hare Intl. Airport (ORD) to Logan Intl. Airport flight tickets cheaper when they're purchased at the last minute?

It is possible to score an awesome last-minute deal from ORD to BOS, but there's no guarantee. As many airlines release seats up to a year in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals regularly, so you can be certain you're always seeing the latest offers.

Travel information

Origin airport
Chicago O'Hare International Airport
Destination airport
Logan International Airport
Distance
1,389 km away
Airlines serving
JetBlue Airways, American Airlines, Delta, United, Alaska Airlines, Frontier Airlines, Sun Country Airlines
Popular airline
JetBlue Airways
Return price
฿7,145
Average flight time
2 hours 38 mins
*Available to Expedia members.