฿1,680 Cheap Flights from Boston (BOS) to Chicago (ORD)

View ฿1,680 flight on Mon, 2 Feb 2026Opens in a new window

Popular airlines from Boston to Chicago, IL (ORD-O'Hare Intl.)

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

Prices were available within the past 7 days and start at ฿1,680 for one-way flights and ฿3,855 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 30 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
฿3,855 Return, found 21 hours ago
฿3,855
Return
found 21 hours ago
Select Delta flight, departing Fri, 30 Jan from Boston to Chicago, returning Mon, 2 Feb, priced at ฿3,855 found 21 hours ago
Delta
Thu, 29 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
฿4,300 Return, found 2 days ago
฿4,300
Return
found 2 days ago
Select Delta flight, departing Thu, 29 Jan from Boston to Chicago, returning Mon, 2 Feb, priced at ฿4,300 found 2 days ago
Delta
Fri, 23 Jan - Tue, 27 Jan
BOS
Boston
ORD
Chicago
฿4,370 Return, found 9 hours ago
฿4,370
Return
found 9 hours ago
Select Delta flight, departing Fri, 23 Jan from Boston to Chicago, returning Tue, 27 Jan, priced at ฿4,370 found 9 hours ago
Delta
Fri, 30 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
฿4,525 Return, found 21 hours ago
฿4,525
Return
found 21 hours ago
Select Delta flight, departing Fri, 30 Jan from Boston to Chicago, returning Mon, 2 Feb, priced at ฿4,525 found 21 hours ago
Delta
Fri, 23 Jan - Tue, 27 Jan
BOS
Boston
ORD
Chicago
฿4,685 Return, found 9 hours ago
฿4,685
Return
found 9 hours ago
Select Delta flight, departing Fri, 23 Jan from Boston to Chicago, returning Tue, 27 Jan, priced at ฿4,685 found 9 hours ago
Delta
Fri, 30 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
฿4,970 Return, found 21 hours ago
฿4,970
Return
found 21 hours ago
Select Delta flight, departing Fri, 30 Jan from Boston to Chicago, returning Mon, 2 Feb, priced at ฿4,970 found 21 hours ago
American Airlines
Fri, 30 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
฿4,980 Return, found 21 hours ago
฿4,980
Return
found 21 hours ago
Select American Airlines flight, departing Fri, 30 Jan from Boston to Chicago, returning Mon, 2 Feb, priced at ฿4,980 found 21 hours ago
Delta
Fri, 23 Jan - Tue, 27 Jan
BOS
Boston
ORD
Chicago
฿5,035 Return, found 9 hours ago
฿5,035
Return
found 9 hours ago
Select Delta flight, departing Fri, 23 Jan from Boston to Chicago, returning Tue, 27 Jan, priced at ฿5,035 found 9 hours ago
United
Fri, 30 Jan - Mon, 2 Feb
BOS
Boston
ORD
Chicago
฿5,135 Return, found 21 hours ago
฿5,135
Return
found 21 hours ago
Select United flight, departing Fri, 30 Jan from Boston to Chicago, returning Mon, 2 Feb, priced at ฿5,135 found 21 hours ago
Delta
Tue, 10 Feb - Thu, 26 Feb
BOS
Boston
ORD
Chicago
฿5,240 Return, found 3 days ago
฿5,240
Return
found 3 days ago
Select Delta flight, departing Tue, 10 Feb from Boston to Chicago, returning Thu, 26 Feb, priced at ฿5,240 found 3 days ago

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

January is typically the cheapest month to fly

From ฿2,913 - ฿5,186 per traveller.

Frequently asked questions

How much is a flight from Logan Intl. Airport to ORD?
If you're planning on travelling from BOS to O'Hare Airport, round-trip flights start from ฿3,855. This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport (BOS) to ORD?
The majority of flights can be conveniently cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from BOS to O'Hare Intl. Airport (ORD) 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 Logan Intl. Airport to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from BOS to O'Hare Intl. Airport (ORD)?
Forget about a movie marathon on this flight — it's only 1,400 kilometres from Boston to Chicago. Sit down, buckle up and you'll be touching down before long.
Which airlines fly direct from Logan Intl. Airport to ORD?
It's a breeze to fly directly from Logan Intl. Airport to ORD. Below are some of the top carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 230 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 Logan Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
It is possible to get great last-minute deals from BOS to O'Hare Airport, but it's also possible to miss out entirely! As many airlines publish prices up to a year in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you're always getting the latest offers.

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
฿3,855
Distance
1381 km
Average flight time
2 hours 5 mins

Book with confidence

Perfect flights from Boston to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Boston to Chicago. 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 , 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 Logan Intl. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿1,680 and roundtrip prices from ฿3,855. 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 O'Hare Intl. and explore 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 to travel arrangements today and embark on the journey of a lifetime in Chicago.
Perfect flights from Boston to Chicago
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