₩81,500 Cheap Flights from Boston (BOS) to Chicago (ORD)

View ₩81,500 flight on Tue, Nov 4, 2025Opens in a new window

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

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Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at ₩81,500 for one-way flights and ₩176,700 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 29 - Sat, Nov 15
BOS
Boston
ORD
Chicago
₩176,700 Roundtrip, found 12 hours ago
₩176,700
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Oct 29 from Boston to Chicago, returning Sat, Nov 15, priced at ₩176,700 found 12 hours ago
Delta
Wed, Nov 19 - Sat, Dec 6
BOS
Boston
ORD
Chicago
₩190,600 Roundtrip, found 12 hours ago
₩190,600
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Nov 19 from Boston to Chicago, returning Sat, Dec 6, priced at ₩190,600 found 12 hours ago
Delta
Wed, Nov 19 - Sun, Dec 7
BOS
Boston
ORD
Chicago
₩204,400 Roundtrip, found 12 hours ago
₩204,400
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Nov 19 from Boston to Chicago, returning Sun, Dec 7, priced at ₩204,400 found 12 hours ago
Delta
Tue, Oct 7 - Wed, Oct 15
BOS
Boston
ORD
Chicago
₩204,700 Roundtrip, found 2 days ago
₩204,700
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 7 from Boston to Chicago, returning Wed, Oct 15, priced at ₩204,700 found 2 days ago
Delta
Thu, Nov 20 - Sun, Dec 7
BOS
Boston
ORD
Chicago
₩218,300 Roundtrip, found 12 hours ago
₩218,300
Roundtrip
found 12 hours ago
Select Delta flight, departing Thu, Nov 20 from Boston to Chicago, returning Sun, Dec 7, priced at ₩218,300 found 12 hours ago
Delta
Tue, Oct 28 - Wed, Oct 29
BOS
Boston
ORD
Chicago
₩218,400 Roundtrip, found 12 hours ago
₩218,400
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Oct 28 from Boston to Chicago, returning Wed, Oct 29, priced at ₩218,400 found 12 hours ago
Delta
Sun, Nov 23 - Sat, Dec 6
BOS
Boston
ORD
Chicago
₩232,200 Roundtrip, found 12 hours ago
₩232,200
Roundtrip
found 12 hours ago
Select Delta flight, departing Sun, Nov 23 from Boston to Chicago, returning Sat, Dec 6, priced at ₩232,200 found 12 hours ago
American Airlines
Wed, Oct 15 - Fri, Oct 17
BOS
Boston
ORD
Chicago
₩254,300 Roundtrip, found 1 day ago
₩254,300
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 15 from Boston to Chicago, returning Fri, Oct 17, priced at ₩254,300 found 1 day ago
United
Fri, Oct 3 - Sun, Oct 19
BOS
Boston
ORD
Chicago
₩260,000 Roundtrip, found 12 hours ago
₩260,000
Roundtrip
found 12 hours ago
Select United flight, departing Fri, Oct 3 from Boston to Chicago, returning Sun, Oct 19, priced at ₩260,000 found 12 hours ago
JetBlue Airways
Mon, Nov 3 - Sat, Nov 15
BOS
Boston
ORD
Chicago
₩266,900 Roundtrip, found 12 hours ago
₩266,900
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Mon, Nov 3 from Boston to Chicago, returning Sat, Nov 15, priced at ₩266,900 found 12 hours ago

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

November is typically the cheapest month to fly

From ₩122,100 - ₩370,673 per traveler.

Frequently asked questions

How much is a flight from Logan Intl. Airport to ORD?
If you're planning on traveling from BOS to O'Hare Airport, round-trip flights start from ₩176,700. 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 canceled 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 kilometers 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

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
₩176,700
Distance
1381 km

Book with confidence

Book with confidence

Boston to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Boston to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with BOS to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Boston for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Boston to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Boston nearby Airports

Providence

T.F. Green to Chicago
₩436,100
*Available to Expedia members.