RM395 Cheap Flights from Boston (BOS) to Chicago (ORD)

View RM395 flight on Sun, 9 Nov 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 RM395 for one-way flights and RM2,542 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,542 Return, found 6 days ago
RM2,542
Return
found 6 days ago
Select United flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,542 found 6 days ago
United
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,583 Return, found 6 days ago
RM2,583
Return
found 6 days ago
Select United flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,583 found 6 days ago
American Airlines
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,612 Return, found 6 days ago
RM2,612
Return
found 6 days ago
Select American Airlines flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,612 found 6 days ago
Delta
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,625 Return, found 6 days ago
RM2,625
Return
found 6 days ago
Select Delta flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,625 found 6 days ago
American Airlines
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,653 Return, found 6 days ago
RM2,653
Return
found 6 days ago
Select American Airlines flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,653 found 6 days ago
American Airlines
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,689 Return, found 6 days ago
RM2,689
Return
found 6 days ago
Select American Airlines flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,689 found 6 days ago
American Airlines
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,730 Return, found 6 days ago
RM2,730
Return
found 6 days ago
Select American Airlines flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,730 found 6 days ago
Delta
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,775 Return, found 6 days ago
RM2,775
Return
found 6 days ago
Select Delta flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,775 found 6 days ago
United
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,796 Return, found 6 days ago
RM2,796
Return
found 6 days ago
Select United flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,796 found 6 days ago
United
Fri, 28 Nov - Sun, 30 Nov
BOS
Boston
ORD
Chicago
RM2,820 Return, found 6 days ago
RM2,820
Return
found 6 days ago
Select United flight, departing Fri, 28 Nov from Boston to Chicago, returning Sun, 30 Nov, priced at RM2,820 found 6 days ago

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

September is typically the cheapest month to fly

From RM 383 - RM 575 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 RM2,542. 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.
Return price
RM2,542
Distance
1381 km
Average flight time
1 hour 52 mins

Book with confidence

Perfect flights from Boston to Chicago

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Boston to Chicago

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