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RM599 Cheap Flights from Boston (BOS) to Chicago (ORD)

View RM599 flight on Fri, 13 Nov 2026Opens 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 RM599 for one-way flights and RM1,488 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,488 Return, found 2 hours ago
RM1,488
Return
found 2 hours ago
Select Delta flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,488 found 2 hours ago
Delta
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,529 Return, found 2 hours ago
RM1,529
Return
found 2 hours ago
Select Delta flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,529 found 2 hours ago
Delta
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,569 Return, found 2 hours ago
RM1,569
Return
found 2 hours ago
Select Delta flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,569 found 2 hours ago
American Airlines
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,605 Return, found 2 hours ago
RM1,605
Return
found 2 hours ago
Select American Airlines flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,605 found 2 hours ago
American Airlines
Thu, 17 Sept - Thu, 24 Sept
BOS
Boston
ORD
Chicago
RM1,646 Return, found 2 hours ago
RM1,646
Return
found 2 hours ago
Select American Airlines flight, departing Thu, 17 Sept from Boston to Chicago, returning Thu, 24 Sept, priced at RM1,646 found 2 hours ago
Delta
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,650 Return, found 2 hours ago
RM1,650
Return
found 2 hours ago
Select Delta flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,650 found 2 hours ago
Delta
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,651 Return, found 2 hours ago
RM1,651
Return
found 2 hours ago
Select Delta flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,651 found 2 hours ago
Delta
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,671 Return, found 2 hours ago
RM1,671
Return
found 2 hours ago
Select Delta flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,671 found 2 hours ago
American Airlines
Thu, 17 Sept - Thu, 24 Sept
BOS
Boston
ORD
Chicago
RM1,687 Return, found 2 hours ago
RM1,687
Return
found 2 hours ago
Select American Airlines flight, departing Thu, 17 Sept from Boston to Chicago, returning Thu, 24 Sept, priced at RM1,687 found 2 hours ago
United
Thu, 17 Sept - Sun, 20 Sept
BOS
Boston
ORD
Chicago
RM1,881 Return, found 2 hours ago
RM1,881
Return
found 2 hours ago
Select United flight, departing Thu, 17 Sept from Boston to Chicago, returning Sun, 20 Sept, priced at RM1,881 found 2 hours ago

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

September is typically the cheapest month to fly

From RM 575 - RM 812 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 RM1,488. 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
RM1,488
Distance
1381 km
Average flight time
1 hour 53 mins

Book with confidence

Perfect flights from Boston to Chicago

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Experience the joy of finding cheap flights from Logan Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from RM599 and roundtrip prices from RM1,488*.
 

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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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