Cheap Flights from Boston (BOS) to Chicago (ORD) from HK$530~

View HK$530 flight on Sat, 9 May 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at HK$530 for one-way flights and HK$1,059 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 10 Mar - Wed, 11 Mar
BOS
Boston
ORD
Chicago
HK$1,059 Return, found 1 day ago
HK$1,059
Return
found 1 day ago
Select Delta flight, departing Tue, 10 Mar from Boston to Chicago, returning Wed, 11 Mar, priced at HK$1,059 found 1 day ago
Delta
Tue, 10 Feb - Tue, 17 Feb
BOS
Boston
ORD
Chicago
HK$1,070 Return, found 1 day ago
HK$1,070
Return
found 1 day ago
Select Delta flight, departing Tue, 10 Feb from Boston to Chicago, returning Tue, 17 Feb, priced at HK$1,070 found 1 day ago
Delta
Tue, 10 Feb - Sat, 14 Feb
BOS
Boston
ORD
Chicago
HK$1,081 Return, found 1 day ago
HK$1,081
Return
found 1 day ago
Select Delta flight, departing Tue, 10 Feb from Boston to Chicago, returning Sat, 14 Feb, priced at HK$1,081 found 1 day ago
Delta
Thu, 26 Feb - Sat, 28 Feb
BOS
Boston
ORD
Chicago
HK$1,083 Return, found 3 days ago
HK$1,083
Return
found 3 days ago
Select Delta flight, departing Thu, 26 Feb from Boston to Chicago, returning Sat, 28 Feb, priced at HK$1,083 found 3 days ago
Delta
Tue, 10 Feb - Mon, 16 Feb
BOS
Boston
ORD
Chicago
HK$1,156 Return, found 1 day ago
HK$1,156
Return
found 1 day ago
Select Delta flight, departing Tue, 10 Feb from Boston to Chicago, returning Mon, 16 Feb, priced at HK$1,156 found 1 day ago
Delta
Wed, 4 Feb - Tue, 17 Feb
BOS
Boston
ORD
Chicago
HK$1,231 Return, found 5 days ago
HK$1,231
Return
found 5 days ago
Select Delta flight, departing Wed, 4 Feb from Boston to Chicago, returning Tue, 17 Feb, priced at HK$1,231 found 5 days ago
Delta
Thu, 26 Feb - Sat, 28 Feb
BOS
Boston
ORD
Chicago
HK$1,244 Return, found 3 days ago
HK$1,244
Return
found 3 days ago
Select Delta flight, departing Thu, 26 Feb from Boston to Chicago, returning Sat, 28 Feb, priced at HK$1,244 found 3 days ago
Delta
Tue, 10 Mar - Thu, 12 Mar
BOS
Boston
ORD
Chicago
HK$1,264 Return, found 1 day ago
HK$1,264
Return
found 1 day ago
Select Delta flight, departing Tue, 10 Mar from Boston to Chicago, returning Thu, 12 Mar, priced at HK$1,264 found 1 day ago
American Airlines
Sat, 7 Feb - Mon, 9 Feb
BOS
Boston
ORD
Chicago
HK$1,501 Return, found 5 days ago
HK$1,501
Return
found 5 days ago
Select American Airlines flight, departing Sat, 7 Feb from Boston to Chicago, returning Mon, 9 Feb, priced at HK$1,501 found 5 days ago
United
Wed, 25 Feb - Sun, 1 Mar
BOS
Boston
ORD
Chicago
HK$1,610 Return, found 3 days ago
HK$1,610
Return
found 3 days ago
Select United flight, departing Wed, 25 Feb from Boston to Chicago, returning Sun, 1 Mar, priced at HK$1,610 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 HK$708 - HK$1,261 per traveller.
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
HK$1,059
Distance
1381 km
Average flight time
2 hours 4 mins

Flights from Boston to Chicago

Book cheap flights from Boston (BOS) to Chicago (ORD) on Expedia.com.hk. Find the best flight deals to destinations around the world for your next leisure or business travel on Expedia.com.hk.

Search for flights from Boston (BOS) to Chicago (ORD) to find great flight deals suitable to your travel date and time. Expedia.com.hk flight booking search engine is simple to use and looking for cheap flights is as easy as a click of a mouse or on your mobile devices.

Be assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Boston (BOS) to Chicago (ORD) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

Save more when combine your Chicago flight with a hotel for a package deal! Discover additional savings by booking in advance. Now you can find activities in Chicago and things to do in Chicago for your perfect vacation with Expedia Thing to Do.

If you would like to book flights to Chicago more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is HK$530 now!

 

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 HK$1,059. 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.

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