Cheap Flights from Boston (BOS) to Chicago (CHI) from HK$464~

View HK$464 flight on Tue, 9 Dec 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago

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

Prices were available within the past 7 days and start at HK$464 for one-way flights and HK$971 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 11 Dec - Thu, 18 Dec
BOS
Boston
ORD
Chicago
HK$971 Return, found 3 days ago
HK$971
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Dec from Boston to Chicago, returning Thu, 18 Dec, priced at HK$971 found 3 days ago
Delta
Wed, 19 Nov - Wed, 3 Dec
BOS
Boston
ORD
Chicago
HK$993 Return, found 4 days ago
HK$993
Return
found 4 days ago
Select Delta flight, departing Wed, 19 Nov from Boston to Chicago, returning Wed, 3 Dec, priced at HK$993 found 4 days ago
Delta
Thu, 11 Dec - Thu, 18 Dec
BOS
Boston
ORD
Chicago
HK$1,047 Return, found 3 days ago
HK$1,047
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Dec from Boston to Chicago, returning Thu, 18 Dec, priced at HK$1,047 found 3 days ago
Delta
Tue, 18 Nov - Wed, 3 Dec
BOS
Boston
ORD
Chicago
HK$1,068 Return, found 4 days ago
HK$1,068
Return
found 4 days ago
Select Delta flight, departing Tue, 18 Nov from Boston to Chicago, returning Wed, 3 Dec, priced at HK$1,068 found 4 days ago
Delta
Thu, 20 Nov - Wed, 3 Dec
BOS
Boston
ORD
Chicago
HK$1,154 Return, found 4 days ago
HK$1,154
Return
found 4 days ago
Select Delta flight, departing Thu, 20 Nov from Boston to Chicago, returning Wed, 3 Dec, priced at HK$1,154 found 4 days ago
United
Thu, 11 Dec - Thu, 18 Dec
BOS
Boston
ORD
Chicago
HK$1,251 Return, found 3 days ago
HK$1,251
Return
found 3 days ago
Select United flight, departing Thu, 11 Dec from Boston to Chicago, returning Thu, 18 Dec, priced at HK$1,251 found 3 days ago
Delta
Thu, 11 Dec - Thu, 18 Dec
BOS
Boston
ORD
Chicago
HK$1,327 Return, found 3 days ago
HK$1,327
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Dec from Boston to Chicago, returning Thu, 18 Dec, priced at HK$1,327 found 3 days ago
Delta
Thu, 11 Dec - Thu, 18 Dec
BOS
Boston
ORD
Chicago
HK$1,380 Return, found 3 days ago
HK$1,380
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Dec from Boston to Chicago, returning Thu, 18 Dec, priced at HK$1,380 found 3 days ago
Delta
Fri, 21 Nov - Wed, 3 Dec
BOS
Boston
ORD
Chicago
HK$1,391 Return, found 4 days ago
HK$1,391
Return
found 4 days ago
Select Delta flight, departing Fri, 21 Nov from Boston to Chicago, returning Wed, 3 Dec, priced at HK$1,391 found 4 days ago
American Airlines
Thu, 11 Dec - Thu, 18 Dec
BOS
Boston
ORD
Chicago
HK$1,606 Return, found 3 days ago
HK$1,606
Return
found 3 days ago
Select American Airlines flight, departing Thu, 11 Dec from Boston to Chicago, returning Thu, 18 Dec, priced at HK$1,606 found 3 days ago

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

September is typically the cheapest month to fly

From HK$645 - HK$1,312 per traveller.
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
HK$971
Distance
1381 km

Flights from Boston to Illinois

Book cheap flights from Boston (BOS) to Illinois (CHI) 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 Illinois (CHI) 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 Illinois (CHI) trip. Call us at 3077-4857 (direct number - 24 hours day for English).

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

If you would like to book flights to Illinois more flexibly, many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Illinois is HK$464 now!

 

Frequently asked questions

How much is a flight from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)?
Pack your bags, because round-trip journeys from Logan Intl. Airport to Chicago, IL (CHI-All Airports) start from HK$971. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to get the best deal. 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 to Chicago, IL (CHI-All Airports)?
Each air carrier has its own terms and conditions. If you decide to cancel your trip, visit our Customer Service Portal.
How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports) 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 Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)?
The distance from Logan Intl. Airport (BOS) (BOS) to Chicago, IL (CHI-All Airports) (CHI) is 1,450 kilometers. You'll be stepping off the plane and collecting your baggage from the carousel in next to no time.
Which airlines fly direct from BOS to Chicago, IL (CHI-All Airports)?
With so many airlines to choose from, you'll be able to find your perfect flight from Logan Intl. Airport to Chicago, IL (CHI-All Airports) in a few clicks. These are some of the most popular carriers that fly directly between these airports:

  • American Airlines - (AA) with 230 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • Southwest Airlines - (WN) with 121 monthly flights

Are BOS to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
It is possible to find a great last-minute deal from BOS to Chicago, IL (CHI-All Airports), but there's no guarantee. As many airlines release prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals often, so you can rest easy knowing you're always seeing the latest offers.

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