Cheap Flights from Boston (BOS) to Chicago (CHI) from HK$497~

View HK$497 flight on Wed, 10 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$497 for one-way flights and HK$993 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 18 Oct - Wed, 22 Oct
BOS
Boston
ORD
Chicago
HK$993 Return, found 6 days ago
HK$993
Return
found 6 days ago
Select Delta flight, departing Sat, 18 Oct from Boston to Chicago, returning Wed, 22 Oct, priced at HK$993 found 6 days ago
Delta
Sat, 18 Oct - Wed, 22 Oct
BOS
Boston
ORD
Chicago
HK$1,273 Return, found 6 days ago
HK$1,273
Return
found 6 days ago
Select Delta flight, departing Sat, 18 Oct from Boston to Chicago, returning Wed, 22 Oct, priced at HK$1,273 found 6 days ago
Delta
Sat, 15 Nov - Sat, 22 Nov
BOS
Boston
ORD
Chicago
HK$1,391 Return, found 6 days ago
HK$1,391
Return
found 6 days ago
Select Delta flight, departing Sat, 15 Nov from Boston to Chicago, returning Sat, 22 Nov, priced at HK$1,391 found 6 days ago
Delta
Mon, 22 Sept - Tue, 23 Sept
BOS
Boston
ORD
Chicago
HK$1,393 Return, found 1 day ago
HK$1,393
Return
found 1 day ago
Select Delta flight, departing Mon, 22 Sept from Boston to Chicago, returning Tue, 23 Sept, priced at HK$1,393 found 1 day ago
Delta
Sat, 18 Oct - Wed, 22 Oct
BOS
Boston
ORD
Chicago
HK$1,423 Return, found 6 days ago
HK$1,423
Return
found 6 days ago
Select Delta flight, departing Sat, 18 Oct from Boston to Chicago, returning Wed, 22 Oct, priced at HK$1,423 found 6 days ago
Delta
Fri, 17 Oct - Wed, 22 Oct
BOS
Boston
ORD
Chicago
HK$1,509 Return, found 6 days ago
HK$1,509
Return
found 6 days ago
Select Delta flight, departing Fri, 17 Oct from Boston to Chicago, returning Wed, 22 Oct, priced at HK$1,509 found 6 days ago
United
Sun, 21 Sept - Mon, 22 Sept
BOS
Boston
ORD
Chicago
HK$1,511 Return, found 1 day ago
HK$1,511
Return
found 1 day ago
Select United flight, departing Sun, 21 Sept from Boston to Chicago, returning Mon, 22 Sept, priced at HK$1,511 found 1 day ago
United
Thu, 18 Sept - Mon, 22 Sept
BOS
Boston
ORD
Chicago
HK$1,522 Return, found 3 days ago
HK$1,522
Return
found 3 days ago
Select United flight, departing Thu, 18 Sept from Boston to Chicago, returning Mon, 22 Sept, priced at HK$1,522 found 3 days ago
American Airlines
Sat, 18 Oct - Wed, 22 Oct
BOS
Boston
ORD
Chicago
HK$1,541 Return, found 6 days ago
HK$1,541
Return
found 6 days ago
Select American Airlines flight, departing Sat, 18 Oct from Boston to Chicago, returning Wed, 22 Oct, priced at HK$1,541 found 6 days ago
JetBlue Airways
Tue, 16 Sept - Wed, 24 Sept
BOS
Boston
ORD
Chicago
HK$1,543 Return, found 3 days ago
HK$1,543
Return
found 3 days ago
Select JetBlue Airways flight, departing Tue, 16 Sept from Boston to Chicago, returning Wed, 24 Sept, priced at HK$1,543 found 3 days ago

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

November is typically the cheapest month to fly

From HK$609 - HK$2,105 per traveller.
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
HK$993
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$497 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$993. 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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