Cheap Flights from Boston (BOS) to Chicago (CHI) from HK$540~

View HK$540 flight on Fri, 6 Feb 2026Opens in a new window

Popular airlines from Boston 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$540 for one-way flights and HK$1,068 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
HK$1,068 Return, found 10 hours ago
HK$1,068
Return
found 10 hours ago
Select Delta flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at HK$1,068 found 10 hours ago
Delta
Fri, 6 Feb - Fri, 13 Feb
BOS
Boston
ORD
Chicago
HK$1,229 Return, found 4 hours ago
HK$1,229
Return
found 4 hours ago
Select Delta flight, departing Fri, 6 Feb from Boston to Chicago, returning Fri, 13 Feb, priced at HK$1,229 found 4 hours ago
United
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
HK$1,316 Return, found 10 hours ago
HK$1,316
Return
found 10 hours ago
Select United flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at HK$1,316 found 10 hours ago
Delta
Fri, 6 Feb - Fri, 13 Feb
BOS
Boston
ORD
Chicago
HK$1,348 Return, found 4 hours ago
HK$1,348
Return
found 4 hours ago
Select Delta flight, departing Fri, 6 Feb from Boston to Chicago, returning Fri, 13 Feb, priced at HK$1,348 found 4 hours ago
Delta
Fri, 6 Feb - Fri, 13 Feb
BOS
Boston
ORD
Chicago
HK$1,380 Return, found 4 hours ago
HK$1,380
Return
found 4 hours ago
Select Delta flight, departing Fri, 6 Feb from Boston to Chicago, returning Fri, 13 Feb, priced at HK$1,380 found 4 hours ago
United
Tue, 6 Jan - Sat, 10 Jan
BOS
Boston
ORD
Chicago
HK$1,466 Return, found 2 days ago
HK$1,466
Return
found 2 days ago
Select United flight, departing Tue, 6 Jan from Boston to Chicago, returning Sat, 10 Jan, priced at HK$1,466 found 2 days ago
United
Fri, 6 Feb - Fri, 13 Feb
BOS
Boston
ORD
Chicago
HK$1,498 Return, found 4 hours ago
HK$1,498
Return
found 4 hours ago
Select United flight, departing Fri, 6 Feb from Boston to Chicago, returning Fri, 13 Feb, priced at HK$1,498 found 4 hours ago
Delta
Fri, 6 Feb - Fri, 13 Feb
BOS
Boston
ORD
Chicago
HK$1,510 Return, found 4 hours ago
HK$1,510
Return
found 4 hours ago
Select Delta flight, departing Fri, 6 Feb from Boston to Chicago, returning Fri, 13 Feb, priced at HK$1,510 found 4 hours ago
Delta
Fri, 6 Feb - Fri, 13 Feb
BOS
Boston
ORD
Chicago
HK$1,541 Return, found 4 hours ago
HK$1,541
Return
found 4 hours ago
Select Delta flight, departing Fri, 6 Feb from Boston to Chicago, returning Fri, 13 Feb, priced at HK$1,541 found 4 hours ago
American Airlines
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
HK$1,584 Return, found 10 hours ago
HK$1,584
Return
found 10 hours ago
Select American Airlines flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at HK$1,584 found 10 hours ago

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

September is typically the cheapest month to fly

From HK$651 - HK$1,423 per traveller.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from HK$1,229
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from HK$1,229

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$1,068. 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.

Travel information

Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
HK$1,068
Distance
1381 km

Book with confidence

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$540 now!

 

Flights from Boston to Illinois

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