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

View AU$89 flight on Mon, 20 Oct 2025Opens in a new window

Popular airlines from Chicago to Boston, MA (BOS-Logan Intl.)

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

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 1 Nov - Sat, 8 Nov
ORD
Chicago
BOS
Boston
AU$177 Return, found 1 day ago
AU$177
Return
found 1 day ago
Select American Airlines flight, departing Sat, 1 Nov from Chicago to Boston, returning Sat, 8 Nov, priced at AU$177 found 1 day ago
Delta
Wed, 29 Oct - Wed, 5 Nov
ORD
Chicago
BOS
Boston
AU$178 Return, found 3 days ago
AU$178
Return
found 3 days ago
Select Delta flight, departing Wed, 29 Oct from Chicago to Boston, returning Wed, 5 Nov, priced at AU$178 found 3 days ago
American Airlines
Wed, 29 Oct - Wed, 5 Nov
ORD
Chicago
BOS
Boston
AU$178 Return, found 3 days ago
AU$178
Return
found 3 days ago
Select American Airlines flight, departing Wed, 29 Oct from Chicago to Boston, returning Wed, 5 Nov, priced at AU$178 found 3 days ago
Delta
Sat, 1 Nov - Sat, 8 Nov
ORD
Chicago
BOS
Boston
AU$192 Return, found 1 day ago
AU$192
Return
found 1 day ago
Select Delta flight, departing Sat, 1 Nov from Chicago to Boston, returning Sat, 8 Nov, priced at AU$192 found 1 day ago
American Airlines
Sat, 1 Nov - Sat, 8 Nov
ORD
Chicago
BOS
Boston
AU$218 Return, found 1 day ago
AU$218
Return
found 1 day ago
Select American Airlines flight, departing Sat, 1 Nov from Chicago to Boston, returning Sat, 8 Nov, priced at AU$218 found 1 day ago
American Airlines
Fri, 17 Oct - Tue, 21 Oct
ORD
Chicago
BOS
Boston
AU$220 Return, found 3 days ago
AU$220
Return
found 3 days ago
Select American Airlines flight, departing Fri, 17 Oct from Chicago to Boston, returning Tue, 21 Oct, priced at AU$220 found 3 days ago
Delta
Fri, 17 Oct - Tue, 21 Oct
ORD
Chicago
BOS
Boston
AU$223 Return, found 3 days ago
AU$223
Return
found 3 days ago
Select Delta flight, departing Fri, 17 Oct from Chicago to Boston, returning Tue, 21 Oct, priced at AU$223 found 3 days ago
United
Wed, 29 Oct - Wed, 5 Nov
ORD
Chicago
BOS
Boston
AU$231 Return, found 3 days ago
AU$231
Return
found 3 days ago
Select United flight, departing Wed, 29 Oct from Chicago to Boston, returning Wed, 5 Nov, priced at AU$231 found 3 days ago
Delta
Sat, 1 Nov - Sat, 8 Nov
ORD
Chicago
BOS
Boston
AU$237 Return, found 1 day ago
AU$237
Return
found 1 day ago
Select Delta flight, departing Sat, 1 Nov from Chicago to Boston, returning Sat, 8 Nov, priced at AU$237 found 1 day ago
United
Sat, 1 Nov - Sat, 8 Nov
ORD
Chicago
BOS
Boston
AU$238 Return, found 1 day ago
AU$238
Return
found 1 day ago
Select United flight, departing Sat, 1 Nov from Chicago to Boston, returning Sat, 8 Nov, priced at AU$238 found 1 day ago

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

September is typically the cheapest month to fly

From AU$127 - AU$265 per traveller.

Frequently asked questions

How much is a flight from Chicago, IL (CHI-All Airports) to BOS?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip flights from Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS) start from AU$177. Book now to score the best price for your trip. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS)?
Every air carrier has its own terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS) 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 Chicago, IL (CHI-All Airports) to BOS flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Chicago, IL (CHI-All Airports) to BOS?
That new movie you've been wanting to see will have to wait — the flight distance between Chicago, IL (CHI-All Airports) and Logan Intl. Airport (BOS) is only 1 450 kilometres. The captain will be telling you to buckle up for landing before you know it.
Which airlines fly direct from Chicago, IL (CHI-All Airports) to BOS?
You have plenty of choices when flying from Chicago, IL (CHI-All Airports) to BOS. Lock in your fare with one of these reputable carriers:

  • American Airlines - (AA) with 225 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 Chicago, IL (CHI-All Airports) to Logan Intl. Airport (BOS) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Chicago, IL (CHI-All Airports) to Logan Intl. Airport last minute could save you some cash. However, it could end up costing you a whole lot more! If you'd rather play it safe, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Return price
AU$176
Distance
1381 km

Book with confidence

Book with confidence

CHI to BOS Flights

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CHI to BOS Flights

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