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

View AU$98 flight on Wed, 24 Sept 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, 13 Dec - Wed, 17 Dec
ORD
Chicago
BOS
Boston
AU$195 Return, found 4 days ago
AU$195
Return
found 4 days ago
Select American Airlines flight, departing Sat, 13 Dec from Chicago to Boston, returning Wed, 17 Dec, priced at AU$195 found 4 days ago
Delta
Sat, 13 Dec - Wed, 17 Dec
ORD
Chicago
BOS
Boston
AU$195 Return, found 4 days ago
AU$195
Return
found 4 days ago
Select Delta flight, departing Sat, 13 Dec from Chicago to Boston, returning Wed, 17 Dec, priced at AU$195 found 4 days ago
American Airlines
Tue, 18 Nov - Tue, 9 Dec
ORD
Chicago
BOS
Boston
AU$196 Return, found 5 days ago
AU$196
Return
found 5 days ago
Select American Airlines flight, departing Tue, 18 Nov from Chicago to Boston, returning Tue, 9 Dec, priced at AU$196 found 5 days ago
Delta
Thu, 6 Nov - Wed, 12 Nov
ORD
Chicago
BOS
Boston
AU$211 Return, found 2 days ago
AU$211
Return
found 2 days ago
Select Delta flight, departing Thu, 6 Nov from Chicago to Boston, returning Wed, 12 Nov, priced at AU$211 found 2 days ago
American Airlines
Fri, 12 Dec - Fri, 9 Jan
ORD
Chicago
BOS
Boston
AU$226 Return, found 5 days ago
AU$226
Return
found 5 days ago
Select American Airlines flight, departing Fri, 12 Dec from Chicago to Boston, returning Fri, 9 Jan, priced at AU$226 found 5 days ago
American Airlines
Thu, 30 Oct - Wed, 5 Nov
ORD
Chicago
BOS
Boston
AU$239 Return, found 1 day ago
AU$239
Return
found 1 day ago
Select American Airlines flight, departing Thu, 30 Oct from Chicago to Boston, returning Wed, 5 Nov, priced at AU$239 found 1 day ago
Delta
Sat, 18 Oct - Sat, 25 Oct
ORD
Chicago
BOS
Boston
AU$241 Return, found 2 days ago
AU$241
Return
found 2 days ago
Select Delta flight, departing Sat, 18 Oct from Chicago to Boston, returning Sat, 25 Oct, priced at AU$241 found 2 days ago
Delta
Thu, 6 Nov - Thu, 13 Nov
ORD
Chicago
BOS
Boston
AU$242 Return, found 1 day ago
AU$242
Return
found 1 day ago
Select Delta flight, departing Thu, 6 Nov from Chicago to Boston, returning Thu, 13 Nov, priced at AU$242 found 1 day ago
United
Thu, 30 Oct - Wed, 5 Nov
ORD
Chicago
BOS
Boston
AU$315 Return, found 1 day ago
AU$315
Return
found 1 day ago
Select United flight, departing Thu, 30 Oct from Chicago to Boston, returning Wed, 5 Nov, priced at AU$315 found 1 day ago
Alaska Airlines
Sat, 18 Oct - Sat, 25 Oct
ORD
Chicago
BOS
Boston
AU$817 Return, found 2 days ago
AU$817
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 18 Oct from Chicago to Boston, returning Sat, 25 Oct, priced at AU$817 found 2 days ago

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

November is typically the cheapest month to fly

From AU$120 - AU$416 per traveller.
Flight from Chicago to Boston route information
Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Return price
AU$194
Distance
1381 km

CHI to BOS Flights

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Our user-friendly tools make it easier than ever to book CHI to BOS flights, even if you’re hoping to hop aboard one of the last-minute flights leaving today. So whether you seek a spontaneous trip to this city’s hottest attractions, or prefer to plan out every detail of your adventure ahead of time, Expedia.com.au is here to help you find exactly what you are interested in.

If you’re on the hunt for cheap flights to Boston from Illinois, you need not look any further. We make it simple for you to compare different airline carriers or choose the one that appeals to you most. We work with dozens of airlines in order to offer you incredible deals on business and personal travel. Start by searching through our selection of plane tickets today, and you’ll be in the sky before you know it.

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$195. 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.

Explore a world of travel with Expedia

Boston Flight Deals

Providence

Chicago Airports

Chicago

O'Hare Intl. to Boston
AU$194.30

Milwaukee

General Mitchell Intl. to Boston
AU$316.60
*Available to Expedia members.