฿2,710 Cheap Flights from Chicago (CHI) to Boston (BOS)

View ฿2,710 flight on Wed, 27 May 2026Opens in a new window

Flight 1

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 and start at ฿2,710 for one-way flights and ฿5,575 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿5,575 Return, found 3 days ago
฿5,575
Return
found 3 days ago
Select Delta flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿5,575 found 3 days ago
Delta
Sat, 9 May - Sun, 10 May
ORD
Chicago
BOS
Boston
฿5,650 Return, found 3 days ago
฿5,650
Return
found 3 days ago
Select Delta flight, departing Sat, 9 May from Chicago to Boston, returning Sun, 10 May, priced at ฿5,650 found 3 days ago
Delta
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿6,220 Return, found 3 days ago
฿6,220
Return
found 3 days ago
Select Delta flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿6,220 found 3 days ago
Delta
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿6,380 Return, found 3 days ago
฿6,380
Return
found 3 days ago
Select Delta flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿6,380 found 3 days ago
Delta
Sat, 9 May - Sun, 10 May
ORD
Chicago
BOS
Boston
฿6,475 Return, found 3 days ago
฿6,475
Return
found 3 days ago
Select Delta flight, departing Sat, 9 May from Chicago to Boston, returning Sun, 10 May, priced at ฿6,475 found 3 days ago
American Airlines
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿6,710 Return, found 3 days ago
฿6,710
Return
found 3 days ago
Select American Airlines flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿6,710 found 3 days ago
American Airlines
Sat, 9 May - Sun, 10 May
ORD
Chicago
BOS
Boston
฿6,805 Return, found 3 days ago
฿6,805
Return
found 3 days ago
Select American Airlines flight, departing Sat, 9 May from Chicago to Boston, returning Sun, 10 May, priced at ฿6,805 found 3 days ago
United
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿6,870 Return, found 3 days ago
฿6,870
Return
found 3 days ago
Select United flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿6,870 found 3 days ago
Delta
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿7,025 Return, found 3 days ago
฿7,025
Return
found 3 days ago
Select Delta flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿7,025 found 3 days ago
American Airlines
Thu, 7 May - Wed, 13 May
ORD
Chicago
BOS
Boston
฿7,160 Return, found 3 days ago
฿7,160
Return
found 3 days ago
Select American Airlines flight, departing Thu, 7 May from Chicago to Boston, returning Wed, 13 May, priced at ฿7,160 found 3 days ago

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 ฿5,575. 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

Origin airport
O'Hare Intl.
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Return price
฿5,575
Distance
1381 km
*Available to Expedia members.