฿1,935 Cheap Flights from Chicago (CHI) to Boston (BOS)

View ฿1,935 flight on Wed, 19 Nov 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 and start at ฿1,935 for one-way flights and ฿5,185 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 22 Oct - Wed, 29 Oct
ORD
Chicago
BOS
Boston
฿5,185 Return, found 3 days ago
฿5,185
Return
found 3 days ago
Select Delta flight, departing Wed, 22 Oct from Chicago to Boston, returning Wed, 29 Oct, priced at ฿5,185 found 3 days ago
JetBlue Airways
Wed, 22 Oct - Tue, 28 Oct
ORD
Chicago
BOS
Boston
฿5,845 Return, found 3 days ago
฿5,845
Return
found 3 days ago
Select JetBlue Airways flight, departing Wed, 22 Oct from Chicago to Boston, returning Tue, 28 Oct, priced at ฿5,845 found 3 days ago
Delta
Fri, 24 Oct - Wed, 29 Oct
ORD
Chicago
BOS
Boston
฿6,075 Return, found 3 days ago
฿6,075
Return
found 3 days ago
Select Delta flight, departing Fri, 24 Oct from Chicago to Boston, returning Wed, 29 Oct, priced at ฿6,075 found 3 days ago
American Airlines
Fri, 24 Oct - Sat, 25 Oct
ORD
Chicago
BOS
Boston
฿6,170 Return, found 3 days ago
฿6,170
Return
found 3 days ago
Select American Airlines flight, departing Fri, 24 Oct from Chicago to Boston, returning Sat, 25 Oct, priced at ฿6,170 found 3 days ago
United
Fri, 31 Oct - Tue, 4 Nov
ORD
Chicago
BOS
Boston
฿6,275 Return, found 2 days ago
฿6,275
Return
found 2 days ago
Select United flight, departing Fri, 31 Oct from Chicago to Boston, returning Tue, 4 Nov, priced at ฿6,275 found 2 days ago
United
Fri, 31 Oct - Tue, 4 Nov
ORD
Chicago
BOS
Boston
฿6,600 Return, found 2 days ago
฿6,600
Return
found 2 days ago
Select United flight, departing Fri, 31 Oct from Chicago to Boston, returning Tue, 4 Nov, priced at ฿6,600 found 2 days ago
Delta
Wed, 22 Oct - Fri, 24 Oct
ORD
Chicago
BOS
Boston
฿6,730 Return, found 3 days ago
฿6,730
Return
found 3 days ago
Select Delta flight, departing Wed, 22 Oct from Chicago to Boston, returning Fri, 24 Oct, priced at ฿6,730 found 3 days ago
United
Fri, 31 Oct - Tue, 4 Nov
ORD
Chicago
BOS
Boston
฿6,775 Return, found 2 days ago
฿6,775
Return
found 2 days ago
Select United flight, departing Fri, 31 Oct from Chicago to Boston, returning Tue, 4 Nov, priced at ฿6,775 found 2 days ago
United
Thu, 16 Jul - Wed, 22 Jul
ORD
Chicago
BOS
Boston
฿6,835 Return, found 2 days ago
฿6,835
Return
found 2 days ago
Select United flight, departing Thu, 16 Jul from Chicago to Boston, returning Wed, 22 Jul, priced at ฿6,835 found 2 days ago
American Airlines
Thu, 16 Jul - Wed, 22 Jul
ORD
Chicago
BOS
Boston
฿6,840 Return, found 2 days ago
฿6,840
Return
found 2 days ago
Select American Airlines flight, departing Thu, 16 Jul from Chicago to Boston, returning Wed, 22 Jul, priced at ฿6,840 found 2 days ago

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

September is typically the cheapest month to fly

From ฿2,691 - ฿4,560 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 ฿5,185. 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.
Return price
฿5,185
Distance
1381 km

Book with confidence

Illinois to Boston Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Illinois to Boston will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Boston.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with CHI to BOS flights that won’t make your bank account wince. Ready to temporarily leave behind Illinois for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to BOS with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Illinois to Boston Flights

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Boston
฿5,185.00
*Available to Expedia members.