฿2,265 Cheap Flights from Boston (BOS) to Chicago (CHI)

View ฿2,265 flight on Wed, 12 Nov 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago

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

Prices were available within the past 7 days and start at ฿2,265 for one-way flights and ฿4,200 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿4,200 Return, found 3 days ago
฿4,200
Return
found 3 days ago
Select Delta flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿4,200 found 3 days ago
Delta
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿4,525 Return, found 3 days ago
฿4,525
Return
found 3 days ago
Select Delta flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿4,525 found 3 days ago
United
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿5,020 Return, found 3 days ago
฿5,020
Return
found 3 days ago
Select United flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿5,020 found 3 days ago
United
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿5,195 Return, found 3 days ago
฿5,195
Return
found 3 days ago
Select United flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿5,195 found 3 days ago
United
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿5,350 Return, found 3 days ago
฿5,350
Return
found 3 days ago
Select United flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿5,350 found 3 days ago
United
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿5,525 Return, found 3 days ago
฿5,525
Return
found 3 days ago
Select United flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿5,525 found 3 days ago
Delta
Sat, 25 Oct - Mon, 27 Oct
BOS
Boston
ORD
Chicago
฿5,845 Return, found 1 day ago
฿5,845
Return
found 1 day ago
Select Delta flight, departing Sat, 25 Oct from Boston to Chicago, returning Mon, 27 Oct, priced at ฿5,845 found 1 day ago
American Airlines
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿5,945 Return, found 3 days ago
฿5,945
Return
found 3 days ago
Select American Airlines flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿5,945 found 3 days ago
Delta
Sat, 25 Oct - Mon, 27 Oct
BOS
Boston
ORD
Chicago
฿6,010 Return, found 1 day ago
฿6,010
Return
found 1 day ago
Select Delta flight, departing Sat, 25 Oct from Boston to Chicago, returning Mon, 27 Oct, priced at ฿6,010 found 1 day ago
American Airlines
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
฿6,170 Return, found 3 days ago
฿6,170
Return
found 3 days ago
Select American Airlines flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at ฿6,170 found 3 days ago

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

September is typically the cheapest month to fly

From ฿2,691 - ฿5,472 per traveller.
Flight from Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
฿4,200
Distance
1381 km

Perfect flights from Boston to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Boston to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Logan Intl. to CHI-All Airports ticket options cater to your travel preferences, with incredible one-way fares from ฿2,265 and roundtrip prices from ฿4,200. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at CHI-All Airports and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.

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 ฿4,200. 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 kilometres. 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Boston to O'Hare Intl.
฿4,200.00
*Available to Expedia members.