฿2,240 Cheap Flights from Boston (BOS) to Chicago (ORD)

View ฿2,240 flight on Sun, 31 Aug 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD)

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

Prices were available within the past 7 days and start at ฿2,240 for one-way flights and ฿4,470 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿4,470 Return, found 11 hours ago
฿4,470
Return
found 11 hours ago
Select Delta flight, departing Sun, 31 Aug from Boston to Chicago, returning Fri, 5 Sep, priced at ฿4,470 found 11 hours ago
Delta
Fri, 24 Oct - Mon, 27 Oct
BOS
Boston
ORD
Chicago
฿4,790 Return, found 3 days ago
฿4,790
Return
found 3 days ago
Select Delta flight, departing Fri, 24 Oct from Boston to Chicago, returning Mon, 27 Oct, priced at ฿4,790 found 3 days ago
Delta
Sun, 14 Sep - Tue, 16 Sep
BOS
Boston
ORD
Chicago
฿5,070 Return, found 6 days ago
฿5,070
Return
found 6 days ago
Select Delta flight, departing Sun, 14 Sep from Boston to Chicago, returning Tue, 16 Sep, priced at ฿5,070 found 6 days ago
Delta
Fri, 24 Oct - Mon, 27 Oct
BOS
Boston
ORD
Chicago
฿5,280 Return, found 3 days ago
฿5,280
Return
found 3 days ago
Select Delta flight, departing Fri, 24 Oct from Boston to Chicago, returning Mon, 27 Oct, priced at ฿5,280 found 3 days ago
Delta
Tue, 2 Sep - Thu, 4 Sep
BOS
Boston
ORD
Chicago
฿5,450 Return, found 3 days ago
฿5,450
Return
found 3 days ago
Select Delta flight, departing Tue, 2 Sep from Boston to Chicago, returning Thu, 4 Sep, priced at ฿5,450 found 3 days ago
American Airlines
Sun, 31 Aug - Fri, 5 Sep
BOS
Boston
ORD
Chicago
฿5,610 Return, found 11 hours ago
฿5,610
Return
found 11 hours ago
Select American Airlines flight, departing Sun, 31 Aug from Boston to Chicago, returning Fri, 5 Sep, priced at ฿5,610 found 11 hours ago
United
Sun, 14 Sep - Tue, 16 Sep
BOS
Boston
ORD
Chicago
฿5,630 Return, found 6 days ago
฿5,630
Return
found 6 days ago
Select United flight, departing Sun, 14 Sep from Boston to Chicago, returning Tue, 16 Sep, priced at ฿5,630 found 6 days ago
Delta
Fri, 24 Oct - Mon, 27 Oct
BOS
Boston
ORD
Chicago
฿5,770 Return, found 3 days ago
฿5,770
Return
found 3 days ago
Select Delta flight, departing Fri, 24 Oct from Boston to Chicago, returning Mon, 27 Oct, priced at ฿5,770 found 3 days ago
Delta
Tue, 2 Sep - Thu, 4 Sep
BOS
Boston
ORD
Chicago
฿5,930 Return, found 3 days ago
฿5,930
Return
found 3 days ago
Select Delta flight, departing Tue, 2 Sep from Boston to Chicago, returning Thu, 4 Sep, priced at ฿5,930 found 3 days ago
American Airlines
Tue, 2 Sep - Thu, 4 Sep
BOS
Boston
ORD
Chicago
฿6,090 Return, found 3 days ago
฿6,090
Return
found 3 days ago
Select American Airlines flight, departing Tue, 2 Sep from Boston to Chicago, returning Thu, 4 Sep, priced at ฿6,090 found 3 days ago

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

September is typically the cheapest month to fly

From ฿1,815 - ฿3,786 per traveller.

Graph displaying average flight prices per month

Flight from Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Return price
฿4,470
Distance
1381 km
Average flight time
1 hour 52 mins

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 Chicago, 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 O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿2,240 and roundtrip prices from ฿4,470. 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 O'Hare Intl. and explore Chicago 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 BOS to ORD 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 to ORD?
If you're planning on travelling from BOS to O'Hare Airport, round-trip flights start from ฿4,470. This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book now and save yourself both money and time. 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 (BOS) to ORD?
The majority of flights can be conveniently cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from BOS to O'Hare Intl. Airport (ORD) 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 O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from BOS to O'Hare Intl. Airport (ORD)?
Forget about a movie marathon on this flight — it's only 1,400 kilometres from Boston to Chicago. Sit down, buckle up and you'll be touching down before long.
Which airlines fly direct from Logan Intl. Airport to ORD?
It's a breeze to fly directly from Logan Intl. Airport to ORD. Below are some of the top carriers that operate nonstop services on this route:

  • American Airlines - (AA) with 230 monthly flights
  • United Airlines - (UA) with 178 monthly flights
  • Delta Air Lines - (DL) with 139 monthly flights
  • JetBlue Airways - (B6) with 30 monthly flights

Are Logan Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
It is possible to get great last-minute deals from BOS to O'Hare Airport, but it's also possible to miss out entirely! As many airlines publish prices up to a year in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you're always getting the latest offers.

Explore a world of travel with Expedia

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