RM280 Cheap Flights from Boston (BOS) to Chicago (ORD)

View RM280 flight on Sat, 31 Jan 2026Opens in a new window

Popular airlines from Boston to Chicago, IL (ORD-O'Hare Intl.)

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Cheap Flights from Boston to Chicago (BOS-ORD)

Prices were available within the past 7 days and start at RM280 for one-way flights and RM559 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 31 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM559 Return, found 2 days ago
RM559
Return
found 2 days ago
Select Delta flight, departing Sat, 31 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM559 found 2 days ago
Delta
Fri, 30 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM681 Return, found 2 days ago
RM681
Return
found 2 days ago
Select Delta flight, departing Fri, 30 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM681 found 2 days ago
United
Fri, 30 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM698 Return, found 2 days ago
RM698
Return
found 2 days ago
Select United flight, departing Fri, 30 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM698 found 2 days ago
Delta
Sat, 31 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM783 Return, found 2 days ago
RM783
Return
found 2 days ago
Select Delta flight, departing Sat, 31 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM783 found 2 days ago
Delta
Sat, 31 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM803 Return, found 2 days ago
RM803
Return
found 2 days ago
Select Delta flight, departing Sat, 31 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM803 found 2 days ago
Delta
Sat, 31 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM804 Return, found 2 days ago
RM804
Return
found 2 days ago
Select Delta flight, departing Sat, 31 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM804 found 2 days ago
Delta
Fri, 30 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM820 Return, found 2 days ago
RM820
Return
found 2 days ago
Select Delta flight, departing Fri, 30 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM820 found 2 days ago
American Airlines
Fri, 30 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM824 Return, found 2 days ago
RM824
Return
found 2 days ago
Select American Airlines flight, departing Fri, 30 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM824 found 2 days ago
American Airlines
Sat, 31 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM836 Return, found 2 days ago
RM836
Return
found 2 days ago
Select American Airlines flight, departing Sat, 31 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM836 found 2 days ago
United
Fri, 30 Jan - Sun, 1 Feb
BOS
Boston
ORD
Chicago
RM836 Return, found 2 days ago
RM836
Return
found 2 days ago
Select United flight, departing Fri, 30 Jan from Boston to Chicago, returning Sun, 1 Feb, priced at RM836 found 2 days ago
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
RM559
Distance
1381 km
Average flight time
2 hours 4 mins

Perfect flights from Boston to Chicago

Your Journey from Boston to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Boston to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. Our selection of flights from Logan Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Boston to Chicago Flights

Experience the joy of finding cheap flights from Logan Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from RM280 and roundtrip prices from RM559*.
 

Pre-Flight Essentials

Ensure a smooth journey from Boston to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Boston to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Boston to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Boston to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Boston to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

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 RM559. 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

*Available to Expedia members.