S$89 Cheap Flights from Boston to Chicago

View S$89 flight on Fri, 6 Feb, 2026Opens in a new window

Popular airlines from Boston to Chicago

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Cheap Flights from Boston to Chicago (BOS-CHI)

Prices were available within the past 7 days and start at S$89 for one-way flights and S$178 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
S$178 Return, found 5 days ago
S$178
Return
found 5 days ago
Select Delta flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at S$178 found 5 days ago
Delta
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
S$241 Return, found 5 days ago
S$241
Return
found 5 days ago
Select Delta flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at S$241 found 5 days ago
American Airlines
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
S$249 Return, found 5 days ago
S$249
Return
found 5 days ago
Select American Airlines flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at S$249 found 5 days ago
American Airlines
Sat, 17 Jan - Sat, 24 Jan
BOS
Boston
ORD
Chicago
S$262 Return, found 5 days ago
S$262
Return
found 5 days ago
Select American Airlines flight, departing Sat, 17 Jan from Boston to Chicago, returning Sat, 24 Jan, priced at S$262 found 5 days ago
American Airlines
Thu, 15 Jan - Sun, 18 Jan
BOS
Boston
ORD
Chicago
S$275 Return, found 5 days ago
S$275
Return
found 5 days ago
Select American Airlines flight, departing Thu, 15 Jan from Boston to Chicago, returning Sun, 18 Jan, priced at S$275 found 5 days ago
United
Thu, 15 Jan - Sun, 18 Jan
BOS
Boston
ORD
Chicago
S$287 Return, found 5 days ago
S$287
Return
found 5 days ago
Select United flight, departing Thu, 15 Jan from Boston to Chicago, returning Sun, 18 Jan, priced at S$287 found 5 days ago
Delta
Thu, 15 Jan - Sun, 18 Jan
BOS
Boston
ORD
Chicago
S$293 Return, found 5 days ago
S$293
Return
found 5 days ago
Select Delta flight, departing Thu, 15 Jan from Boston to Chicago, returning Sun, 18 Jan, priced at S$293 found 5 days ago
Delta
Thu, 15 Jan - Sun, 18 Jan
BOS
Boston
ORD
Chicago
S$294 Return, found 5 days ago
S$294
Return
found 5 days ago
Select Delta flight, departing Thu, 15 Jan from Boston to Chicago, returning Sun, 18 Jan, priced at S$294 found 5 days ago
United
Thu, 15 Jan - Sun, 18 Jan
BOS
Boston
ORD
Chicago
S$300 Return, found 5 days ago
S$300
Return
found 5 days ago
Select United flight, departing Thu, 15 Jan from Boston to Chicago, returning Sun, 18 Jan, priced at S$300 found 5 days ago
United
Thu, 15 Jan - Sun, 18 Jan
BOS
Boston
ORD
Chicago
S$307 Return, found 5 days ago
S$307
Return
found 5 days ago
Select United flight, departing Thu, 15 Jan from Boston to Chicago, returning Sun, 18 Jan, priced at S$307 found 5 days ago

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

September is typically the cheapest month to fly

From S$108 - S$237 per traveller.
Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
S$178
Distance
1381 km

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, JetBlue Airways, United, American Airlines. Our selection of flights from Logan Intl. to CHI-All Airports 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 CHI-All Airports that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$89 and roundtrip prices from S$178*.
 

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 (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 S$178. 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

*Available to Expedia members.