CA $75 Cheap Flights from Boston (BOS) to Chicago (CHI)

View CA $75 flight on Thu, Oct. 23, 2025Opens in a new window

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

Prices were available within the past 7 days and start at CA $75 for one-way flights and CA $161 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue., Jun. 10 - Tue., Jun. 17
BOS
Boston
ORD
Chicago
CA $161 Roundtrip, found 4 hours ago
CA $161
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue., Jun. 10 from Boston to Chicago, returning Tue., Jun. 17, priced at CA $161 found 4 hours ago
American Airlines
Tue., Jun. 10 - Tue., Jun. 17
BOS
Boston
ORD
Chicago
CA $162 Roundtrip, found 4 hours ago
CA $162
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue., Jun. 10 from Boston to Chicago, returning Tue., Jun. 17, priced at CA $162 found 4 hours ago
Delta
Tue., Apr. 29 - Sat., May 3
BOS
Boston
ORD
Chicago
CA $162 Roundtrip, found 3 days ago
CA $162
Roundtrip
found 3 days ago
Select Delta flight, departing Tue., Apr. 29 from Boston to Chicago, returning Sat., May 3, priced at CA $162 found 3 days ago
JetBlue Airways
Thu., Jun. 5 - Wed., Jun. 11
BOS
Boston
ORD
Chicago
CA $163 Roundtrip, found 1 day ago
CA $163
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu., Jun. 5 from Boston to Chicago, returning Wed., Jun. 11, priced at CA $163 found 1 day ago
JetBlue Airways
Tue., Jun. 10 - Tue., Jun. 17
BOS
Boston
ORD
Chicago
CA $165 Roundtrip, found 4 hours ago
CA $165
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue., Jun. 10 from Boston to Chicago, returning Tue., Jun. 17, priced at CA $165 found 4 hours ago
JetBlue Airways
Thu., Jun. 5 - Wed., Jun. 11
BOS
Boston
ORD
Chicago
CA $166 Roundtrip, found 1 day ago
CA $166
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu., Jun. 5 from Boston to Chicago, returning Wed., Jun. 11, priced at CA $166 found 1 day ago
Spirit Airlines
Tue., Jun. 10 - Tue., Jun. 17
BOS
Boston
ORD
Chicago
CA $167 Roundtrip, found 4 hours ago
CA $167
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue., Jun. 10 from Boston to Chicago, returning Tue., Jun. 17, priced at CA $167 found 4 hours ago
Spirit Airlines
Fri., May 9 - Tue., May 13
BOS
Boston
ORD
Chicago
CA $180 Roundtrip, found 14 hours ago
CA $180
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Fri., May 9 from Boston to Chicago, returning Tue., May 13, priced at CA $180 found 14 hours ago
Spirit Airlines
Fri., Apr. 25 - Mon., May 5
BOS
Boston
ORD
Chicago
CA $180 Roundtrip, found 1 day ago
CA $180
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri., Apr. 25 from Boston to Chicago, returning Mon., May 5, priced at CA $180 found 1 day ago
American Airlines
Sun., May 11 - Wed., May 14
BOS
Boston
ORD
Chicago
CA $201 Roundtrip, found 4 hours ago
CA $201
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sun., May 11 from Boston to Chicago, returning Wed., May 14, priced at CA $201 found 4 hours ago
Flight from Boston to Chicago (BOS - ORD) route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Roundtrip price
CA $154
Distance
1381 km

Boston to Illinois Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Boston to Illinois with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from BOS to CHI and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Boston to Illinois on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from BOS to CHI. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Illinois flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

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 CA $161. 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 kilometers. 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 nearby Airports

Chicago

Boston to O'Hare Intl.
CA $153.80
Boston to Midway Intl.
CA $436.70

Milwaukee

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Providence

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