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

View AU$106 flight on Tue, 4 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 for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, 11 Sept - Mon, 15 Sept
BOS
Boston
ORD
Chicago
AU$195 Return, found 4 days ago
AU$195
Return
found 4 days ago
Select American Airlines flight, departing Thu, 11 Sept from Boston to Chicago, returning Mon, 15 Sept, priced at AU$195 found 4 days ago
American Airlines
Mon, 10 Nov - Fri, 14 Nov
BOS
Boston
ORD
Chicago
AU$203 Return, found 6 days ago
AU$203
Return
found 6 days ago
Select American Airlines flight, departing Mon, 10 Nov from Boston to Chicago, returning Fri, 14 Nov, priced at AU$203 found 6 days ago
Delta
Mon, 10 Nov - Fri, 14 Nov
BOS
Boston
ORD
Chicago
AU$218 Return, found 6 days ago
AU$218
Return
found 6 days ago
Select Delta flight, departing Mon, 10 Nov from Boston to Chicago, returning Fri, 14 Nov, priced at AU$218 found 6 days ago
American Airlines
Thu, 11 Sept - Mon, 15 Sept
BOS
Boston
ORD
Chicago
AU$233 Return, found 4 days ago
AU$233
Return
found 4 days ago
Select American Airlines flight, departing Thu, 11 Sept from Boston to Chicago, returning Mon, 15 Sept, priced at AU$233 found 4 days ago
Delta
Sat, 18 Oct - Sat, 25 Oct
BOS
Boston
ORD
Chicago
AU$242 Return, found 2 days ago
AU$242
Return
found 2 days ago
Select Delta flight, departing Sat, 18 Oct from Boston to Chicago, returning Sat, 25 Oct, priced at AU$242 found 2 days ago
American Airlines
Thu, 11 Sept - Mon, 15 Sept
BOS
Boston
ORD
Chicago
AU$256 Return, found 4 days ago
AU$256
Return
found 4 days ago
Select American Airlines flight, departing Thu, 11 Sept from Boston to Chicago, returning Mon, 15 Sept, priced at AU$256 found 4 days ago
American Airlines
Mon, 10 Nov - Fri, 14 Nov
BOS
Boston
ORD
Chicago
AU$257 Return, found 6 days ago
AU$257
Return
found 6 days ago
Select American Airlines flight, departing Mon, 10 Nov from Boston to Chicago, returning Fri, 14 Nov, priced at AU$257 found 6 days ago
United
Thu, 11 Sept - Mon, 15 Sept
BOS
Boston
ORD
Chicago
AU$302 Return, found 4 days ago
AU$302
Return
found 4 days ago
Select United flight, departing Thu, 11 Sept from Boston to Chicago, returning Mon, 15 Sept, priced at AU$302 found 4 days ago
JetBlue Airways
Tue, 7 Oct - Fri, 10 Oct
BOS
Boston
ORD
Chicago
AU$357 Return, found 4 days ago
AU$357
Return
found 4 days ago
Select JetBlue Airways flight, departing Tue, 7 Oct from Boston to Chicago, returning Fri, 10 Oct, priced at AU$357 found 4 days ago
Alaska Airlines
Sat, 18 Oct - Sat, 25 Oct
BOS
Boston
ORD
Chicago
AU$1,019 Return, found 2 days ago
AU$1,019
Return
found 2 days ago
Select Alaska Airlines flight, departing Sat, 18 Oct from Boston to Chicago, returning Sat, 25 Oct, priced at AU$1,019 found 2 days ago

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

November is typically the cheapest month to fly

From AU$120 - AU$414 per traveller.
Flight from Boston to Chicago route information
Origin airport
Logan Intl.
Destination airport
O'Hare Intl.
Return price
AU$194
Distance
1381 km

Your quick guide to flights from Boston to Chicago

Pick up great flights from Boston to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Boston to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Boston to Chicago that take around hours.

Find cheap flights from Boston to Chicago

From the great flight deals with prices currently ranging from AU$195 to AU$1,019, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Boston to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in September.

Reasons to book your flight from Boston to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Boston to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

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 AU$195. 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 Flight Deals

Chicago

Boston to O'Hare Intl.
AU$194.30

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