£51 Cheap Flights from Boston to Chicago (BOS to CHI)

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

Prices were available within the past 7 days and start at £51 for one-way flights and £102 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

All deals

One way

Return

Tue, 21 May - Wed, 29 May

BOS

Boston

ORD

Chicago

£102

Return

found 1 day ago

Wed, 22 May - Sat, 25 May

BOS

Boston

ORD

Chicago

£106

Return

found 1 day ago

Tue, 16 Jul - Wed, 24 Jul

BOS

Boston

ORD

Chicago

£110

Return

found 6 days ago

Wed, 10 Jul - Wed, 17 Jul

BOS

Boston

ORD

Chicago

£118

Return

found 6 days ago

Wed, 17 Jul - Wed, 24 Jul

BOS

Boston

ORD

Chicago

£130

Return

found 6 days ago

Wed, 29 May - Sat, 1 Jun

BOS

Boston

ORD

Chicago

£138

Return

found 5 days ago

Wed, 17 Jul - Wed, 24 Jul

BOS

Boston

ORD

Chicago

£139

Return

found 6 days ago

Wed, 12 Jun - Thu, 13 Jun

BOS

Boston

ORD

Chicago

£139

Return

found 5 days ago

Sat, 18 May - Sat, 25 May

BOS

Boston

ORD

Chicago

£140

Return

found 1 day ago

Wed, 12 Jun - Thu, 13 Jun

BOS

Boston

ORD

Chicago

£143

Return

found 5 days ago

Flight from Boston to Chicago route information
Origin airport	Logan Intl.
Destination airport	O'Hare Intl.
Return price	£102
Distance	1381 km

Compare flights from Boston to Chicago easily and book in confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Boston to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to CHI-All Airports in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Logan Intl. to CHI-All Airports.

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.

Grab a great deal on your flight from Logan Intl. (BOS) to CHI-All Airports (CHI)

The easiest way to view the best deals on flights from Boston to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Logan Intl. to CHI-All Airports start at just £102 and range up to £143.

To find an even better deal, try

being flexible on your dates – midweek flights can be cheaper
looking for other airports near Boston and Chicago
booking your flight during May, the cheapest month on this route
varying your flight times – early morning and late at night are sometimes cheaper

Why you should book your Boston to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Logan Intl. to CHI-All Airports for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.

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 £102. 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.