Cheap Flights from Boston to Chicago

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Compare Boston to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

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Flight deals from Boston to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Boston to Chicago? If you want to travel next month, round-trip fares start from AED 654. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.AED 325 per passenger.Departing Tue, Nov 17.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Boston Logan International on Tue, Nov 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 325, select.

Chicago.AED 326 per passenger.Departing Sat, Oct 24.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Boston Logan International on Sat, Oct 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 326, select.

Chicago.AED 327 per passenger.Departing Tue, Sep 22.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Boston Logan International on Tue, Sep 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 327, select.

Chicago.AED 360 per passenger.Departing Fri, Dec 11.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Boston Logan International on Fri, Dec 11, arriving in Chicago Midway.Price includes taxes and charges.From AED 360, select.

Chicago.AED 391 per passenger.Departing Tue, Oct 20.One-way flight with jetBlue.Outbound direct flight with jetBlue departing from Boston Logan International on Tue, Oct 20, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 391, select.

Chicago.AED 398 per passenger.Departing Sat, Dec 5.One-way flight with jetBlue.Outbound direct flight with jetBlue departing from Boston Logan International on Sat, Dec 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 398, select.

Chicago.AED 398 per passenger.Departing Mon, Mar 1.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Boston Logan International on Mon, Mar 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 398, select.

Chicago.AED 398 per passenger.Departing Mon, Sep 14.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Boston Logan International on Mon, Sep 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 398, select.

Chicago.AED 398 per passenger.Departing Wed, Nov 4.One-way flight with jetBlue.Outbound direct flight with jetBlue departing from Boston Logan International on Wed, Nov 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 398, select.

Chicago.AED 398 per passenger.Departing Mon, Jan 11.One-way flight with Delta.Outbound direct flight with Delta departing from Boston Logan International on Mon, Jan 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 398, select.

Chicago.AED 398 per passenger.Departing Thu, Feb 11.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Boston Logan International on Thu, Feb 11, arriving in Chicago Midway.Price includes taxes and charges.From AED 398, select.

Chicago.AED 448 per passenger.Departing Thu, Aug 27.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Boston Logan International on Thu, Aug 27, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 448, select.

Chicago.AED 466 per passenger.Departing Wed, Apr 7.One-way flight with jetBlue.Outbound direct flight with jetBlue departing from Boston Logan International on Wed, Apr 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 466, select.

Chicago.AED 467 per passenger.Departing Sat, May 1.One-way flight with Delta.Outbound direct flight with Delta departing from Boston Logan International on Sat, May 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 467, select.

Chicago.AED 467 per passenger.Departing Tue, Jun 8.One-way flight with Delta.Outbound direct flight with Delta departing from Boston Logan International on Tue, Jun 8, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 467, select.

Chicago.AED 468 per passenger.Departing Mon, Jul 5.One-way flight with Delta.Outbound direct flight with Delta departing from Boston Logan International on Mon, Jul 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 468, select.

Find the cheapest month to fly from Boston to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Boston to Chicago flights are currently cheapest in November.

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Direct flights from Boston to Chicago

Alternative Boston to Chicago routes

Looking for the cheapest, fastest or easiest route from Boston to Chicago? You could fly into the following airports instead.

Boston to Chicago: Flight information

The things to know before you go.

Cheapest flight found	AED 325
Cheapest month to fly	November
Average flight time	2 hrs, 53 mins
Most popular airline	American Airlines
Average flights per week	569

Finding cheap flights from Boston to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are round-trip flights from Boston to Chicago?

The best price we found for a round-trip flight from Boston to Chicago is AED 654. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Boston to Chicago?

2 hours and 52 minutes is the average flight time from Boston to Chicago.

Which airlines fly direct from Boston to Chicago?

American Airlines, Southwest Airlines and United fly direct from Boston to Chicago.

How many flights are there a week from Boston to Chicago?

There are 2,276 flights per week flying from Boston to Chicago, as of August 2026.

When is the cheapest time to fly from Boston to Chicago?

The cheapest month to fly from Boston to Chicago is usually September.

What's the cheapest airport to fly to in Chicago?

If you're flying from Boston, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the center of Chicago. We've found flights to this airport from AED 654.

Which upcoming date is cheapest to fly from Boston to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Boston to Chicago on Tuesday, September 15, 2026.

Can I get a direct flight from Boston to Chicago?

Yes – the average flight time is 2 hours and 52 minutes.

How can I get the best flight deal from Boston to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In August, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly with from Boston to Chicago?

The cheapest airline that flies to Chicago is Frontier Airlines, and the cheapest airline that flies to Chicago O'Hare International Airport is jetBlue.

How to find cheap flights from Boston to Chicago

Looking for cheap flight tickets from Boston to Chicago? Skyscanner compares flight prices across more than 1,200 airlines and travel providers.

Regardless of whether you're looking for a one-way ticket to Chicago or a return flight, here are some tips to secure the best flight price and make planning your journey as smooth as possible.

Simply hit search. From Emirates and Etihad to international carriers like Air India and Wizz Air, we compare all major airlines with the most popular online travel agents to find the cheapest plane tickets from Boston to Chicago. And with us there are no hidden fees - what you see is what you pay.

Flex your dates to find the cheapest BOSA - CHIA flight tickets on Skyscanner. Search for flights but don’t enter the departure date and instead click ‘whole month’. This tool will find the cheapest month and dates to fly to Chicago from Boston.

Set up a Price Alert for Boston-Chicago flight tickets. You can easily track the fare of flights by creating an alert. Whenever prices go down or up, you'll get an email to help make sure you get the best possible flight deal. Or download our app and get price alerts straight to your phone.

Fly without stops. Only interested in direct flights between Boston and Chicago? Make sure to tick 'Non-stop flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.

Hotels in Chicago

Looking for a hotel in Chicago? Whether you’re looking for a local hotel or a global brand, discover the best prices and exclusive rates for hotels in Chicago by comparing the biggest names in travel.

Car hire in Chicago

If you’re looking for car rental in Chicago, we can help you uncover the best car hire deals. We search hundreds of car hire companies allowing you to instantly compare prices and then book.

Book flight tickets from Boston to Chicago with extra peace of mind

Back in 2020, most airlines introduced policies to make travel during COVID-19 as easy as possible. The worst of the pandemic is now over, but some of these policies remain in place for you to take advantage of as you step back out into the world.

Find flexible getaways. Some airlines introduced flexible booking policies in 2020 – and many of these are still available. If you book a flexible plane ticket from Boston to Chicago, it means your money is still safe if your flights are changed or cancelled due to COVID-19.

Get insured. Choose travel cost protection that covers COVID-19, too. It's available at the checkout as you book your flight from Boston to Chicago with us.