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

Flight deals Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Boston to Chicago

Looking for a cheap last-minute deal or the best return flight from Boston to Chicago? If you want to travel next month, return fares start from P12,385. Find the lowest prices on one-way and return tickets right here.

Chicago.P5,704 per passenger.Departing Tue, 10 Nov.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Tue, 10 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From P5,704, select.

Chicago.P6,147 per passenger.Departing Thu, 10 Dec.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Thu, 10 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From P6,147, select.

Chicago.P6,325 per passenger.Departing Mon, 1 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Boston Logan International on Mon, 1 Mar, arriving in Chicago Midway.Price includes taxes and charges.From P6,325, select.

Chicago.P6,342 per passenger.Departing Wed, 10 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Boston Logan International on Wed, 10 Feb, arriving in Chicago Midway.Price includes taxes and charges.From P6,342, select.

Chicago.P6,514 per passenger.Departing Mon, 4 Jan.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Mon, 4 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From P6,514, select.

Chicago.P7,109 per passenger.Departing Sat, 31 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Boston Logan International on Sat, 31 Oct, arriving in Chicago Midway.Price includes taxes and charges.From P7,109, select.

Chicago.P8,030 per passenger.Departing Sat, 17 Oct.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Sat, 17 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From P8,030, select.

Chicago.P9,898 per passenger.Departing Sat, 24 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Boston Logan International on Sat, 24 Jul, arriving in Chicago Midway.Price includes taxes and charges.From P9,898, select.

Chicago.P9,911 per passenger.Departing Sat, 1 May.One-way flight with jetBlue.Outbound direct flight with jetBlue departs from Boston Logan International on Sat, 1 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,911, select.

Chicago.P9,940 per passenger.Departing Sat, 3 Apr.One-way flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Sat, 3 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,940, select.

Chicago.P9,940 per passenger.Departing Fri, 25 Jun.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Boston Logan International on Fri, 25 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,940, select.

Chicago.P9,942 per passenger.Departing Sun, 1 Aug.One-way flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Sun, 1 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,942, select.

Chicago.P10,531 per passenger.Departing Sat, 4 Sep.One-way flight with Delta.Outbound direct flight with Delta departs from Boston Logan International on Sat, 4 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From P10,531, 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	P5,704
Cheapest month to fly	November
Average flight time	2 hrs, 55 mins
Most popular airline	American Airlines
Average flights per week	550

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 return flights from Boston to Chicago?

The best price we found for a return flight from Boston to Chicago is P12,385. 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 55 minutes is the average flight time from Boston to Chicago.

Which airlines fly direct from Boston to Chicago?

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

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

As of October 2026, there are 550 flights per week flying from Boston to Chicago.

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

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

Which is the cheapest airport to fly into 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 centre of Chicago. We've found flights into this airport from P12,385.

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 Saturday, 7 November 2026.

Can I get a direct flight from Boston to Chicago?

Yes – the average flight time is 2 hours and 55 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 October, the average temperature is usually around 14°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.

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

The cheapest airline that flies to Chicago is jetBlue .

How to find cheap plane tickets from Boston to Chicago

Looking for cheap flights from Boston to Chicago? Whether you are aiming to find one-way or return flights, here are a few tips on how to secure the best ticket price and make your journey as smooth as possible.

Simply hit 'search'. We've compared tickets from all major online travel agents and airlines flying from Boston-Chicago to find the cheapest flights. And with us there are no hidden extras - what you see is what you pay.

Flex your dates to find the flight price for your Boston-Chicago flight. If your travel dates are flexible, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Boston.

Set up a Price Alert. You can easily track the price of your flight from Boston to Chicago by creating an alert. Whenever prices go down or up, you'll get a push notification or e-mail to help you get the best flight deal.

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

Include nearby airports in your search. Widen your search for Boston to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save on your next trip.

Find the cheapest Business class flights from Boston to Chicago. Check the difference in price of your Boston-Chicago air ticket when travelling in Economy, Premium economy, Business or First class. Note that not all cabin classes are available on every route or airline.

Search for cheap flights when out and about. To get the best flight booking experience regardless of where you are, download our app and search for flight tickets from Boston to Chicago on the go.

Book flight tickets from Boston to Chicago with peace of mind

Find flexible flights. Your airline might be offering flexible tickets from Boston to Chicago , which means you won't lose out if your flight has to be changed or cancelled.

Add travel cost protection. Avoid travel pitfalls and choose travel cost protection - it's available at the checkout as you book your Boston-Chicago flight with us.

Reduce your carbon footprint by selecting a greener flight option. To check whether there are any lower emissions flights available on the route Boston-Chicago , simply check the “only show flights with lower CO₂ emissions” box later on in your search.

Combine your cheap flight to Chicago with hotels and car hire

Once you've secured your flight booking from Boston to Chicago, we will help you discover the best prices and exclusive rates for cheap hotels in Chicago or nearby. And if you're looking for car hire, we've got you covered too. We allow you to compare hundreds of car hire companies in one search and find the best price on car rental in Chicago.

Compare Boston-Chicago tickets with other routes

Not entirely set on flying from Boston to Chicago yet? You can easily browse other destinations by searching flights to 'Everywhere' - this will allow you to find the cheapest place to travel from your chosen departure point in the Philippines or abroad.

Plan the rest of your trip from Boston to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.