Cheap Flights from Boston Logan International to Chicago

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Flight deals from Boston Logan International to Chicago

Looking for a cheap last-minute deal or the best return flight from Boston Logan International to Chicago? Find the lowest prices on one-way and return tickets right here.

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Find the cheapest month to fly from Boston Logan International to Chicago

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

Direct flights from Boston Logan International to Chicago

Alternative Boston Logan International to Chicago routes

Looking for the cheapest, fastest or easiest route from Boston Logan International 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£49
Cheapest month to flyJune
Average flight time2 hrs, 48 mins
Most popular airlineAmerican Airlines
Average flights per week715

Finding cheap flights from Boston Logan International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Boston Logan International to Chicago is £49. 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.
2 hours and 48 minutes is the average flight time from Boston Logan International to Chicago.
American Airlines, Southwest Airlines and United fly direct from Boston Logan International to Chicago.
As of May 2024, there are 715 flights per week flying from Boston Logan International to Chicago.
The cheapest month to fly from Boston Logan International to Chicago is usually June.
If you're flying from Boston Logan International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the centre of Chicago. We've found flights into this airport from £49.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Boston Logan International Airport to Chicago on Tuesday, 11 June 2024.
Yes – the average flight time is 2 hours and 48 minutes.
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.
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.
In May, the average temperature is usually around 13°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.
Currently, Spirit Airlines offers the cheapest flight tickets to Chicago.

This information is correct as of August 2016

Airlines that fly from Boston to Chicago

American Airlines, JetBlue Airways, Spirit Airlines, United Airlines and United Express all fly from Boston Logan Airport to Chicago O'Hare. This is the airport's busiest domestic route so we recommend booking your tickets as far in advance as possible.

Southwest Airlines also fly from Boston Logan to a smaller airport, Chicago Midway.

Terminal Information – Departing

This is only a guideline. Always check your boarding pass for up-to-date terminal information.

Boston Logan International Airport has four terminals. Check your boarding card or flight booking information to find out which one your flight to Chicago departs from. Free Wi-Fi (from Boingo) is available throughout the airport. There are plenty of places to grab a bite to eat, serving international cuisine as well as traditional American snacks. Terminals A, B and C all have Kidport playgrounds so that little ones can run off some energy before boarding their flight. The airport is also involved in a community art programme, so look out for exciting works by local artists.

Terminal Information – Arriving

Some hotels in Chicago offer free shuttle transportation from the airport. We recommend checking this out while booking. If your hotel doesn't offer a shuttle, don't worry. It's easy to get into the city centre from both airports.

At Chicago Midway: Expect to pay about $30* for a taxi to the city centre. Alternatively you can take the CTA train for $2.25*. Car hire at Chicago Midway Airport is also available.

At Chicago O'Hare: taxis to the city centre cost about $40*. The CTA train also runs from this airport to the city, and costs $2.25*. If you're planning to drive, remember to compare car hire from Chicago O'Hare Airport.

Practical Information

British citizens visiting the USA will need to show their passports before boarding. American citizens can use their driving licenses. Try to arrive at Boston Airport at least 90 minutes before boarding your flight.

What to expect in Chicago

Chicago is one hour behind Boston. Winters in Chicago are a lot colder, with an average temperature of -6°C in January. This is colder than the average low of -5°C in Boston. Average lows in Chicago sit around -11°C with highs of -1°C, so you'll definitely want to pack your thermals. Summer in Chicago is warm and pleasant, with average temperatures of 21-23°C from June to August. Highs of 27-29°C are quite common during these months. Prices in both cities are quite similar, and you probably won't notice any difference on day-to-day activities.

Looking for travel inspiration? Check out these 10 great things to do in Chicago.

*Prices subject to change


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.