Cheap Flights from Boston Logan International to Chicago

Compare Boston Logan International 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 from Boston Logan International to Chicago

Looking for a cheap last-minute deal or the best return flight from Boston Logan International Airport to Chicago? If you want to travel next month, return fares start from Rs51,849. Find the lowest prices on one-way and return tickets right here.

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 August.

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 foundRs19,475
Cheapest month to flyAugust
Average flight time2 hrs, 53 mins
Most popular airlineAmerican Airlines
Average flights per week1,488

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 Rs41,052. 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 53 minutes is the average flight time from Boston Logan International to Chicago.
American Airlines, Southwest Airlines and Republic Airways fly direct from Boston Logan International to Chicago.
As of June 2026, there are 1,488 flights per week flying from Boston Logan International to Chicago.
The cheapest month to fly from Boston Logan International to Chicago is usually August.
If you're flying from Boston Logan International Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from Rs41,052.
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 Wednesday, 26 August 2026.
Yes – the average flight time is 2 hours and 53 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 June, the average temperature is usually around 19°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, Southwest Airlines offers the cheapest flight tickets to Chicago.

Flying from Boston Logan International Airport (BOS) to Chicago: what you need to know

  • Expect to be travelling for 2 hours 25 minutes. On average, that's the time it takes for a direct flight from Boston Logan International Airport to Chicago.

  • Boston Logan International Airport is located in Boston. Following the UTC-6 timezone, Chicago is one hour behind Boston.

  • The most popular route is from Boston Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD). You can choose from 147 weekly services between these two airports. If you'd like to get on your way as soon as possible, the earliest flight from BOS to ORD is the 05:00 American Airlines service. If you'd rather travel later, the last departure is at 21:31 with United Airlines.

  • For hassle-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to board your BOS to Chicago flight.

  • During popular months such as July, it's a good idea to get to the airport earlier than usual. Arrive two hours before domestic departures and four hours ahead of an international flight when you travel during peak periods in general.

  • You can book a direct Boston Logan International Airport to Chicago ticket. Start your trip at BOS and arrive at Chicago O'Hare International Airport (ORD).

  • A variety of airlines offer direct flights from Boston Logan International Airport to Chicago. The most popular include:

  • Located around 3 kilometres from the centre of Boston, BOS can be reached in about 20 minutes by car, depending on traffic. The journey on public transport takes roughly 25 minutes.

  • Booked an early flight from Boston Logan International Airport to Chicago? Avoid the hassle of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels near BOS:

  • 75% of flights departing from Boston Logan International Airport land at their destination on time.

  • You'll find BOS at One Harborside Drive.

How to find the cheapest flights from Boston Logan International Airport (BOS) to Chicago

  • The best price we've seen for a one-way Boston Logan International Airport to Chicago flight is Rs19,475. The cheapest price for a return flight is Rs41,052. Keep in mind fares can change due to demand at the time of booking.

  • Get cheap flights from BOS to Chicago by booking one month ahead. Based on our research, that's the sweet spot for bagging a bargain.

  • June is the best month for landing an amazing deal on Boston Logan International Airport to Chicago tickets. If you're looking to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for every month.

  • Snapping up a cheap flight from BOS to Chicago is a breeze with Price Alerts. Simply set up one of these automatic notifications and we'll notify you when a new discount appears.

  • Tailor your trip with filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Fastest' or 'Best' flights from Boston Logan International Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometres. It'll take you about 30 minutes to reach the centre driving.

  • If you're travelling on public transport, expect a journey time of around 45 minutes.

  • Consider staying in a hotel close to ORD if you're coming in on a late flight from Boston Logan International Airport to Chicago. Check in to one of these options and make your first night all about catching up on rest:

  • Get the best deal by reserving your vehicle from Chicago O'Hare International Airport around four weeks before your flight from BOS to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 16 kilometres from central Chicago. After your flight from Boston Logan International Airport to Chicago, it'll take you around 25 minutes to reach the heart of the city in a taxi or ride-share.

  • If you travel by public transport, you'll reach the centre in 30 minutes or so.

  • You'll find some comfortable places to rest your head close to MDW. Kick back and get cosy after your BOS to Chicago flight at one of these well-located options:

  • Lock in the lowest price by securing your ride from MDW four weeks ahead of time. You'll also have access to a wider selection of vehicles.

  • Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 145 kilometres from central Chicago. It takes about 1 hour 40 minutes to reach the city centre in a taxi or ride-share after your flight from Boston Logan International Airport to Chicago.

  • Public transport will take you there in roughly 2 hours.

  • Reserve a hotel close to RFD and get from baggage claim to your bed in a snap. Whether you're coming in on a late BOS to Chicago flight or just want to keep your travel plans simple, these accommodation options offer convenience when you need it most:

  • Booking a couple of weeks in advance of your flight from Boston Logan International Airport to Chicago is a smart move. As well as better deals, you'll have a wider selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • It's time to choose your dates for your flight from Boston Logan International Airport to Chicago. July is the busiest month for a trip to Chicago. If you like a more relaxed vibe, go in January.

  • When booking your Boston Logan International Airport to Chicago plane ticket, think about what kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.

  • If you like travelling in cooler conditions, look for a cheap ticket from BOS to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the best stays in Chicago right here. Check out these hotels as soon as you've locked in your flight from Boston Logan International Airport to Chicago:

  • There are so many things to see and do in this city it can be tricky to work out where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are top attractions which should be on any well-planned Chicago itinerary.

Explore more of the United States

  • Chicago has its own special appeal, but there are so many other corners of the United States waiting to be discovered. About 451 kilometres southeast of Chicago, a trip to Columbus will keep you busy. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another standout destination in the United States and is around 257 kilometres southeast of Chicago. No trip is complete without seeing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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