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.

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 foundP5,990
Cheapest month to flyJune
Average flight time2 hrs, 50 mins
Most popular airlineAmerican Airlines
Average flights per week2,088

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 P5,990. 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 49 minutes is the average flight time from Boston Logan International to Chicago.
American Airlines, Alaska Airlines and Qatar Airways fly direct from Boston Logan International to Chicago.
As of May 2025, there are 650 flights per week flying from Boston Logan International to Chicago.
The cheapest month to fly from Boston Logan International to Chicago is usually May 2025.
If you're flying from Boston Logan International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from P5,990.
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, 3 June 2025.
Yes – the average flight time is 2 hours and 49 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.

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

  • Expect to be in the air for 2 hours 26 minutes. On average, that's the time it takes for a direct flight from Logan International Airport to Chicago.

  • The timezone in Chicago is UTC-5. The city is 1 hour behind Boston, where Logan International Airport is located.

  • The busiest route is from Logan International Airport (BOS) to O'Hare International Airport (ORD). You can choose from 194 services every week between these two airports. If you want to get on your way as soon as possible, the earliest flight from BOS to ORD is the 05:10 American Airlines service. If you prefer to leave later in the day, the final departure is at 22:06 with American Airlines.

  • To ensure you get on your flight from BOS to Chicago, leave enough time for things like baggage drop and finding your gate. Arriving two hours before international departures and an hour before domestic flights is the general rule.

  • Travelling during a peak time like August? Popular seasons (like summer, Christmas/New Year and spring break) can add another hour at check-in and security. Be extra cautious and arrive up to four hours ahead of international flights and two hours before domestic departures.

  • You can catch a direct flight from Logan International Airport to Chicago that lands at O'Hare International Airport (ORD).

  • These are some of the top airlines offering direct flights from Logan International Airport to Chicago:

  • You won't need a visa or passport to fly within United States. You will need a valid proof of identity though, like a driver's licence or an ID card. Make sure they're on your packing list once you've booked cheap tickets from Logan International Airport to Chicago.

  • Located around 5 kilometres from central Boston, BOS can be reached in about 12 minutes by car, depending on traffic. The journey on public transport will take roughly 23 minutes.

  • Want a hassle-free start to your break? Stay near BOS. Whether you're boarding an early flight from Logan International Airport to Chicago or just don't like being rushed, these hotels have you covered:

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

  • P2,613 is the lowest price we've seen for a one-way ticket from Logan International Airport to Chicago. For a return flight on this route, the best price is P5,990. Depending on when you book and the availability, these fares could change.

  • Book 10 months before you travel. After looking at the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from BOS to Chicago.

  • June is the cheapest month for tickets from Logan International Airport to Chicago. If you'd like to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for each month.

  • Finding a cheap ticket from BOS to Chicago is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch as soon as there's a better deal.

  • Use the filters to tailor your flights from Logan International Airport to Chicago. Select your preferred departure and arrival times, number of stops and airlines. Or sort your results by 'Cheapest' to find the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month for flights from Logan International Airport to Chicago. To steer clear of the crowds, plan your trip to Chicago in February when it's quieter.

  • Lock in your flight from Logan International Airport to Chicago for July to experience the city during its warmest month. Expect temperatures to range from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Look for cheap flights from BOS to Chicago sometime around then if you want to travel in cooler conditions.

More about Chicago

  • After booking your flight from Logan International Airport to Chicago, think about where you want to stay in this city. Make one of these options your base for exploring Chicago:

  • Millennium Park and Art Institute of Chicago are just a couple of the popular attractions to put on your Chicago must-do list. Keep the adventure rolling by checking out LandShark Beer Garden at Navy Pier.

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from Logan International Airport to Chicago isn't our only cool trick. Check out our car rentals in Chicago and have more freedom to explore. We search for deals from trusted car rental providers and put them all in one place. Instantly compare rates and then book with no fees.

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