Cheap Flights from Chicago to Boston Logan International

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Flight deals from Chicago to Boston Logan International

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

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

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

Direct flights from Chicago to Boston Logan International

Chicago to Boston Logan International: Alternative routes

Compare routes from Chicago to Boston below. You may find an airport to fly into that's cheaper, faster, or easier than Boston Logan International.

Chicago to Boston: Flight information

The things to know before you go.
Cheapest flight found80 €
Cheapest month to flyAugust
Average flight time2 hrs, 23 mins
Most popular airlineAmerican Airlines
Average flights per week594

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

The best price we found for a return flight from Chicago to Boston Logan International is 80 €. 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 23 minutes is the average flight time from Chicago to Boston Logan International.
American Airlines, Qatar Airways and Alaska Airlines fly direct from Chicago to Boston Logan International.
As of March 2025, there are 603 flights per week flying from Chicago to Boston Logan International.
The cheapest month to fly from Chicago to Boston Logan International is usually March 2025.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Boston Logan International Airport on Wednesday, 20 August 2025.
Yes – the average flight time is 2 hours and 23 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 Boston Logan International 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 Boston is around 40 days in advance, so don’t leave your flight to the last minute.

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

  • Begin your trip planning by checking out the most convenient departure point for your flight from Chicago to Logan International Airport (BOS). Explore the options for departing from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.

  • Approximately 2 hours 26 minutes is how long you can expect to be in the air on a direct flight from Chicago to Logan International Airport.

  • The timezone in Boston is UTC-4, which is 1 hour ahead of Chicago. Logan International Airport is located in Boston.

  • O'Hare International Airport (ORD) to Logan International Airport (BOS) is the most popular route. There are 193 direct weekly flights to choose from. If you prefer starting your day later, hop on the last flight with Spirit Airlines at 22:14. Go for the first ORD to BOS departure operated by Southwest Airlines at 05:00 if you want to get going earlier.

  • Get to the airport on time so you don't miss your flight from Chicago to BOS. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid the stress of rushing.

  • Flying during a peak month like August? Popular seasons (like spring break, summer and New Year) can add another hour at check-in and security. Play things extra safe and arrive up to four hours ahead of an international flight and two hours before a domestic departure.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is a convenient option for travelling directly to your destination. Nonstop flights from Chicago to Logan International Airport (BOS) depart from this terminal.

  • A range of airlines at ORD operate direct flights from Chicago to Logan International Airport. The most well-known include:

  • The distance from central Chicago to ORD is around 40 kilometres. Check out Google Maps for the quickest way to get there, whether you plan to drive or take public transport.

  • Want a leisurely start to your trip? Stay near O'Hare International Airport. Whether you've booked an early flight from Chicago to Logan International Airport or just don't like being rushed, these hotels are perfect:

Chicago Midway International Airport (MDW)

About Logan International Airport (BOS)

Getting from Logan International Airport (BOS) to central Boston

  • Logan International Airport to the centre of Boston takes about 12 minutes by car. It's approximately 5 kilometres away. Discover what options are available, such as car rentals, cabs or ride-sharing.

  • If you're travelling by public transport, expect a journey time of about 23 minutes.

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

  • 44 € is the lowest price we've found for a one-way ticket from Chicago to Logan International Airport. Return flights start from 80 €. Prices may vary depending on availability at the time of booking.

  • Score cheap tickets from Chicago to BOS by booking 9 months ahead. According to flight price data, that's the sweet spot for bagging a bargain.

  • The cheapest month for tickets from Chicago to Logan International Airport is June. Use the 'Whole month' tool to find the most affordable day to fly if you're flexible with your plans.

  • Set up a Price Alert for cheap tickets from Chicago to BOS. You don't need to check back in every day to find out if fares have dropped. We'll tell you the moment there's a change in price.

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

The best time to fly from Chicago to Logan International Airport (BOS)

  • August is the busiest month to board a flight from Chicago to Logan International Airport while May is the quietest. To work out the ideal time to visit Boston, consider whether you like a lively atmosphere or a quieter vibe.

  • Lock in your flight from Chicago to BOS for July if you're eager to head to the city during its warmest month. Expect temperatures in Boston to range from 16ºC to 29ºC.

  • If you want cooler conditions, look for a cheap flight from Chicago to Logan International Airport in January when temperatures average between -8ºC and 6ºC.

More about Boston

  • Start your Boston trip off on the right foot by choosing the ideal place to stay. Once you've booked your flight from Chicago to Logan International Airport, check out our range of accommodation options including:

  • There are so many things to explore in this city it can be hard to know where to begin. Freedom Trail, Museum of Fine Arts Boston and Boston Tea Party Ships & Museum are top sights which should feature on every Boston itinerary.

Complete your Boston trip with a car rental

  • We use the same magic that helped you find your cheap flight from Chicago to Logan International Airport to track down your perfect ride. Check out our car rentals in Boston and compare your options in one place. Plus we give you all the info you need to know, from the most popular car type to the best time to book.

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