Cheap Flights from Chicago to Boston Logan International

Compare Chicago to Boston Logan International flight deals

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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 foundRs15,526
Cheapest month to flyAugust
Average flight time2 hrs, 23 mins
Most popular airlineAmerican Airlines
Average flights per week693

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 Rs33,210. 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 July 2025, there are 1,386 flights per week flying from Chicago to Boston Logan International.
The cheapest month to fly from Chicago to Boston Logan International is usually August.
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 Friday, 8 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.
The cheapest airline that flies to Boston Logan International is jetBlue .

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

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

  • The average length of a direct Chicago to Logan International Airport flight is 2 hours 30 minutes.

  • Logan International Airport is located in Boston. The city operates on the UTC-4 timezone and is one hour ahead of Chicago.

  • O'Hare International Airport (ORD) to Logan International Airport (BOS) is the most popular route. There are 142 direct departures a week to pick from. If you prefer a later start to the day, take the last flight with United Airlines at 9:31pm. Go for the first ORD to BOS departure with United Airlines at 6am if you're aiming for an earlier start.

  • For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your flight from Chicago to BOS.

  • If you're flying during a bank holiday or other peak period, allow extra time. Get there two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can take a direct flight from Chicago to Logan International Airport (BOS) out of O'Hare International Airport (ORD).

  • At ORD, you'll find a good selection of airlines offering direct flights from Chicago to Logan International Airport, including:

  • United Airlines sees the most traveller bookings for flights from ORD to BOS.

  • United Airlines is the top performer for punctuality on this route.

  • ORD is around 40 kilometres from central Chicago. If you're ride-sharing, driving or catching a cab from the centre, it'll take you 35 minutes or so to get there, depending on traffic. If you're planning to take public transport, expect the journey time to be around 55 minutes.

  • Have an early flight from Chicago to Logan International Airport? Avoid the stress of rushing to the terminal (and get some bonus sleep) by staying at one of these hotels near O'Hare International Airport:

  • Of the departures from O'Hare International Airport, 74.85% land on time at their destination.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • You can book a direct Chicago to Logan International Airport (BOS) flight ticket with departures from Chicago Midway International Airport (MDW). Work out whether leaving from MDW works best for your plans.

  • Southwest Airlines offers direct flights from Chicago to BOS departing from MDW. Book your favourite seat and get to your destination in a single journey.

  • Southwest Airlines ranks number one in bookings on the MDW to BOS route.

  • The most punctual carrier is Southwest Airlines. Its Chicago Midway International Airport to Logan International Airport flights land without delay 72.99% of the time.

  • MDW is around 19 kilometres from central Chicago. It'll take 20 minutes or so to get to the airport in a car from the city centre. Public transport takes roughly 45 minutes.

  • Want to treat yourself to an extra night away before your Chicago to BOS flight? Unwind in a hotel near Chicago Midway International Airport before your break officially begins. These stays are expecting you:

  • 77.88% of flights taking off from Chicago Midway International Airport arrive within the expected time frame.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kilometres from central Chicago. Driving from the city centre to the airport takes about 1 hour 25 minutes. If you're planning to take public transport, expect a journey time of around 4 hours 15 minutes.

  • Sleep a little longer, move a little slower, and still make your Chicago to Logan International Airport flight with time to spare. These hotels near Chicago Rockford International Airport make departure day effortless if you're setting off early:

  • Airports have an on-time performance rating that measures how often flights touch down when they should. At RFD, that figure is 76.19%.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Logan International Airport (BOS)

Getting from Logan International Airport (BOS) to central Boston

  • Logan International Airport to the centre of Boston is about 3 kilometres. If you're renting a car or getting a cab, do some research to make your trip as easy as possible. Journey times may vary depending on the time of day and traffic conditions.

  • It takes around 25 minutes to get there using public transport.

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

  • Rs15,526 is the lowest price for a one-way ticket from Chicago to Logan International Airport. A return flight starts from Rs33,210. These fares can change based on demand and availability.

  • Score cheap flights from Chicago to BOS by booking one month ahead. Based on our research, that's the ideal time frame for finding a bargain.

  • June is when you're most likely to land a good deal on a Chicago to Logan International Airport ticket. If you'd like to travel during a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Be the first to know about deals for flight tickets from Chicago to BOS by creating a Price Alert. We'll send you an email or notification on the app when a lower fare becomes available.

  • Bag the best deal on a flight from Chicago to Logan International Airport with the help of the filters. Pick your ideal departure and arrival times, airlines and number of stops. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best.'

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

  • May is the quietest month for flights from Chicago to Logan International Airport (BOS), while August is the most popular. Pick the ideal time to visit Boston based on whether you like a lively atmosphere or a more laid-back vibe.

  • Book a Chicago to BOS flight ticket departing in July if you want to experience the city during its warmest month. You can expect temperatures in Boston to range from 16ºC to 29ºC.

  • January has temperatures of between -8ºC and 6ºC. Look for cheap tickets from Chicago to Logan International Airport around that time if you like travelling in cooler conditions.

More about Boston

  • When it comes to looking for somewhere to rest your head, you'll find the best stays in Boston right here. Explore these options after you've booked your flight from Chicago to Logan International Airport:

  • Your Boston visit should come with a side of sightseeing. Big-name attractions you won't want to miss include Museum of Fine Arts Boston, Freedom Trail and Quincy Market.

Explore more of the United States

  • Boston is easy to fall in love with, but there are so many other parts of the United States you should also see. Around 290 kilometres south-west of Boston, a visit to Yonkers will fill your itinerary to the brim. Check out popular attractions like LEGOLAND Discovery Centre Westchester, Unity Park and Philipse Manor Hall.

  • Springfield is another standout destination in the United States and is around 137 kilometres west of Boston. No trip is complete without a visit to Titanic Museum, Basketball Hall of Fame and Springfield Museums.

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