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Cheap Flights from Chicago (CHIA) to Boston (BOS)

Compare Chicago to Boston Logan International flight deals

Find the cheapest month or even day of the year to fly 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 Airport? If you want to travel next month, return fares start from $260. Find the lowest prices on one-way and return tickets right here.
Boston.$218 per passenger.Departing Wed, 16 Sep, returning Wed, 23 Sep.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Wed, 16 Sep, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Wed, 23 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $218, select.
Boston.$221 per passenger.Departing Thu, 27 Aug, returning Tue, 1 Sep.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Thu, 27 Aug, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Tue, 1 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $221, select.
Boston.$225 per passenger.Departing Wed, 12 Aug, returning Fri, 14 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 12 Aug, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Fri, 14 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $225, select.
Boston.$252 per passenger.Departing Tue, 1 Sep, returning Tue, 6 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 1 Sep, arriving in Boston Logan International.Inbound direct flight with United departs from Boston Logan International on Tue, 6 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $252, select.
Boston.$256 per passenger.Departing Thu, 2 Jul, returning Mon, 31 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 2 Jul, arriving in Boston Logan International.Inbound direct flight with United departs from Boston Logan International on Mon, 31 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $256, select.
Boston.$260 per passenger.Departing Tue, 14 Jul, returning Tue, 21 Jul.Return flight with jetBlue.Outbound direct flight with jetBlue departs from Chicago O'Hare International on Tue, 14 Jul, arriving in Boston Logan International.Inbound direct flight with jetBlue departs from Boston Logan International on Tue, 21 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $260, select.
Boston.$261 per passenger.Departing Tue, 23 Jun, returning Tue, 23 Jun.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Tue, 23 Jun, arriving in Boston Logan International.Inbound direct flight with American Airlines departs from Boston Logan International on Tue, 23 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $261, select.
Boston.$274 per passenger.Departing Mon, 29 Jun, returning Wed, 1 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 29 Jun, arriving in Boston Logan International.Inbound direct flight with Southwest Airlines departs from Boston Logan International on Wed, 1 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $274, select.
Boston.$285 per passenger.Departing Wed, 25 Nov, returning Fri, 25 Dec.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Wed, 25 Nov, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Fri, 25 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $285, select.
Boston.$285 per passenger.Departing Wed, 6 Jan, returning Tue, 6 Apr.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Wed, 6 Jan, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Tue, 6 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $285, select.
Boston.$285 per passenger.Departing Tue, 1 Dec, returning Fri, 4 Dec.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Fri, 4 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $285, select.
Boston.$285 per passenger.Departing Thu, 5 Nov, returning Fri, 13 Nov.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 5 Nov, arriving in Boston Logan International.Inbound direct flight with United departs from Boston Logan International on Fri, 13 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $285, select.
Boston.$285 per passenger.Departing Fri, 15 Jan, returning Sun, 17 Jan.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Fri, 15 Jan, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Sun, 17 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $285, select.
Boston.$285 per passenger.Departing Wed, 14 Oct, returning Wed, 28 Oct.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Wed, 14 Oct, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Wed, 28 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $285, select.
Boston.$286 per passenger.Departing Wed, 28 Oct, returning Tue, 3 Nov.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Wed, 28 Oct, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Tue, 3 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $286, select.
Boston.$286 per passenger.Departing Fri, 26 Mar, returning Tue, 30 Mar.Return flight with Delta.Outbound direct flight with Delta departs from Chicago O'Hare International on Fri, 26 Mar, arriving in Boston Logan International.Inbound direct flight with Delta departs from Boston Logan International on Tue, 30 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $286, select.

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 September.
Jun
from $261
Jul
from $260
Aug
from $225
Sep
from $218
Oct
from $285
Nov
from $285
Dec
from $285
Jan
from $285
Feb
Find prices
Mar
from $286
Apr
from $286
May
Find prices

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.

Boston Logan International

5km from central Boston
ClosestCheapest
from $218
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Worcester

68km from central Boston
from $307
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Manchester

72km from central Boston
from $400
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Provincetown

76km from central Boston
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Fall River

76km from central Boston
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Providence

76km from central Boston
from $311
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Portsmouth

82km from central Boston
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Chicago to Boston: Flight information

The things to know before you go.
Cheapest flight found$218
Cheapest month to flySeptember
Average flight time2 hrs, 26 mins
Most popular airlineAmerican Airlines
Average flights per week784

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 $218. 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 26 minutes is the average flight time from Chicago to Boston Logan International.
American Airlines, United and Qatar Airways fly direct from Chicago to Boston Logan International.
As of June 2026, there are 784 flights per week flying from Chicago to Boston Logan International.
The cheapest month to fly from Chicago to Boston Logan International is usually September.
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, 16 September 2026.
Yes – the average flight time is 2 hours and 26 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.
The cheapest airline that flies to Boston Logan International is Delta .

Flying from Chicago to Boston 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 Boston Logan International Airport (BOS). Explore the options for setting off from Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.

  • The average time for a direct Chicago to Boston Logan International Airport flight is 2 hours 25 minutes.

  • The timezone in Boston is UTC-5, which is one hour ahead of Chicago. Boston Logan International Airport is located in Boston.

  • Chicago O'Hare International Airport (ORD) to Boston Logan International Airport (BOS) is the most popular route. There are 147 direct weekly departures to pick from. If you prefer starting your day later, take the last flight with United Airlines at 9:31pm. Choose the first ORD to BOS departure with United Airlines at 6am if you'd rather not wait around.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This will give you plenty of time to board your flight from Chicago to BOS.

  • With more travellers during peak months like July, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will help you stay ahead of the crowds. Remember things also get busy during major holidays like Christmas and local events or festivals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

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

  • At ORD, there's a good selection of airlines that offer direct flights from Chicago to Boston Logan International Airport, including:

  • The most frequently booked airline between ORD and BOS is American Airlines.

  • United is the leading carrier for punctuality on this route.

  • ORD is around 27 kilometres from central Chicago. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 30 minutes or so to get there, depending on traffic. If you're taking public transport, expect the journey time to be around 45 minutes.

  • Searching for a comfortable hotel near Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Boston Logan International Airport, these accommodation options will put you moments from your departure lounge:

  • 70% of flights that take off from Chicago O'Hare International Airport reach their destination on schedule.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Prefer to leave from Chicago Midway International Airport (MDW)? Direct Chicago to Boston Logan International Airport (BOS) plane tickets can be booked from this popular hub.

  • Southwest Airlines has direct flights from Chicago to BOS out of MDW. Book your favourite window (or aisle) seat and get to your destination in one go.

  • Southwest Airlines attracts the most bookings on the MDW to BOS route.

  • Southwest Airlines is the most punctual carrier flying from Chicago Midway International Airport to Boston Logan International Airport, with 70.46% of its services landing on time.

  • MDW is about 16 kilometres from central Chicago. It'll take 25 minutes or so to get to the airport driving from the city centre. Public transport takes approximately 30 minutes.

  • Got an early start? You might like to check in to one of these hotels near Chicago Midway International Airport the day before your Chicago to BOS flight:

  • 76% of all departures from Chicago Midway International Airport arrive within the expected time frame.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey time to RFD from the centre of Chicago is around 2 hours on public transport. If you prefer to travel by car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometres or so.

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

  • Flights that depart from RFD arrive at their final stop as scheduled 71% of the time.

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

About Boston Logan International Airport (BOS)

Getting from Boston Logan International Airport (BOS) to central Boston

  • From Boston Logan International Airport, central Boston is around 8 kilometres away. It takes about 20 minutes to get to the city centre by car.

  • Travelling by public transport typically takes 25 minutes.

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

  • The lowest price we've found for a one-way ticket from Chicago to Boston Logan International Airport is $97. For a return flight on this route, the best price is $218. Depending on when you want to go and the availability, these fares could change.

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

  • Plan your trip for June. That's the best month for landing cheap Chicago to Boston Logan International Airport tickets. If you're open to different travel dates, use the 'Whole month' tool to find the lowest price across every month.

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

  • Find a cheap flight from Chicago to Boston Logan International Airport by using the search filters. Choose your ideal departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

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

  • Think about the kind of holiday you want when picking your flight dates. December is the quietest month to visit Boston. July is when most people book flights from Chicago to Boston Logan International Airport (BOS), which may be perfect if you enjoy travelling when it's busier.

  • The warmest month in Boston is July, with temperatures ranging between 16ºC (61ºF) and 29ºC (84ºF). Book your Chicago to BOS plane ticket then if this is the type of weather you enjoy.

  • January has temperatures of between -8ºC (18ºF) and 6ºC (43ºF). Look for cheap tickets from Chicago to Boston Logan International Airport around that time if you want to travel in cooler conditions.

More about Boston

  • Start your Boston trip off on the right foot by choosing the perfect place to stay. After booking your flight from Chicago to Boston Logan International Airport, browse our range of hotels including:

  • Your Boston trip should come with a bit of sightseeing. Major attractions you won't want to miss include Museum of Fine Arts Boston, Freedom Trail and Boston Tea Party Ships & Museum.

Explore more of the United States

  • You've seen Boston, now it's time to discover other corners of the United States. Travel about 290 kilometres southwest to Yonkers to tick off its top attractions. From LEGOLAND Discovery Centre Westchester to Philipse Manor Hall and Old Croton Aqueduct Trailhead, there's plenty to keep you busy.

  • If you're ready to explore another great destination in the United States, head for Springfield, about 137 kilometres west of Boston. Titanic Museum, Basketball Hall of Fame and Springfield Museums are key highlights.

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