This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 24/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
18 Sep — 25 Sep1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 55 days in advance, depart on a Friday or Wednesday and return on a Friday
Cheap flight deals from Boston to Chicago
Enter your travel dates to find the best prices.
Cheapest
Best
Direct
Last-minute
One-way
Cheapest flights from Boston to Chicago
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 19 August 2026.
Sat 12/912:54 -
1 stop6h 29m
Wed 16/915:50 -
1 stop17h 32m
Deal found 17/8£146
Thu 1/1011:17 -
1 stop12h 42m
Thu 8/1017:54 -
1 stop16h 08m
Deal found 17/8£150
Sat 3/1012:54 -
1 stop6h 29m
Sat 10/1008:04 -
1 stop26h 40m
Deal found 19/8£168
Fri 11/911:36 -
1 stop12h 23m
Wed 16/915:50 -
1 stop17h 32m
Deal found 19/8£177
Thu 3/916:16 -
Nonstop3h 04m
Sun 6/907:55 -
Nonstop2h 29m
Deal found 18/8£188
Tue 22/906:19 -
1 stop8h 26m
Sat 26/920:24 -
Nonstop2h 45m
Deal found 16/8£189
Sat 12/906:19 -
1 stop8h 26m
Wed 16/909:38 -
Nonstop2h 28m
Deal found 18/8£190
Sat 19/914:45 -
1 stop9h 23m
Mon 21/920:24 -
Nonstop2h 45m
Deal found 15/8£191
Sun 13/906:19 -
1 stop8h 26m
Tue 22/915:00 -
1 stop7h 39m
Deal found 18/8£192
Mon 14/917:00 -
Nonstop3h 01m
Tue 15/910:59 -
1 stop5h 22m
Deal found 17/8£193
Best flights from Boston to Chicago
Discover carefully curated flight deals from Boston to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 19 August 2026.
Tue 13/1007:30 -
Nonstop2h 54m
Wed 14/1015:05 -
Nonstop2h 39m
Deal found 18/8£188
Sun 30/808:15 -
Nonstop2h 56m
Sat 5/913:49 -
Nonstop3h 10m
Deal found 16/8£188
Tue 17/1109:12 -
Nonstop3h 03m
Sat 21/1109:13 -
Nonstop2h 33m
Deal found 15/8£188
Tue 22/908:30 -
1 stop5h 30m
Wed 23/916:20 -
1 stop4h 50m
Deal found 17/8£203
Sat 12/907:30 -
Nonstop2h 54m
Wed 16/919:30 -
Nonstop2h 39m
Deal found 17/8£188
Fri 18/920:30 -
1 stop4h 58m
Sun 20/919:55 -
Nonstop2h 35m
Deal found 18/8£195
Thu 1/1014:45 -
1 stop9h 23m
Thu 8/1020:24 -
Nonstop2h 34m
Deal found 17/8£199
Fri 2/1007:30 -
Nonstop2h 54m
Sun 4/1007:35 -
Nonstop2h 33m
Deal found 16/8£188
Wed 21/1005:45 -
1 stop4h 53m
Sun 25/1021:20 -
Nonstop2h 26m
Deal found 17/8£195
Sun 20/907:00 -
Nonstop2h 48m
Fri 25/920:24 -
Nonstop2h 45m
Deal found 19/8£203
Thu 1/1016:30 -
Nonstop2h 58m
Thu 8/1007:25 -
Nonstop2h 35m
Deal found 17/8£188
Mon 7/907:30 -
Nonstop2h 56m
Tue 15/913:55 -
1 stop4h 51m
Deal found 16/8£210
Direct flights from Boston to Chicago
Explore direct flight options from Boston to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 19 August 2026.
Thu 3/916:16 -
Nonstop3h 04m
Wed 9/910:29 -
Nonstop2h 36m
Deal found 18/8£188
Thu 3/920:50 -
Nonstop2h 54m
Sun 6/907:55 -
Nonstop2h 29m
Deal found 18/8£189
Thu 5/1117:00 -
Nonstop3h 12m
Mon 9/1120:24 -
Nonstop2h 32m
Deal found 18/8£195
Mon 28/907:01 -
Nonstop2h 59m
Fri 2/1019:50 -
Nonstop2h 34m
Deal found 18/8£197
Wed 2/916:16 -
Nonstop3h 04m
Thu 3/907:55 -
Nonstop2h 29m
Deal found 18/8£200
Mon 7/907:30 -
Nonstop2h 56m
Thu 17/907:35 -
Nonstop2h 33m
Deal found 18/8£203
Thu 8/1006:00 -
Nonstop2h 59m
Fri 9/1021:24 -
Nonstop2h 30m
Deal found 16/8£205
Thu 31/1214:46 -
Nonstop3h 02m
Sat 9/107:40 -
Nonstop2h 25m
Deal found 15/8£206
Tue 8/920:50 -
Nonstop2h 42m
Wed 9/919:30 -
Nonstop2h 39m
Deal found 17/8£207
Wed 23/1205:45 -
Nonstop3h 06m
Sun 27/1221:49 -
Nonstop2h 29m
Deal found 16/8£208
Mon 14/917:00 -
Nonstop3h 01m
Tue 15/909:38 -
Nonstop2h 28m
Deal found 19/8£210
Sat 29/807:30 -
Nonstop2h 56m
Tue 8/910:29 -
Nonstop2h 36m
Deal found 17/8£211
Last-minute flights from Boston to Chicago
Discover last-minute flight deals from Boston to Chicago. Data last updated 19 August 2026 and is based on user searches.
Thu 3/916:16 -
Nonstop3h 04m
Wed 9/910:29 -
Nonstop2h 36m
Deal found 18/8£188
Thu 3/920:50 -
Nonstop2h 54m
Sun 6/907:55 -
Nonstop2h 29m
Deal found 18/8£189
Fri 11/911:36 -
1 stop12h 23m
Wed 16/915:50 -
1 stop17h 32m
Deal found 19/8£177
Sat 12/912:54 -
1 stop6h 29m
Wed 16/915:50 -
1 stop17h 32m
Deal found 17/8£146
Sat 12/906:19 -
1 stop8h 26m
Wed 16/909:38 -
Nonstop2h 28m
Deal found 18/8£190
Sun 13/906:19 -
1 stop8h 26m
Tue 22/915:00 -
1 stop7h 39m
Deal found 18/8£192
Mon 14/917:00 -
Nonstop3h 01m
Tue 15/910:59 -
1 stop5h 22m
Deal found 17/8£193
Sat 19/914:45 -
1 stop9h 23m
Mon 21/920:24 -
Nonstop2h 45m
Deal found 15/8£191
Tue 22/906:19 -
1 stop8h 26m
Sat 26/920:24 -
Nonstop2h 45m
Deal found 16/8£189
Mon 28/907:01 -
Nonstop2h 59m
Fri 2/1019:50 -
Nonstop2h 34m
Deal found 18/8£197
Wed 30/914:40 -
1 stop9h 28m
Mon 5/1010:59 -
1 stop5h 25m
Deal found 18/8£195
One-way flights from Boston to Chicago
Search for one-way flight options from Boston to Chicago. Find affordable one-way fares based on user searches. Data last updated 19 August 2026.
Mon 24/812:45 -
1 stop8h 14m
Deal found 15/8£88
Mon 14/912:54 -
1 stop6h 29m
Deal found 18/8£91
Wed 16/907:46 -
Nonstop2h 59m
Deal found 18/8£94
Sat 29/818:50 -
Nonstop3h 04m
Deal found 15/8£95
Wed 30/914:40 -
1 stop9h 28m
Deal found 18/8£96
Fri 1/117:00 -
1 stop6h 15m
Deal found 18/8£98
Thu 22/1006:55 -
1 stop5h 52m
Deal found 17/8£99
Wed 2/916:16 -
Nonstop3h 04m
Deal found 17/8£100
Sun 20/920:30 -
1 stop4h 58m
Deal found 17/8£102
Fri 6/1117:00 -
Nonstop3h 12m
Deal found 18/8£103
Mon 31/807:30 -
Nonstop2h 56m
Deal found 17/8£104
Wed 25/1106:00 -
Nonstop3h 00m
Deal found 17/8£105
Find flight deals from Boston to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 19 August 2026.
Customise your flight search to find flights from Boston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated 19 August 2026.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest return flight
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 13/10
07:30-09:24
Nonstop2h 54m
Chicago O'Hare Intl
Wed 14/10
15:05-18:44
Nonstop2h 39m
£188
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 30/8
08:15-10:11
Nonstop2h 56m
Chicago O'Hare Intl
Sat 5/9
13:49-17:59
Nonstop3h 10m
£188
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 17/11
09:12-11:15
Nonstop3h 03m
Chicago O'Hare Intl
Sat 21/11
09:13-12:46
Nonstop2h 33m
£188
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 12/9
07:30-09:24
Nonstop2h 54m
Chicago O'Hare Intl
Wed 16/9
19:30-23:09
Nonstop2h 39m
£188
Fastest return journey
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 2/10
07:30-09:24
Nonstop2h 54m
Chicago O'Hare Intl
Sun 4/10
07:35-11:08
Nonstop2h 33m
£188
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 1/10
16:30-18:28
Nonstop2h 58m
Chicago O'Hare Intl
Thu 8/10
07:25-11:00
Nonstop2h 35m
£188
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 18/9
20:30-00:28
1 stop4h 58m
Chicago O'Hare Intl
Sun 20/9
19:55-23:30
Nonstop2h 35m
£195
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 21/10
05:45-09:38
1 stop4h 53m
Chicago O'Hare Intl
Sun 25/10
21:20-00:46
Nonstop2h 26m
£195
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 1/10
14:45-23:08
1 stop9h 23m
Chicago O'Hare Intl
Thu 8/10
20:24-23:58
Nonstop2h 34m
£199
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 22/9
08:30-13:00
1 stop5h 30m
Chicago O'Hare Intl
Wed 23/9
16:20-22:10
1 stop4h 50m
£203
Flights are sorted by cheapest return flights first.
Deals found on 15/8
Showing 1-10 of 23 resultsSorted by cheapest first
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Best time to book a flight from Boston to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston with our price prediction graph.
BOS-CHI
BOS-ORD
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Boston to Chicago
BOS-CHI
BOS-ORD
What is the cheapest month to book a flight from Boston to Chicago?
Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £145). Flying from Boston to Chicago in June is currently the most expensive (average of £203). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from BOS to CHI?
Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 19 August 2026.
When flying from Boston to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 64% versus a flight in the afternoon.
Weekly flight availability from Boston to Chicago
Explore weekly flight availability from Boston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 19 August 2026.
The most flights from BOS to CHI are scheduled on a Monday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost for a return flight from Boston to Chicago?
Airfare is below average for this route at the moment.
Boston to Chicago flights typically cost between £150 and £241 in September.The cheapest return price found within the last 5 days was £146 on Frontier (12 Sept–16 Sept).
How often are flights from Boston to Chicago delayed?
About 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 171 minutes.
What is the most punctual flight time for Boston to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Boston to Chicago flights?
Over the past year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
How far ahead should I book a flight from Boston to Chicago?
The best time to book flights from Boston to Chicago is 14 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 19 August 2026.
Get a feel of what it's like to fly with American Airlines from Boston to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
Related info for your journey
Find useful and relevant information for your journey from Boston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
What airport do you fly from for flights from Boston to Chicago?
Boston Logan Intl (BOS) is the airport you will fly out of if you book a flight from Boston to Chicago. You should not have trouble finding flights to Chicago from Logan Intl; the airport handles an average of 59 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.
How long is the flight from Boston to Chicago?
A quick flight from Boston to Chicago can take about 2h 54m. Delta provides one of the quickest options available for as low as £188. Airlines will cover a distance of 864 mi. All flights are typically direct.
What are the most reliable airlines from Boston to Chicago?
No one likes to see their flight delayed. When booking a flight from Boston to Chicago consider choosing Japan Airlines (83%), Envoy Air (79%) or ANA (78%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Boston to Chicago?
The cheapest flight price from Boston to Chicago is £106. On average you can expect to pay £211. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £188.
Can I find deals for business class flights from Boston to Chicago?
Yes. Cheapflights offers flight deals from Boston to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Boston to Chicago?
Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £145). Flying from Boston to Chicago in June is currently the most expensive (average of £203). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 19 August 2026.
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Boston to Chicago?
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Boston today with Cheapflights!
Why should you use Cheapflights to find cheap flight tickets from Boston to Chicago?
Cheapflights helps you find that perfect flight to Chicago from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Boston to Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Boston to Chicago become cheaper?
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Boston today and book when prices fit your budget.
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