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 28/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
2 Oct — 9 Oct1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in January or February, booked 54 days in advance, depart on a Friday or Wednesday and return on a Friday
Cheap flight deals from Chicago to Boston
Enter your travel dates to find the best prices.
Cheapest
Best
Direct
Last-minute
One-way
Cheapest flights from Chicago to Boston
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 2 September 2026.
Thu 1/1010:30 -
Nonstop2h 35m
Mon 5/1020:50 -
Nonstop2h 42m
Deal found 1/9£160
Thu 1/1020:24 -
Nonstop2h 45m
Mon 5/1017:00 -
Nonstop3h 03m
Deal found 1/9£161
Wed 23/910:29 -
Nonstop2h 36m
Fri 25/920:50 -
Nonstop2h 42m
Deal found 1/9£167
Fri 16/1019:10 -
Nonstop2h 43m
Fri 23/1019:40 -
Nonstop2h 51m
Deal found 1/9£174
Sat 7/1108:06 -
Nonstop2h 30m
Fri 13/1109:23 -
1 stop4h 36m
Deal found 1/9£174
Thu 17/907:35 -
Nonstop2h 33m
Sun 20/907:30 -
Nonstop2h 54m
Deal found 28/8£182
Fri 2/1015:05 -
Nonstop2h 47m
Mon 5/1020:50 -
Nonstop2h 42m
Deal found 1/9£184
Thu 22/1018:58 -
1 stop15h 04m
Mon 26/1012:57 -
1 stop6h 34m
Deal found 28/8£185
Wed 30/910:59 -
1 stop5h 22m
Sun 4/1007:00 -
Nonstop2h 48m
Deal found 1/9£187
Mon 14/920:24 -
Nonstop2h 45m
Thu 17/917:00 -
Nonstop3h 01m
Deal found 29/8£188
Fri 18/910:30 -
Nonstop2h 35m
Mon 21/916:30 -
Nonstop2h 58m
Deal found 1/9£189
Best flights from Chicago to Boston
Discover carefully curated flight deals from Chicago to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 2 September 2026.
Fri 25/921:24 -
Nonstop2h 30m
Sun 27/906:00 -
Nonstop2h 59m
Deal found 29/8£203
Mon 21/1207:05 -
Nonstop2h 28m
Mon 28/1216:52 -
1 stop4h 54m
Deal found 28/8£218
Sat 17/1009:38 -
Nonstop2h 28m
Sun 25/1017:15 -
Nonstop3h 14m
Deal found 29/8£218
Wed 11/1107:00 -
1 stop4h 26m
Mon 16/1117:00 -
Nonstop3h 01m
Deal found 28/8£211
Sat 12/915:40 -
1 stop5h 53m
Fri 18/907:30 -
Nonstop2h 54m
Deal found 30/8£225
Thu 15/1007:25 -
Nonstop2h 35m
Mon 19/1019:40 -
Nonstop2h 51m
Deal found 1/9£227
Thu 19/1109:13 -
Nonstop2h 33m
Mon 30/1109:12 -
Nonstop3h 03m
Deal found 29/8£248
Sat 14/1115:55 -
1 stop6h 27m
Sun 15/1105:30 -
1 stop5h 55m
Deal found 31/8£233
Sat 19/1221:49 -
Nonstop2h 29m
Tue 22/1205:45 -
Nonstop3h 06m
Deal found 1/9£258
Tue 22/913:51 -
1 stop6h 21m
Thu 24/905:40 -
1 stop5h 57m
Deal found 1/9£242
Sat 7/1118:08 -
1 stop6h 12m
Fri 13/1118:00 -
1 stop5h 18m
Deal found 1/9£248
Tue 3/1106:20 -
1 stop6h 50m
Thu 5/1109:15 -
1 stop4h 44m
Deal found 1/9£258
Direct flights from Chicago to Boston
Explore direct flight options from Chicago to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated 2 September 2026.
Thu 1/1010:30 -
Nonstop2h 35m
Mon 5/1020:50 -
Nonstop2h 42m
Deal found 1/9£160
Thu 1/1020:24 -
Nonstop2h 45m
Mon 5/1017:00 -
Nonstop3h 03m
Deal found 1/9£161
Wed 23/910:29 -
Nonstop2h 36m
Fri 25/920:50 -
Nonstop2h 42m
Deal found 1/9£167
Fri 16/1019:10 -
Nonstop2h 43m
Fri 23/1019:40 -
Nonstop2h 51m
Deal found 1/9£174
Thu 17/907:35 -
Nonstop2h 33m
Sun 20/907:30 -
Nonstop2h 54m
Deal found 28/8£182
Fri 2/1015:05 -
Nonstop2h 47m
Mon 5/1020:50 -
Nonstop2h 42m
Deal found 1/9£184
Mon 14/920:24 -
Nonstop2h 45m
Thu 17/917:00 -
Nonstop3h 01m
Deal found 29/8£188
Fri 18/910:30 -
Nonstop2h 35m
Mon 21/916:30 -
Nonstop2h 58m
Deal found 1/9£189
Mon 5/1007:35 -
Nonstop2h 33m
Mon 12/1019:40 -
Nonstop2h 51m
Deal found 28/8£194
Fri 30/1010:24 -
Nonstop2h 30m
Sun 1/1107:30 -
Nonstop2h 54m
Deal found 31/8£196
Wed 14/1009:38 -
Nonstop2h 28m
Sun 18/1006:55 -
Nonstop2h 52m
Deal found 1/9£197
Last-minute flights from Chicago to Boston
Discover last-minute flight deals from Chicago to Boston. Data last updated 2 September 2026 and is based on user searches.
Mon 14/920:24 -
Nonstop2h 45m
Thu 17/917:00 -
Nonstop3h 01m
Deal found 29/8£188
Thu 17/907:35 -
Nonstop2h 33m
Sun 20/907:30 -
Nonstop2h 54m
Deal found 28/8£182
Fri 18/910:30 -
Nonstop2h 35m
Mon 21/916:30 -
Nonstop2h 58m
Deal found 1/9£189
Wed 23/910:29 -
Nonstop2h 36m
Fri 25/920:50 -
Nonstop2h 42m
Deal found 1/9£167
Wed 30/910:59 -
1 stop5h 22m
Sun 4/1007:00 -
Nonstop2h 48m
Deal found 1/9£187
Thu 1/1010:30 -
Nonstop2h 35m
Mon 5/1020:50 -
Nonstop2h 42m
Deal found 1/9£160
Thu 1/1020:24 -
Nonstop2h 45m
Mon 5/1017:00 -
Nonstop3h 03m
Deal found 1/9£161
Fri 2/1015:05 -
Nonstop2h 47m
Mon 5/1020:50 -
Nonstop2h 42m
Deal found 1/9£184
Mon 5/1007:35 -
Nonstop2h 33m
Mon 12/1019:40 -
Nonstop2h 51m
Deal found 28/8£194
Fri 16/1019:10 -
Nonstop2h 43m
Fri 23/1019:40 -
Nonstop2h 51m
Deal found 1/9£174
Thu 22/1018:58 -
1 stop15h 04m
Mon 26/1012:57 -
1 stop6h 34m
Deal found 28/8£185
One-way flights from Chicago to Boston
Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated 2 September 2026.
Mon 28/919:30 -
Nonstop2h 39m
Deal found 28/8£81
Fri 2/1019:30 -
Nonstop2h 39m
Deal found 1/9£87
Mon 5/1015:05 -
Nonstop2h 47m
Deal found 31/8£92
Fri 6/1107:25 -
Nonstop2h 35m
Deal found 1/9£95
Thu 24/911:15 -
1 stop22h 36m
Deal found 31/8£101
Mon 21/907:30 -
Nonstop2h 31m
Deal found 28/8£102
Sun 20/907:35 -
Nonstop2h 33m
Deal found 28/8£106
Wed 18/1115:40 -
1 stop5h 06m
Deal found 28/8£109
Mon 14/918:15 -
1 stop4h 44m
Deal found 28/8£109
Wed 30/918:45 -
Nonstop2h 42m
Deal found 1/9£110
Thu 24/921:24 -
Nonstop2h 30m
Deal found 28/8£112
Tue 15/919:30 -
Nonstop2h 39m
Deal found 1/9£116
Find flight deals from Chicago to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Boston (BOS). 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 2 September 2026.
Customise your flight search to find flights from Chicago to Boston 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 2 September 2026.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest return flight
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 25/9
21:24-00:54
Nonstop2h 30m
Boston Logan Intl
Sun 27/9
06:00-07:59
Nonstop2h 59m
£203
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 11/11
07:00-12:26
1 stop4h 26m
Boston Logan Intl
Mon 16/11
17:00-19:01
Nonstop3h 01m
£211
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 21/12
07:05-10:33
Nonstop2h 28m
Boston Logan Intl
Mon 28/12
16:52-20:46
1 stop4h 54m
£218
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 17/10
09:38-13:06
Nonstop2h 28m
Boston Logan Intl
Sun 25/10
17:15-19:29
Nonstop3h 14m
£218
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 12/9
15:40-22:33
1 stop5h 53m
Boston Logan Intl
Fri 18/9
07:30-09:24
Nonstop2h 54m
£225
Fastest return journey
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 15/10
07:25-11:00
Nonstop2h 35m
Boston Logan Intl
Mon 19/10
19:40-21:31
Nonstop2h 51m
£227
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 14/11
15:55-23:22
1 stop6h 27m
Boston Logan Intl
Sun 15/11
05:30-10:25
1 stop5h 55m
£233
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 22/9
13:51-21:12
1 stop6h 21m
Boston Logan Intl
Thu 24/9
05:40-10:37
1 stop5h 57m
£242
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 19/11
09:13-12:46
Nonstop2h 33m
Boston Logan Intl
Mon 30/11
09:12-11:15
Nonstop3h 03m
£248
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 7/11
18:08-01:20
1 stop6h 12m
Boston Logan Intl
Fri 13/11
18:00-22:18
1 stop5h 18m
£248
Flights are sorted by cheapest return flights first.
Deals found on 1/9
Showing 1-10 of 23 resultsSorted by cheapest first
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2
3
Best time to book a flight from Chicago to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.
CHI-BOS
ORD-BOS
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 Chicago to Boston
CHI-BOS
ORD-BOS
What is the cheapest month to book a flight from Chicago to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of £148). Flying from Chicago to Boston in August is currently the most expensive (average of £214). 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 CHI to BOS?
Find hourly flight availability from Chicago to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 2 September 2026.
When flying from Chicago to Boston, 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 80% versus a flight at midday.
Weekly flight availability from Chicago to Boston
Explore weekly flight availability from Chicago to Boston. 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 2 September 2026.
The most flights from CHI to BOS are scheduled on a Monday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost for a return flight from Chicago to Boston?
Airfare is typical for this route at the moment.
Chicago to Boston flights typically cost between £151 and £238 in October.The cheapest return price found within the last 5 days was £160 on Delta (1 Oct–5 Oct).
How often are flights from Chicago to Boston delayed?
About 26% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 152 minutes.
What is the most punctual flight time for Chicago to Boston flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Boston flights?
Over the past year, Delta have had the lowest number of delays on this route, with just 21% of flights being delayed.
How far ahead should I book a flight from Chicago to Boston?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Boston. 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 into for flights to Boston from Chicago?
Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 43 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.
How long is the flight from Chicago to Boston?
Departing from Chicago to Boston will take you 2h 28m. Chicago and Boston are separated by a distance of 864 mi. Generally, flights for this route are direct.
What are the most reliable airlines from Chicago to Boston?
No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Envoy Air (92%), Air New Zealand (68%) or Royal Jordanian (68%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Chicago to Boston?
The cheapest flight price from Chicago to Boston is £134. On average you can expect to pay £161. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £167.
Can I find deals for business class flights from Chicago to Boston?
Yes. Cheapflights offers flight deals from Chicago to Boston 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 Chicago to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of £148). Flying from Chicago to Boston in August is currently the most expensive (average of £214). 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 Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 2 September 2026.
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on 2 September 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 Chicago to Boston?
Deals for Chicago to Boston flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Boston.
Can Cheapflights find flights from Chicago to Boston with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Boston, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?
Yes! Start tracking prices for Chicago to Boston flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.
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