Cheap flights from Chicago O'Hare Intl Airport to Boston from £87
This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 23/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
10 Oct — 17 Oct1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in January or November, booked 61 days in advance, depart on a Friday or Wednesday and return on a Thursday
Cheap flight deals from O'Hare Intl to Boston
Enter your travel dates to find the best prices.
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Best
Direct
Last-minute
One-way
Cheapest flights from O'Hare Intl to Boston
Explore the most affordable flight options available from O'Hare Intl to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 September 2026.
Fri 23/1020:11 -
1 stop13h 51m
Tue 27/1011:12 -
1 stop8h 33m
Deal found 8/9£175
Sat 24/1007:25 -
Nonstop2h 35m
Sat 31/1018:45 -
Nonstop3h 01m
Deal found 9/9£184
Thu 1/1020:24 -
Nonstop2h 45m
Sun 4/1007:00 -
Nonstop2h 48m
Deal found 10/9£184
Sun 20/909:38 -
Nonstop2h 28m
Thu 24/907:00 -
Nonstop2h 48m
Deal found 8/9£188
Wed 7/1010:24 -
Nonstop2h 30m
Tue 13/1019:40 -
Nonstop2h 51m
Deal found 9/9£193
Wed 7/1010:59 -
1 stop5h 25m
Tue 13/1006:55 -
1 stop5h 29m
Deal found 9/9£196
Fri 16/1012:38 -
1 stop7h 57m
Mon 19/1015:41 -
1 stop7h 29m
Deal found 10/9£197
Sat 3/1010:59 -
1 stop6h 01m
Mon 5/1016:10 -
1 stop6h 50m
Deal found 9/9£198
Thu 15/1009:38 -
Nonstop2h 28m
Fri 16/1017:12 -
Nonstop3h 02m
Deal found 9/9£202
Best flights from O'Hare Intl to Boston
Discover carefully curated flight deals from O'Hare Intl to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 10 September 2026.
Sat 24/1007:25 -
Nonstop2h 35m
Sat 31/1018:45 -
Nonstop3h 01m
Deal found 9/9£184
Thu 29/1006:59 -
1 stop4h 27m
Sun 1/1107:31 -
Nonstop3h 03m
Deal found 9/9£191
Wed 7/1010:59 -
1 stop5h 25m
Tue 13/1006:55 -
1 stop5h 29m
Deal found 9/9£196
Wed 21/1007:00 -
1 stop5h 29m
Sat 24/1009:05 -
1 stop6h 55m
Deal found 9/9£199
Fri 25/921:24 -
Nonstop2h 30m
Mon 28/920:30 -
Nonstop2h 59m
Deal found 9/9£203
Fri 30/1015:05 -
Nonstop2h 39m
Sat 31/1012:20 -
1 stop6h 27m
Deal found 9/9£201
Thu 15/1010:24 -
Nonstop2h 30m
Thu 15/1019:40 -
Nonstop2h 51m
Deal found 5/9£218
Fri 30/1007:25 -
Nonstop2h 35m
Sun 1/1105:50 -
1 stop6h 50m
Deal found 8/9£232
Tue 29/907:00 -
1 stop5h 22m
Wed 30/918:00 -
1 stop5h 18m
Deal found 6/9£234
Sat 17/1006:10 -
1 stop7h 39m
Tue 20/1006:50 -
1 stop6h 23m
Deal found 8/9£234
Direct flights from O'Hare Intl to Boston
Explore direct flight options from O'Hare Intl to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated 10 September 2026.
Sat 24/1007:25 -
Nonstop2h 35m
Sat 31/1018:45 -
Nonstop3h 01m
Deal found 9/9£184
Thu 1/1020:24 -
Nonstop2h 45m
Sun 4/1007:00 -
Nonstop2h 48m
Deal found 10/9£184
Sun 20/909:38 -
Nonstop2h 28m
Thu 24/907:00 -
Nonstop2h 48m
Deal found 8/9£188
Wed 7/1010:24 -
Nonstop2h 30m
Tue 13/1019:40 -
Nonstop2h 51m
Deal found 9/9£193
Thu 15/1009:38 -
Nonstop2h 28m
Fri 16/1017:12 -
Nonstop3h 02m
Deal found 9/9£202
Sat 24/1007:25 -
Nonstop2h 35m
Tue 27/1016:25 -
Nonstop2h 55m
Deal found 7/9£203
Fri 9/1020:00 -
Nonstop2h 58m
Sun 11/1006:55 -
Nonstop2h 52m
Deal found 9/9£209
Sun 18/1007:25 -
Nonstop2h 35m
Sat 24/1007:50 -
Nonstop2h 58m
Deal found 7/9£210
Wed 7/1009:39 -
Nonstop2h 28m
Mon 12/1006:55 -
Nonstop2h 52m
Deal found 9/9£212
Fri 9/1020:00 -
Nonstop2h 58m
Tue 13/1006:55 -
Nonstop2h 52m
Deal found 9/9£217
Fri 16/1019:10 -
Nonstop2h 43m
Wed 21/1016:25 -
Nonstop2h 55m
Deal found 7/9£218
Last-minute flights from O'Hare Intl to Boston
Discover last-minute flight deals from O'Hare Intl to Boston. Data last updated 10 September 2026 and is based on user searches.
Sun 20/909:38 -
Nonstop2h 28m
Thu 24/907:00 -
Nonstop2h 48m
Deal found 8/9£188
Thu 1/1020:24 -
Nonstop2h 45m
Sun 4/1007:00 -
Nonstop2h 48m
Deal found 10/9£184
Sat 3/1010:59 -
1 stop6h 01m
Mon 5/1016:10 -
1 stop6h 50m
Deal found 9/9£198
Wed 7/1010:24 -
Nonstop2h 30m
Tue 13/1019:40 -
Nonstop2h 51m
Deal found 9/9£193
Wed 7/1010:59 -
1 stop5h 25m
Tue 13/1006:55 -
1 stop5h 29m
Deal found 9/9£196
Thu 15/1009:38 -
Nonstop2h 28m
Fri 16/1017:12 -
Nonstop3h 02m
Deal found 9/9£202
Fri 16/1012:38 -
1 stop7h 57m
Mon 19/1015:41 -
1 stop7h 29m
Deal found 10/9£197
Fri 23/1020:11 -
1 stop13h 51m
Tue 27/1011:12 -
1 stop8h 33m
Deal found 8/9£175
Sat 24/1007:25 -
Nonstop2h 35m
Sat 31/1018:45 -
Nonstop3h 01m
Deal found 9/9£184
One-way flights from O'Hare Intl to Boston
Search for one-way flight options from O'Hare Intl to Boston. Find affordable one-way fares based on user searches. Data last updated 10 September 2026.
Wed 23/915:50 -
1 stop17h 32m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 8/9£87
Thu 22/1012:38 -
1 stop7h 11m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 5/9£88
Sat 26/920:24 -
Nonstop2h 45m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 10/9£92
Sat 7/1118:08 -
1 stop6h 12m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 9/9£100
Wed 23/915:35 -
Nonstop2h 44m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 9/9£102
Tue 22/910:59 -
1 stop5h 22m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 10/9£103
Wed 2/1215:05 -
Nonstop2h 31m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 10/9£106
Wed 23/907:35 -
Nonstop2h 33m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 7/9£109
Thu 1/1007:35 -
Nonstop2h 33m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 6/9£112
Tue 6/1019:10 -
Nonstop2h 43m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 6/9£116
Find flight deals from O'Hare Intl to Boston
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 10 September 2026.
Customise your flight search to find flights from O'Hare Intl 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 10 September 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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
Sat 24/10
08:50-14:55
1 stop5h 05m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£100
Fastest return journey
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 5/11
12:00-15:32
Nonstop2h 32m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£102
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 21/11
17:42-23:44
1 stop5h 02m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£124
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 24/9
07:30-14:35
1 stop6h 05m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£138
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 28/10
11:56-18:34
1 stop5h 38m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£146
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 22/10
07:25-11:00
Nonstop2h 35m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£173
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 24/10
07:25-11:00
Nonstop2h 35m
Boston Logan Intl
Sat 31/10
18:45-20:46
Nonstop3h 01m
£184
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 30/9
10:29-14:05
Nonstop2h 36m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£190
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 29/10
06:59-12:26
1 stop4h 27m
Boston Logan Intl
Sun 1/11
07:31-09:34
Nonstop3h 03m
£191
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 7/10
10:59-17:24
1 stop5h 25m
Boston Logan Intl
Tue 13/10
06:55-11:24
1 stop5h 29m
£196
Flights are sorted by cheapest return flights first.
Deals found on 9/9
Showing 1-10 of 21 resultsSorted by cheapest first
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2
3
Best time to book a flight from O'Hare Intl to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from O'Hare Intl with our price prediction graph.
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 O'Hare Intl Airport to Boston
Prices
Airlines
Delays
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Boston?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £152). Flying from Chicago O'Hare Intl Airport to Boston in August is currently the most expensive (average of £228). 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 ORD to BOS?
Find hourly flight availability from O'Hare Intl 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 10 September 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 80% on your trip compared to booking a flight at midday.
How much does it cost for a return flight from Chicago O'Hare Intl Airport to Boston?
Airfare is typical for this route at the moment.
Chicago O'Hare Intl Airport to Boston flights typically cost between £154 and £255 in October.The cheapest return price found within the last 5 days was £175 on Frontier (23 Oct–27 Oct).
Weekly flight availability from Chicago O'Hare Intl Airport to Boston
Explore weekly flight availability from O'Hare Intl 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 10 September 2026.
The most flights from ORD to BOS are scheduled on a Wednesday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 on average).
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 156 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 20% of flights being delayed.
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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 O'Hare Intl?
Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago O'Hare Intl. On average, Logan Intl has 46 inbound flights from Chicago O'Hare Intl 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 O'Hare Intl Airport to Boston?
For as low as £184, Delta can have you in Boston from Chicago O'Hare Intl Airport in 2h 35m. There are 864 mi between Chicago O'Hare Intl Airport and Boston. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.
What are the most reliable airlines from Chicago O'Hare Intl Airport to Boston?
Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago O'Hare Intl Airport to Boston on time: Envoy Air (90%), Avianca (70%), KLM (69%).
What are the cheapest flights from Chicago O'Hare Intl Airport to Boston?
Looking at all options, your cheapest flight can be booked for £134. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for £196 on average, our data indicates £160 when flying from Chicago O'Hare Intl Airport to Boston.
Can I find deals for business class flights from O'Hare Intl to Boston?
Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £152). Flying from Chicago O'Hare Intl Airport to Boston in August is currently the most expensive (average of £228). 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.
Book flights to Boston if you plan to visit one of these locations
Burlington
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North Truro
Waltham
Warwick
Cambridge
Wellfleet
Peabody
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Quincy
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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 10 September 2026.
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on 10 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 O'Hare Intl to Boston?
Cheapflights makes it easy to find O'Hare Intl to Boston flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from O'Hare Intl to Boston?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Boston from O'Hare Intl.
Can Cheapflights find flights from O'Hare Intl to Boston with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from O'Hare Intl to Boston, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from O'Hare Intl to Boston become cheaper?
Yes, Cheapflights offers price alerts on O'Hare Intl to Boston flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.
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