Cheap flights from Chicago O'Hare Intl Airport to Boston from £44
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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in September or January, booked 72 days in advance, depart on a Saturday or Thursday and return on a Wednesday
Cheap 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 28 October 2025.
Find flight deals from O'Hare Intl to Boston
Cheapest flights from O'Hare Intl to BostonExplore 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 28 October 2025.
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 28 October 2025.
Cheapflights Fare Finder
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
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 25/12
21:12-00:45
Nonstop2h 33m
Boston Logan Intl
Thu 1/1
06:01-08:05
Nonstop3h 04m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 27/11
07:45-11:09
Nonstop2h 24m
Boston Logan Intl
Sat 6/12
12:50-14:47
Nonstop2h 57m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 27/11
06:15-09:30
Nonstop2h 15m
Boston Logan Intl
Wed 3/12
12:50-14:50
Nonstop3h 00m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/12
07:10-10:36
Nonstop2h 26m
Boston Logan Intl
Mon 8/12
16:05-18:02
Nonstop2h 57m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/12
07:10-10:36
Nonstop2h 26m
Boston Logan Intl
Sun 7/12
07:30-09:33
Nonstop3h 03m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 13/11
11:20-14:44
Nonstop2h 24m
Boston Logan Intl
Sun 16/11
08:30-10:35
Nonstop3h 05m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 14/11
18:55-22:27
Nonstop2h 32m
Boston Logan Intl
Mon 17/11
08:30-10:35
Nonstop3h 05m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 13/11
06:15-09:30
Nonstop2h 15m
Boston Logan Intl
Tue 18/11
16:15-18:10
Nonstop2h 55m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 11/12
09:19-12:43
Nonstop2h 24m
Boston Logan Intl
Sun 11/1
18:21-20:25
Nonstop3h 04m
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 10/11
21:25-00:45
Nonstop2h 20m
Boston Logan Intl
Thu 13/11
16:15-18:10
Nonstop2h 55m
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.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Boston
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Boston?
Booking 72 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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £53). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of £103). 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?
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 78% on your trip compared to booking a flight at midday.
How often are flights from Chicago to Boston delayed?
About 20% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 151 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 Thursday 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, Etihad Airways have had the lowest number of delays on this route, with just 9% 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.
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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.