Cheap flights from Chicago O'Hare Intl Airport to Boston from £83
This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
24 Nov — 1 Dec1
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 February, booked 48 days in advance, depart on a Friday or Wednesday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Boston
Enter your travel dates to find the best prices.
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Best
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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 25 October 2026.
Tue 17/1107:00 -
Nonstop2h 19m
Tue 17/1115:41 -
1 stop7h 37m
Deal found 21/10£164
Fri 18/1218:24 -
Nonstop2h 35m
Mon 11/115:32 -
1 stop5h 36m
Deal found 23/10£165
Mon 23/1117:05 -
1 stop5h 49m
Mon 4/113:50 -
Nonstop3h 00m
Deal found 23/10£166
Thu 12/1107:00 -
1 stop4h 25m
Sun 15/1116:35 -
Nonstop3h 09m
Deal found 21/10£167
Sat 14/1105:00 -
1 stop4h 51m
Sat 14/1115:41 -
1 stop7h 44m
Deal found 22/10£170
Fri 20/1113:59 -
Nonstop2h 25m
Mon 23/1109:00 -
1 stop5h 09m
Deal found 22/10£173
Sat 21/1118:15 -
1 stop5h 53m
Tue 1/1215:00 -
1 stop6h 45m
Deal found 21/10£174
Fri 20/1115:44 -
Nonstop2h 30m
Fri 27/1106:00 -
Nonstop3h 00m
Deal found 21/10£177
Mon 7/1207:00 -
1 stop5h 24m
Mon 7/1219:33 -
1 stop4h 56m
Deal found 22/10£179
Fri 20/1107:05 -
Nonstop2h 27m
Sat 9/117:15 -
Nonstop2h 54m
Deal found 23/10£181
Fri 20/1107:05 -
Nonstop2h 27m
Sat 5/1213:35 -
Nonstop3h 02m
Deal found 21/10£182
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 25 October 2026.
Tue 24/1106:00 -
1 stop5h 25m
Mon 4/113:50 -
Nonstop3h 00m
Deal found 23/10£166
Thu 11/209:10 -
Nonstop2h 26m
Thu 25/209:50 -
1 stop4h 57m
Deal found 20/10£167
Fri 13/1115:05 -
Nonstop2h 24m
Mon 16/1116:00 -
1 stop7h 18m
Deal found 22/10£167
Sun 24/107:10 -
Nonstop2h 28m
Fri 29/107:15 -
1 stop5h 35m
Deal found 20/10£167
Sat 5/1213:34 -
1 stop6h 32m
Sat 12/1207:40 -
Nonstop3h 11m
Deal found 21/10£167
Wed 10/218:50 -
Nonstop2h 35m
Wed 24/206:00 -
1 stop7h 36m
Deal found 20/10£167
Thu 12/1107:00 -
1 stop4h 25m
Sat 14/1112:20 -
1 stop5h 45m
Deal found 20/10£174
Mon 21/1213:26 -
1 stop6h 26m
Tue 22/1216:52 -
1 stop4h 26m
Deal found 21/10£174
Sun 6/1206:00 -
1 stop6h 21m
Sun 13/1207:30 -
Nonstop3h 08m
Deal found 22/10£198
Thu 12/1108:29 -
1 stop6h 23m
Sun 15/1105:30 -
1 stop6h 09m
Deal found 21/10£205
Sun 20/1217:45 -
Nonstop2h 29m
Sat 26/1205:30 -
1 stop5h 19m
Deal found 22/10£220
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 25 October 2026.
Fri 20/1115:44 -
Nonstop2h 30m
Fri 27/1106:00 -
Nonstop3h 00m
Deal found 21/10£177
Fri 20/1107:05 -
Nonstop2h 27m
Sat 9/117:15 -
Nonstop2h 54m
Deal found 23/10£181
Fri 20/1107:05 -
Nonstop2h 27m
Sat 5/1213:35 -
Nonstop3h 02m
Deal found 21/10£182
Thu 12/1107:05 -
Nonstop2h 27m
Thu 12/1120:40 -
Nonstop2h 56m
Deal found 23/10£190
Mon 21/1219:55 -
Nonstop2h 26m
Thu 24/1216:45 -
Nonstop3h 13m
Deal found 22/10£191
Sat 21/1116:40 -
Nonstop2h 23m
Tue 1/1207:30 -
Nonstop3h 08m
Deal found 21/10£193
Thu 19/1110:35 -
Nonstop2h 24m
Sun 22/1120:40 -
Nonstop2h 56m
Deal found 25/10£194
Mon 9/1119:45 -
Nonstop2h 23m
Tue 10/1120:40 -
Nonstop2h 56m
Deal found 21/10£197
Thu 24/1219:55 -
Nonstop2h 26m
Sun 3/116:45 -
Nonstop3h 13m
Deal found 22/10£197
Sat 26/1219:55 -
Nonstop2h 26m
Wed 30/1216:45 -
Nonstop3h 13m
Deal found 20/10£199
Sat 21/1107:00 -
Nonstop2h 19m
Wed 25/1120:25 -
Nonstop3h 04m
Deal found 21/10£202
Thu 5/1113:00 -
Nonstop2h 48m
Mon 9/1117:05 -
Nonstop3h 12m
Deal found 21/10£205
Last-minute flights from O'Hare Intl to Boston
Discover last-minute flight deals from O'Hare Intl to Boston. Data last updated 25 October 2026 and is based on user searches.
Thu 12/1107:00 -
1 stop4h 25m
Sun 15/1116:35 -
Nonstop3h 09m
Deal found 21/10£167
Sat 14/1105:00 -
1 stop4h 51m
Sat 14/1115:41 -
1 stop7h 44m
Deal found 22/10£170
Mon 16/1106:05 -
Nonstop2h 18m
Mon 23/1105:30 -
1 stop5h 15m
Deal found 23/10£165
Tue 17/1107:00 -
Nonstop2h 19m
Tue 17/1115:41 -
1 stop7h 37m
Deal found 21/10£164
Thu 19/1111:56 -
1 stop4h 31m
Fri 27/1106:00 -
Nonstop3h 00m
Deal found 21/10£185
Fri 20/1113:59 -
Nonstop2h 25m
Mon 23/1109:00 -
1 stop5h 09m
Deal found 22/10£173
Fri 20/1115:44 -
Nonstop2h 30m
Fri 27/1106:00 -
Nonstop3h 00m
Deal found 21/10£177
Fri 20/1107:05 -
Nonstop2h 27m
Sat 9/117:15 -
Nonstop2h 54m
Deal found 23/10£181
Fri 20/1107:05 -
Nonstop2h 27m
Mon 23/1120:40 -
Nonstop2h 56m
Deal found 20/10£182
Sat 21/1118:15 -
1 stop5h 53m
Tue 1/1215:00 -
1 stop6h 45m
Deal found 21/10£174
Mon 23/1119:45 -
Nonstop2h 23m
Thu 7/112:00 -
1 stop5h 12m
Deal found 23/10£166
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 25 October 2026.
Wed 11/1105:00 -
1 stop4h 51m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 23/10£83
Mon 9/1105:00 -
1 stop4h 51m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 23/10£87
Mon 9/1117:42 -
1 stop5h 02m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 21/10£87
Fri 1/111:09 -
1 stop4h 44m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 20/10£94
Sun 15/1105:00 -
1 stop5h 07m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 23/10£95
Mon 22/209:15 -
Nonstop2h 26m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 23/10£97
Tue 1/1218:15 -
1 stop4h 44m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 20/10£98
Sun 22/1107:05 -
Nonstop2h 27m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 23/10£99
Wed 30/1205:00 -
1 stop6h 10m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 22/10£99
Fri 20/1107:05 -
Nonstop2h 27m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 21/10£102
Sat 21/1105:00 -
1 stop4h 51m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 22/10£108
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 25 October 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 25 October 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
Wed 18/11
07:00-12:25
1 stop4h 25m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£87
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 16/12
05:55-12:27
1 stop5h 32m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£87
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 22/2
17:45-23:34
1 stop4h 49m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£87
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 6/12
07:00-12:27
1 stop4h 27m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£87
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 19/12
10:30-16:04
1 stop4h 34m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£87
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 9/11
17:42-23:44
1 stop5h 02m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£87
Fastest return journey
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 22/2
09:10-12:36
Nonstop2h 26m
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
Mon 9/11
05:00-10:51
1 stop4h 51m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£120
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/11
07:00-13:31
1 stop5h 31m
Boston Logan Intl
Wed 31/12
00:00-23:00
Nonstop0h 00m
£120
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
£123
Flights are sorted by cheapest return flights first.
Deals found on 21/10
Showing 1-10 of 22 resultsSorted by cheapest first
1
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 47 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 £154). Flying from Chicago O'Hare Intl Airport to Boston in October is currently the most expensive (average of £253). 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 25 October 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 below average for this route at the moment.
Chicago O'Hare Intl Airport to Boston flights typically cost between £168 and £307 in November.The cheapest return price found within the last 5 days was £164 on United Airlines (17 Nov–17 Nov).
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 25 October 2026.
The most flights from ORD to BOS are scheduled on a Friday (70 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 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 159 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 Sunday 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 22% 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 26 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 £167, Delta can have you in Boston from Chicago O'Hare Intl Airport in 2h 29m. 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 (88%), Avianca (85%), ITA Airways (81%).
What are the cheapest flights from Chicago O'Hare Intl Airport to Boston?
Looking at all options, your cheapest flight can be booked for £223. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for £159 on average, our data indicates £301 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 £154). Flying from Chicago O'Hare Intl Airport to Boston in October is currently the most expensive (average of £253). 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
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North Truro
Warwick
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Wellfleet
Peabody
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Raynham
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Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 25 October 2026.
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on 25 October 2026.
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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.
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