Cheap flights from Boston to Chicago O'Hare Intl Airport 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 24/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
17 Oct — 24 Oct1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in January or February, booked 78 days in advance, depart on a Tuesday or Thursday and return on a Friday
Cheap flight deals from Boston to O'Hare Intl
Enter your travel dates to find the best prices.
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Best
Direct
Last-minute
One-way
Cheapest flights from Boston to O'Hare Intl
Explore the most affordable flight options available from Boston to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 September 2026.
Thu 1/1007:00 -
Nonstop2h 48m
Mon 5/1007:00 -
1 stop6h 29m
Deal found 17/9£162
Tue 3/1119:10 -
Nonstop2h 56m
Wed 4/1107:25 -
Nonstop2h 35m
Deal found 16/9£164
Mon 5/1016:10 -
1 stop6h 50m
Tue 6/1007:05 -
1 stop6h 24m
Deal found 14/9£165
Mon 5/1009:10 -
1 stop4h 49m
Wed 7/1010:05 -
1 stop7h 23m
Deal found 16/9£166
Sat 10/1019:40 -
Nonstop2h 51m
Sat 24/1007:25 -
Nonstop2h 35m
Deal found 15/9£167
Thu 15/1016:11 -
1 stop6h 59m
Mon 19/1006:10 -
1 stop7h 19m
Deal found 17/9£168
Thu 8/1006:00 -
Nonstop2h 59m
Tue 13/1019:50 -
Nonstop2h 34m
Deal found 15/9£170
Fri 23/1006:00 -
Nonstop2h 59m
Mon 26/1018:00 -
Nonstop2h 30m
Deal found 14/9£171
Wed 14/1006:00 -
Nonstop2h 59m
Thu 15/1021:24 -
Nonstop2h 30m
Deal found 17/9£171
Thu 15/1016:11 -
1 stop6h 59m
Tue 20/1006:10 -
1 stop7h 19m
Deal found 17/9£172
Mon 19/1008:05 -
Nonstop2h 55m
Wed 21/1018:24 -
Nonstop2h 35m
Deal found 16/9£173
Sat 10/1019:40 -
Nonstop2h 51m
Tue 13/1017:29 -
1 stop5h 30m
Deal found 15/9£174
Best flights from Boston to O'Hare Intl
Discover carefully curated flight deals from Boston to O'Hare Intl that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 17 September 2026.
Wed 23/1205:45 -
Nonstop3h 06m
Wed 30/1221:49 -
Nonstop2h 29m
Deal found 17/9£172
Thu 1/1014:59 -
1 stop5h 16m
Mon 5/1007:35 -
Nonstop2h 33m
Deal found 15/9£188
Fri 2/1007:00 -
Nonstop2h 48m
Mon 5/1007:00 -
1 stop6h 29m
Deal found 14/9£191
Mon 5/1010:29 -
Nonstop3h 04m
Wed 7/1020:00 -
Nonstop2h 36m
Deal found 14/9£221
Mon 12/1007:01 -
Nonstop2h 59m
Wed 14/1006:00 -
1 stop4h 24m
Deal found 15/9£180
Sun 4/1005:45 -
1 stop4h 53m
Sat 10/1021:24 -
Nonstop2h 30m
Deal found 15/9£188
Thu 11/316:10 -
Nonstop3h 00m
Tue 16/309:30 -
1 stop6h 11m
Deal found 17/9£228
Sun 1/1107:31 -
Nonstop3h 03m
Sun 8/1121:20 -
Nonstop2h 26m
Deal found 17/9£200
Mon 12/1007:30 -
Nonstop2h 54m
Mon 26/1006:00 -
1 stop7h 25m
Deal found 16/9£235
Thu 5/1106:00 -
2 stops8h 04m
Sun 8/1105:00 -
1 stop5h 07m
Deal found 17/9£220
Thu 1/1020:30 -
Nonstop2h 59m
Sun 4/1007:29 -
Nonstop2h 31m
Deal found 16/9£221
Wed 11/1106:00 -
1 stop5h 48m
Sun 15/1106:15 -
Nonstop2h 19m
Deal found 17/9£224
Direct flights from Boston to O'Hare Intl
Explore direct flight options from Boston to O'Hare Intl based on user searches, and compare prices and availability for your desired travel dates. Data last updated 17 September 2026.
Tue 3/1119:10 -
Nonstop2h 56m
Wed 4/1107:25 -
Nonstop2h 35m
Deal found 16/9£164
Mon 12/1006:00 -
Nonstop2h 59m
Fri 16/1021:24 -
Nonstop2h 30m
Deal found 15/9£166
Sat 10/1019:40 -
Nonstop2h 51m
Sat 24/1007:25 -
Nonstop2h 35m
Deal found 15/9£167
Wed 7/1006:00 -
Nonstop2h 59m
Fri 9/1021:24 -
Nonstop2h 30m
Deal found 15/9£168
Thu 8/1006:00 -
Nonstop2h 59m
Tue 13/1019:50 -
Nonstop2h 34m
Deal found 15/9£170
Fri 23/1006:00 -
Nonstop2h 59m
Mon 26/1018:00 -
Nonstop2h 30m
Deal found 14/9£171
Wed 14/1006:00 -
Nonstop2h 59m
Thu 15/1021:24 -
Nonstop2h 30m
Deal found 17/9£171
Tue 20/1009:23 -
Nonstop2h 52m
Tue 27/1009:13 -
Nonstop2h 33m
Deal found 17/9£172
Thu 8/1006:00 -
Nonstop2h 59m
Sun 11/1006:10 -
Nonstop2h 23m
Deal found 16/9£173
Sat 17/1007:01 -
Nonstop2h 59m
Sun 25/1006:59 -
Nonstop2h 19m
Deal found 17/9£175
Thu 22/1019:40 -
Nonstop2h 51m
Mon 26/1010:24 -
Nonstop2h 30m
Deal found 17/9£176
Fri 20/1114:40 -
Nonstop3h 00m
Mon 23/1111:00 -
Nonstop2h 24m
Deal found 16/9£177
Last-minute flights from Boston to O'Hare Intl
Discover last-minute flight deals from Boston to O'Hare Intl. Data last updated 17 September 2026 and is based on user searches.
Thu 1/1007:00 -
Nonstop2h 48m
Mon 5/1007:00 -
1 stop6h 29m
Deal found 17/9£162
Mon 5/1016:10 -
1 stop6h 50m
Tue 6/1007:05 -
1 stop6h 24m
Deal found 14/9£165
Mon 5/1009:10 -
1 stop4h 49m
Wed 7/1010:05 -
1 stop7h 23m
Deal found 16/9£166
Thu 8/1006:00 -
Nonstop2h 59m
Tue 13/1019:50 -
Nonstop2h 34m
Deal found 15/9£170
Sat 10/1019:40 -
Nonstop2h 51m
Sat 24/1007:25 -
Nonstop2h 35m
Deal found 15/9£167
Sat 10/1019:40 -
Nonstop2h 51m
Tue 13/1017:29 -
1 stop5h 30m
Deal found 15/9£174
Wed 14/1006:00 -
Nonstop2h 59m
Thu 15/1021:24 -
Nonstop2h 30m
Deal found 17/9£171
Thu 15/1016:11 -
1 stop6h 59m
Mon 19/1006:10 -
1 stop7h 19m
Deal found 17/9£168
Sat 17/1007:01 -
Nonstop2h 59m
Sun 25/1006:59 -
Nonstop2h 19m
Deal found 17/9£175
Mon 19/1008:05 -
Nonstop2h 55m
Wed 21/1018:24 -
Nonstop2h 35m
Deal found 16/9£173
Fri 23/1006:00 -
Nonstop2h 59m
Mon 26/1018:00 -
Nonstop2h 30m
Deal found 14/9£171
One-way flights from Boston to O'Hare Intl
Search for one-way flight options from Boston to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated 17 September 2026.
Thu 24/1205:45 -
Nonstop3h 06m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£87
Thu 22/1006:00 -
Nonstop2h 59m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£88
Thu 17/1210:00 -
1 stop8h 04m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 16/9£88
Mon 5/1007:30 -
Nonstop2h 54m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 14/9£90
Mon 12/1006:00 -
Nonstop2h 59m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 15/9£90
Fri 25/1215:31 -
1 stop7h 44m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£91
Tue 13/1005:45 -
1 stop4h 53m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£95
Sun 1/1105:30 -
1 stop5h 15m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£96
Mon 21/1219:40 -
1 stop4h 59m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 17/9£96
Thu 8/1006:00 -
Nonstop2h 59m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 15/9£99
Wed 21/1008:05 -
Nonstop2h 55m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 16/9£101
Find flight deals from Boston to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to O'Hare Intl (ORD). 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 17 September 2026.
Customise your flight search to find flights from Boston to O'Hare Intl 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 17 September 2026.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport 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
Thu 22/10
05:39-10:29
1 stop5h 50m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£88
Fastest return journey
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 12/3
20:10-22:04
Nonstop2h 54m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£111
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 17/1
06:00-13:08
2 stops8h 08m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£112
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 14/10
06:00-14:42
2 stops9h 42m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£112
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 11/11
06:00-14:54
2 stops9h 54m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£112
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 29/9
07:30-09:24
Nonstop2h 54m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£114
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 25/12
05:30-12:11
1 stop7h 41m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£118
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 4/10
05:45-09:38
1 stop4h 53m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£118
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 1/10
13:10-16:13
1 stop4h 03m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£118
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 24/11
06:00-10:30
1 stop5h 30m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£118
Flights are sorted by cheapest return flights first.
Deals found on 15/9
Showing 1-10 of 23 resultsSorted by cheapest first
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2
3
Best time to book a flight from Boston to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Boston with our price prediction graph.
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 O'Hare Intl Airport
Prices
Airlines
Delays
How far ahead should I book a flight from Boston to Chicago O'Hare Intl Airport?
The best time to book flights from Boston to Chicago O'Hare Intl Airport is 77 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.
What is the cheapest month to book a flight from Boston to Chicago O'Hare Intl Airport?
Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of £147). Flying from Boston to Chicago O'Hare Intl Airport in October is currently the most expensive (average of £213). 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 ORD?
Find hourly flight availability from Boston to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 17 September 2026.
When flying from Boston to Chicago O'Hare Intl Airport, 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 66% versus a flight in the afternoon.
How much does it cost for a return flight from Boston to Chicago O'Hare Intl Airport?
Airfare is typical for this route at the moment.
Boston to Chicago O'Hare Intl Airport flights typically cost between £160 and £262 in October.The cheapest return price found within the last 5 days was £162 on JetBlue (1 Oct–5 Oct).
Weekly flight availability from Boston to Chicago O'Hare Intl Airport
Explore weekly flight availability from Boston to O'Hare Intl. 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 17 September 2026.
The most flights from BOS to ORD are scheduled on a Wednesday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).
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 172 minutes.
What is the most punctual flight time for Boston to Chicago flights?
Historically, flights departing at night 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.
Related info for your journey
Find useful and relevant information for your journey from Boston to O'Hare Intl. 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 O'Hare Intl?
If you book a flight to Chicago O'Hare Intl from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 44 flights from Logan Intl to Chicago O'Hare Intl per day from 0 different airlines.
How long is the flight from Boston to Chicago O'Hare Intl Airport?
United Airlines can get you from Boston to Chicago O'Hare Intl Airport in just under 4h 53m. Your travel time can differ by up to . The distance from Boston to Chicago O'Hare Intl Airport is about 864 mi.
What are the most reliable airlines from Boston to Chicago O'Hare Intl Airport?
No one likes to see their flight delayed. When booking a flight from Boston to Chicago O'Hare Intl Airport consider choosing Japan Airlines (83%), Cathay Pacific (74%) or ANA (73%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Boston to Chicago O'Hare Intl Airport?
While on average a flight from Boston to Chicago O'Hare Intl Airport is generally £232, our data shows the cheapest flight currently is £78. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £220 for that flight.
Can I find deals for business class flights from Boston to O'Hare Intl?
Yes. Cheapflights offers flight deals from Boston to O'Hare Intl 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 O'Hare Intl Airport?
Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of £147). Flying from Boston to Chicago O'Hare Intl Airport in October is currently the most expensive (average of £213). 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 O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 17 September 2026.
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on 17 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 Boston to O'Hare Intl?
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Boston to O'Hare Intl. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Why should you use Cheapflights to find cheap flight tickets from Boston to O'Hare Intl?
Cheapflights simply makes it quick and affordable to book flights from Boston to O'Hare Intl by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Boston to O'Hare Intl with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to O'Hare Intl flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Boston to O'Hare Intl become cheaper?
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to O'Hare Intl from Boston today and book when prices fit your budget.
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