Cheap flights from Boston to Chicago O'Hare Intl Airport from £92
This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 21/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
4 Dec — 11 Dec1
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 69 days in advance, depart on a Wednesday or Friday and return on a Thursday
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 4 November 2026.
Thu 19/1107:55 -
Nonstop3h 04m
Fri 20/1117:30 -
Nonstop2h 29m
Deal found 4/11£184
Thu 19/1114:40 -
Nonstop3h 00m
Mon 23/1117:30 -
Nonstop2h 29m
Deal found 4/11£185
Sat 21/1114:40 -
Nonstop3h 00m
Wed 25/1117:30 -
Nonstop2h 29m
Deal found 4/11£209
Sun 20/1216:45 -
Nonstop3h 13m
Thu 24/1219:55 -
Nonstop2h 26m
Deal found 4/11£209
Thu 19/1120:40 -
Nonstop2h 56m
Sun 22/1107:05 -
Nonstop2h 27m
Deal found 3/11£214
Wed 18/1109:59 -
Nonstop3h 01m
Mon 23/1117:30 -
Nonstop2h 29m
Deal found 4/11£217
Wed 18/1109:59 -
Nonstop3h 01m
Fri 20/1117:30 -
Nonstop2h 29m
Deal found 4/11£218
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 4 November 2026.
Fri 20/1110:42 -
Nonstop3h 04m
Sun 22/1118:00 -
Nonstop2h 30m
Deal found 31/10£214
Tue 15/1220:59 -
Nonstop2h 58m
Tue 22/1207:05 -
Nonstop2h 28m
Deal found 31/10£224
Sat 26/1205:30 -
1 stop5h 19m
Fri 1/108:05 -
Nonstop2h 33m
Deal found 30/10£229
Wed 6/106:00 -
Nonstop3h 00m
Wed 6/114:40 -
Nonstop2h 29m
Deal found 3/11£233
Wed 30/1205:30 -
1 stop5h 19m
Sat 2/107:05 -
Nonstop2h 28m
Deal found 2/11£229
Sun 22/1109:00 -
1 stop5h 09m
Mon 30/1121:20 -
Nonstop2h 25m
Deal found 1/11£239
Fri 20/1107:30 -
Nonstop3h 05m
Thu 3/1217:02 -
1 stop5h 56m
Deal found 30/10£231
Thu 26/1113:35 -
Nonstop2h 55m
Tue 1/1207:05 -
Nonstop2h 31m
Deal found 3/11£233
Tue 19/120:30 -
Nonstop3h 01m
Fri 22/110:05 -
1 stop7h 20m
Deal found 30/10£241
Tue 29/1205:30 -
1 stop5h 19m
Sun 3/117:55 -
1 stop5h 04m
Deal found 3/11£244
Sun 27/1205:30 -
1 stop5h 19m
Sun 3/117:55 -
1 stop5h 04m
Deal found 1/11£244
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 4 November 2026.
Thu 19/1107:55 -
Nonstop3h 04m
Sat 21/1117:30 -
Nonstop2h 29m
Deal found 4/11£184
Thu 19/1114:40 -
Nonstop3h 00m
Mon 23/1117:30 -
Nonstop2h 29m
Deal found 4/11£185
Sat 21/1107:55 -
Nonstop3h 04m
Thu 26/1111:00 -
Nonstop2h 24m
Deal found 4/11£209
Thu 19/1114:40 -
Nonstop3h 00m
Fri 20/1111:00 -
Nonstop2h 24m
Deal found 4/11£213
Thu 19/1120:40 -
Nonstop2h 56m
Sun 22/1107:05 -
Nonstop2h 27m
Deal found 3/11£214
Wed 18/1109:59 -
Nonstop3h 01m
Sat 21/1117:30 -
Nonstop2h 29m
Deal found 4/11£217
Wed 18/1109:59 -
Nonstop3h 01m
Fri 20/1117:30 -
Nonstop2h 29m
Deal found 4/11£218
Thu 24/1205:45 -
Nonstop3h 06m
Tue 29/1221:49 -
Nonstop2h 29m
Deal found 1/11£218
Thu 19/1116:35 -
Nonstop3h 09m
Fri 20/1107:05 -
Nonstop2h 27m
Deal found 3/11£221
Last-minute flights from Boston to O'Hare Intl
Discover last-minute flight deals from Boston to O'Hare Intl. Data last updated 4 November 2026 and is based on user searches.
Thu 12/1116:56 -
Nonstop3h 02m
Sat 21/1121:20 -
Nonstop2h 26m
Deal found 2/11£262
Thu 12/1106:05 -
1 stop7h 41m
Sat 21/1116:40 -
Nonstop2h 23m
Deal found 2/11£270
Fri 13/1115:01 -
Nonstop3h 04m
Sun 15/1107:00 -
Nonstop2h 19m
Deal found 30/10£250
Fri 13/1105:30 -
1 stop6h 09m
Mon 16/1107:05 -
Nonstop2h 27m
Deal found 31/10£257
Fri 13/1107:30 -
Nonstop3h 05m
Wed 18/1115:05 -
Nonstop2h 24m
Deal found 3/11£280
Fri 13/1107:15 -
1 stop5h 33m
Mon 4/110:05 -
1 stop5h 16m
Deal found 31/10£285
Sat 14/1109:59 -
Nonstop3h 01m
Sat 21/1117:30 -
Nonstop2h 29m
Deal found 4/11£247
Sat 14/1106:45 -
1 stop6h 35m
Sat 14/1117:42 -
1 stop5h 02m
Deal found 30/10£265
Sat 14/1109:59 -
Nonstop3h 01m
Fri 20/1111:00 -
Nonstop2h 24m
Deal found 4/11£277
Sat 14/1110:10 -
1 stop5h 42m
Sat 21/1107:05 -
Nonstop2h 27m
Deal found 3/11£277
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 4 November 2026.
Sat 21/1114:40 -
Nonstop3h 00m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 3/11£92
Mon 16/1112:39 -
1 stop7h 06m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 2/11£96
Fri 18/1205:45 -
Nonstop3h 06m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 4/11£107
Sun 20/1210:25 -
1 stop15h 31m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 3/11£110
Fri 18/1220:59 -
Nonstop3h 01m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 4/11£111
Mon 21/1205:45 -
1 stop6h 52m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 1/11£115
Thu 26/1109:12 -
Nonstop3h 03m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 3/11£117
Thu 24/1205:45 -
Nonstop3h 06m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 3/11£119
Sat 5/1215:42 -
1 stop6h 51m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 1/11£121
Sun 27/1205:30 -
1 stop5h 19m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 3/11£122
Tue 1/1213:05 -
1 stop6h 21m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 4/11£124
Mon 30/1120:25 -
Nonstop3h 04m
Wed 31/1200:00 -
Nonstop0h 00m
Deal found 3/11£125
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 4 November 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 4 November 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
Fri 18/12
05:45-07:51
Nonstop3h 06m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£107
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 16/2
20:20-22:27
Nonstop3h 07m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 8/1
11:52-14:00
Nonstop3h 08m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 21/12
13:04-16:53
1 stop4h 49m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£122
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 26/12
05:30-09:49
1 stop5h 19m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£122
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
£124
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 27/11
05:30-10:39
1 stop6h 09m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£124
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 16/11
17:05-19:17
Nonstop3h 12m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£125
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 27/12
05:45-07:51
Nonstop3h 06m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£125
Fastest return journey
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 20/4
20:10-22:04
Nonstop2h 54m
Chicago O'Hare Intl
Wed 31/12
00:00-01:00
Nonstop0h 00m
£125
Flights are sorted by cheapest return flights first.
Deals found on 4/11
Showing 1-10 of 22 resultsSorted by cheapest first
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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 90 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 £148). Flying from Boston to Chicago O'Hare Intl Airport in October is currently the most expensive (average of £269). 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 4 November 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 65% versus a flight at midday.
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 £168 and £318 in November.The cheapest return price found within the last 5 days was £184 on JetBlue (19 Nov–20 Nov).
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 4 November 2026.
The most flights from BOS to ORD are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 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 Monday 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 9% 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 46 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 and Delta can get you from Boston to Chicago O'Hare Intl Airport in just under 2h 58m. Your travel time will be generally consistent. The distance from Boston to Chicago O'Hare Intl Airport is about 864 mi. All flights are typically direct.
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 Envoy Air (86%), Japan Airlines (83%) or Cathay Pacific (75%) as they are the most reliable in getting you off to your destination on time.
Can I find deals for flights from Boston to O'Hare Intl that include hotel bookings?
Yes. In addition to deals on Boston to O'Hare Intl flights, Cheapflights offers holiday packages that include both flights and hotel.
How can I find direct flights from Boston to O'Hare Intl?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to O'Hare Intl.
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 £148). Flying from Boston to Chicago O'Hare Intl Airport in October is currently the most expensive (average of £269). 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 4 November 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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