Cheap flights from Chicago O'Hare Intl Airport to Boston from £48
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 17/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
11 Jan — 18 Jan1
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 September, booked 72 days in advance, depart on a Tuesday or Thursday and return on a Wednesday
Cheap flight deals from O'Hare Intl to Boston
Enter your travel dates to find the best prices.
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 12 December 2025.
Sat 13/1216:05ORD - BOS
Nonstop2h 20mUnited Airlines
Sun 14/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/12£102
Thu 25/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Wed 31/1206:01BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/12£114
Sun 14/1209:19ORD - BOS
Nonstop2h 24mUnited Airlines
Tue 16/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/12£117
Thu 18/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Sun 21/1219:44BOS - ORD
1 stop5h 00mUnited Airlines
Deal found 11/12£125
Tue 23/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Wed 31/1206:01BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/12£126
Mon 15/1211:00ORD - BOS
Nonstop2h 20mUnited Airlines
Thu 18/1207:45BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/12£132
Sat 20/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Tue 30/1206:01BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/12£133
Tue 16/1218:17ORD - BOS
Nonstop2h 28mUnited Airlines
Wed 17/1205:30BOS - ORD
1 stop5h 06mUnited Airlines
Deal found 10/12£136
Mon 29/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Sun 4/106:01BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/12£137
Thu 18/1213:55ORD - BOS
Nonstop2h 22mUnited Airlines
Thu 25/1205:20BOS - ORD
1 stop5h 18mUnited Airlines
Deal found 10/12£140
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 12 December 2025.
Sat 17/107:05ORD - BOS
Nonstop2h 35mDelta
Sun 18/107:30BOS - ORD
Nonstop3h 11mDelta
Deal found 11/12£95
Sat 31/107:45ORD - BOS
Nonstop2h 25mJetBlue
Sun 1/215:20BOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/12£102
Tue 3/209:13ORD - BOS
Nonstop2h 33mUnited Airlines
Tue 3/216:49BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/12£102
Fri 30/118:59ORD - BOS
Nonstop2h 32mDelta
Sat 31/107:30BOS - ORD
Nonstop3h 11mDelta
Deal found 10/12£102
Tue 17/210:00ORD - BOS
Nonstop2h 23mJetBlue
Sat 21/207:00BOS - ORD
Nonstop3h 10mJetBlue
Deal found 9/12£102
Fri 23/107:30ORD - BOS
Nonstop2h 22mUnited Airlines
Mon 26/116:16BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 9/12£102
Fri 27/206:04ORD - BOS
1 stop7h 10mJetBlue
Sun 1/307:00BOS - ORD
Nonstop3h 10mJetBlue
Deal found 10/12£114
Sat 10/114:00ORD - BOS
Nonstop2h 29mDelta
Sun 11/119:55BOS - ORD
Nonstop3h 06mDelta
Deal found 11/12£117
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 12 December 2025.
Sat 17/109:13ORD - BOS
Nonstop2h 33mUnited Airlines
Sun 18/106:00BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/12£95
Sat 17/107:05ORD - BOS
Nonstop2h 35mDelta
Sun 18/107:30BOS - ORD
Nonstop3h 11mDelta
Deal found 11/12£96
Sat 17/107:45ORD - BOS
Nonstop2h 25mJetBlue
Sun 18/115:35BOS - ORD
Nonstop3h 08mJetBlue
Deal found 10/12£99
Sat 24/107:45ORD - BOS
Nonstop2h 25mJetBlue
Sat 31/115:35BOS - ORD
Nonstop3h 08mJetBlue
Deal found 10/12£101
Sat 18/418:26ORD - BOS
Nonstop2h 25mJetBlue
Wed 22/408:50BOS - ORD
Nonstop2h 54mJetBlue
Deal found 10/12£102
Fri 9/116:15ORD - BOS
Nonstop2h 24mUnited Airlines
Fri 16/106:00BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/12£111
Fri 6/321:10ORD - BOS
Nonstop2h 20mUnited Airlines
Thu 12/306:00BOS - ORD
Nonstop3h 05mUnited Airlines
Deal found 9/12£111
Thu 25/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Wed 31/1206:01BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/12£114
Sun 18/107:05ORD - BOS
Nonstop2h 35mDelta
Fri 23/107:30BOS - ORD
Nonstop3h 11mDelta
Deal found 11/12£117
Fri 27/216:15ORD - BOS
Nonstop2h 22mUnited Airlines
Sun 1/306:00BOS - ORD
Nonstop3h 05mUnited Airlines
Deal found 10/12£118
Wed 14/109:13ORD - BOS
Nonstop2h 33mUnited Airlines
Mon 19/109:30BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/12£119
Last-minute flights from O'Hare Intl to Boston
Discover last-minute flight deals from O'Hare Intl to Boston. Data last updated 12 December 2025 and is based on user searches.
Fri 9/116:15ORD - BOS
Nonstop2h 24mUnited Airlines
Fri 16/106:00BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/12£111
Wed 14/107:05ORD - BOS
Nonstop2h 35mDelta
Fri 23/120:25BOS - ORD
Nonstop3h 04mDelta
Deal found 11/12£102
Wed 14/109:40ORD - BOS
1 stop4h 54mJetBlue
Tue 20/115:35BOS - ORD
Nonstop3h 08mJetBlue
Deal found 11/12£110
Wed 14/109:40ORD - BOS
1 stop4h 54mJetBlue
Fri 23/115:35BOS - ORD
Nonstop3h 08mJetBlue
Deal found 11/12£114
Thu 15/107:20ORD - BOS
1 stop8h 08mSpirit Airlines
Fri 23/107:00BOS - ORD
1 stop11h 52mSpirit Airlines
Deal found 11/12£102
Sat 17/114:00ORD - BOS
Nonstop2h 24mUnited Airlines
Tue 20/116:49BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 9/12£95
Sat 17/107:05ORD - BOS
Nonstop2h 35mDelta
Sun 18/107:30BOS - ORD
Nonstop3h 11mDelta
Deal found 11/12£96
Sat 17/107:45ORD - BOS
Nonstop2h 25mJetBlue
Sun 18/115:35BOS - ORD
Nonstop3h 08mJetBlue
Deal found 10/12£99
Sat 17/107:45ORD - BOS
Nonstop2h 25mJetBlue
Sat 17/113:40BOS - ORD
1 stop6h 56mJetBlue
Deal found 11/12£106
Sat 24/107:20ORD - BOS
1 stop8h 08mSpirit Airlines
Sat 31/107:00BOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 10/12£97
Sat 24/107:45ORD - BOS
Nonstop2h 25mJetBlue
Sat 31/115:35BOS - ORD
Nonstop3h 08mJetBlue
Deal found 10/12£101
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 12 December 2025.
Sat 17/107:05ORD - BOS
Nonstop2h 35mDelta
Deal found 10/12£48
Sat 10/114:00ORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 10/12£52
Wed 7/109:13ORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/12£55
Tue 16/1216:05ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 10/12£59
Mon 19/116:15ORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 10/12£60
Thu 5/209:40ORD - BOS
1 stop6h 33mJetBlue
Deal found 10/12£63
Thu 19/209:17ORD - BOS
Nonstop2h 29mUnited Airlines
Deal found 11/12£64
Tue 16/1213:45ORD - BOS
1 stop7h 30mSouthwest
Deal found 10/12£66
Sun 15/206:04ORD - BOS
1 stop7h 20mJetBlue
Deal found 10/12£69
Mon 23/216:15ORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 11/12£72
Fri 19/1207:45ORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 11/12£72
Fri 16/107:30ORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 11/12£73
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 12 December 2025.
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 858,174 searches. Data last updated 12 December 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Boston that are best for you.
Fly from
O'Hare Intl
Fly to
Boston
Route
Depart
Return
Price
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 17/1
07:05-10:40
Nonstop2h 35m
Boston Logan Intl
Sun 18/1
07:30-09:41
Nonstop3h 11m
£95
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 31/1
07:45-11:10
Nonstop2h 25m
Boston Logan Intl
Sun 1/2
15:20-17:25
Nonstop3h 05m
£102
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 3/2
09:13-12:46
Nonstop2h 33m
Boston Logan Intl
Tue 3/2
16:49-18:49
Nonstop3h 00m
£102
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 30/1
18:59-22:31
Nonstop2h 32m
Boston Logan Intl
Sat 31/1
07:30-09:41
Nonstop3h 11m
£102
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 17/2
10:00-13:23
Nonstop2h 23m
Boston Logan Intl
Sat 21/2
07:00-09:10
Nonstop3h 10m
£102
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 23/1
07:30-10:52
Nonstop2h 22m
Boston Logan Intl
Mon 26/1
16:16-18:16
Nonstop3h 00m
£102
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 27/2
06:04-14:14
1 stop7h 10m
Boston Logan Intl
Sun 1/3
07:00-09:10
Nonstop3h 10m
£114
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 10/1
14:00-17:29
Nonstop2h 29m
Boston Logan Intl
Sun 11/1
19:55-22:01
Nonstop3h 06m
£117
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 17/1
10:35-14:00
Nonstop2h 25m
£48
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 10/1
14:00-17:29
Nonstop2h 29m
£52
Flights are sorted by cheapest return flights first.
Deals found on 11/12
Showing 1-10 of 19 results
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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.
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?
Use this chart to determine the optimal time to book a return flight from O'Hare Intl to Boston. Price data was last updated on 5 December 2025.
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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £66). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of £102). 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 12 December 2025.
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 86% on your trip compared to booking a flight at midday.
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 12 December 2025.
The most flights from ORD to BOS are scheduled on a Friday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).
How often are flights from Chicago to Boston delayed?
About 22% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 152 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, JetBlue have had the lowest number of delays on this route, with just 18% 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 54 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 £102, Delta can have you in Boston from Chicago O'Hare Intl Airport in 2h 25m. There are 864 mi between Chicago O'Hare Intl Airport and Boston. Most flights are nonstop.
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 (79%), JetBlue (76%), Hawaiian Airlines (76%).
What are the cheapest flights from Chicago O'Hare Intl Airport to Boston?
Looking at all options, your cheapest flight can be booked for £44. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for £117 on average, our data indicates £354 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 £66). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of £102). 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
Cambridge
Peabody
Somerville
Quincy
Waltham
Chelmsford
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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 12 December 2025.
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on 12 December 2025.
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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