$88+ Cheap flights from O'Hare Intl (ORD) to Boston (BOS)
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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Sep 8 — Sep 151
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Boston with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in January or September, booked 65 days in advance, depart on a Saturday or Thursday and return on a Friday
Cheap flight deals from O'Hare Intl to Boston
Cheapest
Best
Last-minute
One-way
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 August 9, 2026.
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 August 9, 2026.
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/4![Frontier logo]()
$166
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/4![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop14h 10m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/4![Frontier logo]()
$182
This CheapTickets deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Sat 9/2612:54 pm -
1 stop6h 29m
Deal found 8/5![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:33 pm -
1 stop12h 19m
Wed 10/2111:28 am -
1 stop10h 00m
Deal found 8/6![Frontier logo]()
$186
This Priceline deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:24 pm -
Nonstop2h 45m
Thu 9/1012:54 pm -
1 stop6h 29m
Deal found 8/4![Multiple Airlines logo]()
$187
This Trip.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/8![Frontier logo]()
$188
This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Fri 9/1811:36 am -
1 stop12h 23m
Deal found 8/5![Frontier logo]()
$190
Best flights from O'Hare Intl to BostonDiscover carefully curated flight deals from O'Hare Intl to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
Discover carefully curated flight deals from O'Hare Intl to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 9, 2026.
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:40 pm -
Nonstop2h 41m
Tue 10/137:40 pm -
Nonstop2h 51m
Deal found 8/4![Delta logo]()
$207
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:38 am -
Nonstop2h 28m
Wed 10/215:00 pm -
Nonstop3h 22m
Deal found 8/6![JetBlue logo]()
$231
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:10 am -
Nonstop2h 24m
Sat 10/245:45 am -
1 stop4h 52m
Deal found 8/7![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:05 pm -
Nonstop2h 39m
Tue 11/31:35 pm -
Nonstop2h 52m
Deal found 8/8![Delta logo]()
$236
This JetBlue deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:20 pm -
Nonstop2h 31m
Sun 9/68:10 am -
Nonstop2h 56m
Deal found 8/8![JetBlue logo]()
$250
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:35 pm -
Nonstop2h 44m
Thu 9/248:31 pm -
Nonstop2h 58m
Deal found 8/7![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:30 pm -
Nonstop2h 30m
Sun 9/612:25 pm -
Nonstop2h 54m
Deal found 8/8![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:24 pm -
Nonstop2h 35m
Fri 9/410:38 am -
Nonstop2h 51m
Deal found 8/7![United Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:38 am -
Nonstop2h 28m
Sun 10/255:35 am -
1 stop9h 04m
Deal found 8/8![JetBlue logo]()
$258
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:24 pm -
Nonstop2h 30m
Mon 9/287:55 am -
Nonstop2h 56m
Deal found 8/7![United Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:38 am -
Nonstop2h 28m
Mon 10/263:59 pm -
1 stop8h 45m
Deal found 8/5![JetBlue logo]()
$260
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:10 am -
Nonstop2h 23m
Fri 10/26:43 pm -
Nonstop2h 57m
Deal found 8/8![United Airlines logo]()
$255
Last-minute flights from O'Hare Intl to BostonDiscover last-minute flight deals from O'Hare Intl to Boston. Data last updated August 9, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Boston. Data last updated August 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop14h 10m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/4![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Fri 9/1112:54 pm -
1 stop6h 29m
Deal found 8/8![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/8![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/4![Frontier logo]()
$166
This Priceline deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:24 pm -
Nonstop2h 45m
Thu 9/1012:54 pm -
1 stop6h 29m
Deal found 8/4![Multiple Airlines logo]()
$187
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/4![Frontier logo]()
$172
This Trip.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Fri 9/1811:36 am -
1 stop12h 23m
Deal found 8/5![Frontier logo]()
$190
This CheapTickets deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Sat 9/2612:54 pm -
1 stop6h 29m
Deal found 8/5![Frontier logo]()
$185
One-way flights from O'Hare Intl to BostonSearch for one-way flight options from O'Hare Intl to Boston. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
Search for one-way flight options from O'Hare Intl to Boston. Find affordable one-way fares based on user searches. Data last updated August 9, 2026.
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/4![Frontier logo]()
$88
This Trip.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/4![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/5![Frontier logo]()
$93
This Frontier deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:33 pm -
1 stop12h 19m
Deal found 8/6![Frontier logo]()
$95
This Jetabroad deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:50 pm -
1 stop18h 01m
Deal found 8/5![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm -
1 stop18h 01m
Deal found 8/4![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:33 pm -
1 stop12h 19m
Deal found 8/4![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/7![Frontier logo]()
$100
This Trip.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/4![Frontier logo]()
$101
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 August 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Frontier) |
One-way from | $88 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $251 |
Good round-trip deal | $221 or less |
Good one-way deal | $143 or less |
Cheapflights Fare Finder
Customize 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 2,558,603 searches. Data last updated August 9, 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
Cheapest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/10
4:40 pm-8:21 pm
Nonstop2h 41m
Boston Logan Intl
Tue 10/13
7:40 pm-9:31 pm
Nonstop2h 51m
$207
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/15
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Wed 10/21
5:00 pm-7:22 pm
Nonstop3h 22m
$231
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 10/30
3:05 pm-6:44 pm
Nonstop2h 39m
Boston Logan Intl
Tue 11/3
1:35 pm-3:27 pm
Nonstop2h 52m
$236
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/17
6:10 am-9:34 am
Nonstop2h 24m
Boston Logan Intl
Sat 10/24
5:45 am-9:37 am
1 stop4h 52m
$237
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 8/24
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Sun 9/6
8:10 am-10:06 am
Nonstop2h 56m
$250
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 8/26
7:30 pm-11:00 pm
Nonstop2h 30m
Boston Logan Intl
Sun 9/6
12:25 pm-2:19 pm
Nonstop2h 54m
$250
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 9/21
3:35 pm-7:19 pm
Nonstop2h 44m
Boston Logan Intl
Thu 9/24
8:31 pm-10:29 pm
Nonstop2h 58m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 9/1
6:24 pm-9:59 pm
Nonstop2h 35m
Boston Logan Intl
Fri 9/4
10:38 am-12:29 pm
Nonstop2h 51m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/25
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Mon 9/28
7:55 am-9:51 am
Nonstop2h 56m
$255
Quickest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/1
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Fri 10/2
6:43 pm-8:40 pm
Nonstop2h 57m
$255
Showing 1-10 of 24 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl to Boston
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Boston in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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 round-trip 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 64 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 $205). Flying from Chicago O'Hare Intl Airport to Boston in June is currently the most expensive (average of $290). 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 August 9, 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 23% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Boston?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Boston. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to Boston delayed?
About 25% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 154 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 last year, Delta have had the lowest number of delays on this route, with just 21% of flights being delayed.
The best insider tips for Chicago O'Hare Intl Airport to Boston flights
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Cheapflights partnered with top experts to bring you the best recommendations for your Chicago O'Hare Intl Airport to Boston trip
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Reviews of airlines servicing Boston
Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated August 9, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Boston to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
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.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Cambridge
Concord
Brockton
Seekonk
Cranston
Dedham
Warwick
Peabody
Hampton Beach
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Revere
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O'Hare Intl and Boston flights
Browse other O'Hare Intl and Boston flight options. Last updated on August 9, 2026.
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Top 4 airlines flying from O'Hare Intl to Boston
Discover the top 4 airlines that operate flights from O'Hare Intl to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$181 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$239 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$282 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$252 | FlexibilityNo cancel fee | On-time71% |