$103+ Cheap flights from Boston (BOS) to O'Hare Intl (ORD)
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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Sep 19 — Sep 261
Round-trip
1 adult, Economy
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Find cheap flights from Boston to O'Hare Intl 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 Boston Logan Intl to Chicago O'Hare Intl are usually found in January or February, booked 44 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Boston to O'Hare Intl
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to O'Hare IntlExplore 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 August 20, 2026.
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 August 20, 2026.
This Frontier deal was found by Cheapflights users on 8/17. 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.
Tue 9/112:45 pm -
1 stop8h 23m
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/17![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/18. 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 9/212:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 8/16. 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 9/212:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$183
This Trip.com deal was found by Cheapflights users on 8/17. 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 9/512:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/17![Frontier logo]()
$184
This CheapOair deal was found by Cheapflights users on 8/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:17 am -
1 stop12h 42m
Sun 10/43:50 pm -
1 stop18h 01m
Deal found 8/16![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/16. 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 9/1212:54 pm -
1 stop6h 29m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 8/15. 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.
Thu 10/111:17 am -
1 stop12h 42m
Fri 10/98:11 pm -
1 stop13h 51m
Deal found 8/15![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:45 pm -
1 stop8h 14m
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:45 pm -
1 stop8h 14m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/15![Frontier logo]()
$194
Best flights from Boston to O'Hare IntlDiscover carefully curated flight deals from Boston to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
Discover carefully curated flight deals from Boston to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
This Delta deal was found by Cheapflights users on 8/17. 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.
Thu 10/14:30 pm -
Nonstop2h 58m
Thu 10/87:25 am -
Nonstop2h 35m
Deal found 8/17![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/18. 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 10/88:30 pm -
Nonstop2h 59m
Sun 10/119:24 pm -
Nonstop2h 30m
Deal found 8/18![United Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/19. 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.
Sun 9/207:00 am -
Nonstop2h 48m
Fri 9/258:24 pm -
Nonstop2h 45m
Deal found 8/19![JetBlue logo]()
$275
This Delta deal was found by Cheapflights users on 8/15. 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.
Mon 9/288:50 pm -
Nonstop2h 42m
Fri 10/23:05 pm -
Nonstop2h 47m
Deal found 8/15![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/16. 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 10/86:00 am -
Nonstop2h 59m
Fri 10/99:24 pm -
Nonstop2h 30m
Deal found 8/16![United Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 8/19. 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.
Mon 9/148:50 pm -
Nonstop2h 42m
Fri 9/183:05 pm -
Nonstop2h 47m
Deal found 8/19![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 8/16. 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 10/27:30 am -
Nonstop2h 54m
Sun 10/47:35 am -
Nonstop2h 33m
Deal found 8/16![Delta logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/17. 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 9/112:45 pm -
1 stop9h 23m
Sun 9/137:00 am -
1 stop7h 14m
Deal found 8/17![JetBlue logo]()
$314
This Delta deal was found by Cheapflights users on 8/20. 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.
Tue 10/207:40 pm -
Nonstop2h 51m
Fri 10/237:25 am -
Nonstop2h 35m
Deal found 8/20![Delta logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/18. 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 11/143:59 pm -
1 stop8h 45m
Sun 11/152:35 pm -
1 stop8h 44m
Deal found 8/18![JetBlue logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/15. 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 9/16:42 pm -
Nonstop2h 58m
Wed 9/26:24 pm -
Nonstop2h 35m
Deal found 8/15![United Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 8/15. 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 11/138:40 pm -
Nonstop2h 56m
Sun 11/157:05 am -
Nonstop2h 27m
Deal found 8/15![Delta logo]()
$255
Last-minute flights from Boston to O'Hare IntlDiscover last-minute flight deals from Boston to O'Hare Intl. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to O'Hare Intl. Data last updated August 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:45 pm -
1 stop8h 14m
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:45 pm -
1 stop8h 14m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/15![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 8/17. 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.
Tue 9/112:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/17![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/18. 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 9/212:45 pm -
1 stop8h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 8/16. 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 9/212:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$183
This Trip.com deal was found by Cheapflights users on 8/17. 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 9/512:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/17![Frontier logo]()
$184
This Trip.com deal was found by Cheapflights users on 8/16. 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 9/1212:54 pm -
1 stop6h 29m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/16![Frontier logo]()
$187
One-way flights from Boston to O'Hare IntlSearch for one-way flight options from Boston to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
Search for one-way flight options from Boston to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:57 pm -
1 stop6h 34m
Deal found 8/20![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 8/19. 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 9/1111:36 am -
1 stop12h 23m
Deal found 8/19![Frontier logo]()
$104
This Faresmojo deal was found by Cheapflights users on 8/20. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 pm -
Nonstop2h 54m
Deal found 8/20![JetBlue logo]()
$105
This Travelocity deal was found by Cheapflights users on 8/16. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:11 am -
1 stop14h 39m
Deal found 8/16![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 8/20. 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 9/512:45 pm -
1 stop8h 23m
Deal found 8/20![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Deal found 8/19![Frontier logo]()
$110
This SmartFares deal was found by Cheapflights users on 8/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:40 pm -
Nonstop2h 51m
Deal found 8/20![Delta logo]()
$114
This Frontier deal was found by Cheapflights users on 8/16. 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 9/610:04 am -
1 stop14h 04m
Deal found 8/16![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:15 am -
1 stop10h 47m
Deal found 8/18![Frontier logo]()
$116
This Super.com deal was found by Cheapflights users on 8/17. 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 8/2612:45 pm -
1 stop8h 23m
Deal found 8/17![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/19. 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.
Mon 8/3112:45 pm -
1 stop8h 14m
Deal found 8/19![Frontier logo]()
$118
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 August 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Frontier) |
One-way from | $103 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $249 |
Good round-trip deal | $268 or less |
Good one-way deal | $175 or less |
Cheapflights Fare Finder
Customize 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 August 20, 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
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 10/1
4:30 pm-6:28 pm
Nonstop2h 58m
Chicago O'Hare Intl
Thu 10/8
7:25 am-11:00 am
Nonstop2h 35m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 10/8
8:30 pm-10:29 pm
Nonstop2h 59m
Chicago O'Hare Intl
Sun 10/11
9:24 pm-12:54 am
Nonstop2h 30m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 9/28
8:50 pm-10:32 pm
Nonstop2h 42m
Chicago O'Hare Intl
Fri 10/2
3:05 pm-6:52 pm
Nonstop2h 47m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 9/14
8:50 pm-10:32 pm
Nonstop2h 42m
Chicago O'Hare Intl
Fri 9/18
3:05 pm-6:52 pm
Nonstop2h 47m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 10/2
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Sun 10/4
7:35 am-11:08 am
Nonstop2h 33m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/20
7:40 pm-9:31 pm
Nonstop2h 51m
Chicago O'Hare Intl
Fri 10/23
7:25 am-11:00 am
Nonstop2h 35m
$255
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 11/13
8:40 pm-10:36 pm
Nonstop2h 56m
Chicago O'Hare Intl
Sun 11/15
7:05 am-10:32 am
Nonstop2h 27m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 9/20
7:00 am-8:48 am
Nonstop2h 48m
Chicago O'Hare Intl
Fri 9/25
8:24 pm-12:09 am
Nonstop2h 45m
$275
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 10/8
6:00 am-7:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Fri 10/9
9:24 pm-12:54 am
Nonstop2h 30m
$278
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 9/11
2:45 pm-11:08 pm
1 stop9h 23m
Chicago O'Hare Intl
Sun 9/13
7:00 am-3:14 pm
1 stop7h 14m
$314
Showing 1-10 of 24 resultsSorted by cheapest first
Compare providers for flights from Boston to O'Hare Intl
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 Boston to O'Hare Intl 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 Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Boston-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Chicago O'Hare Intl Airport 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 Boston-Chicago O'Hare Intl Airport 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 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 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 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?
To ensure you get the cheapest price possible for a flight from Boston to Chicago O'Hare Intl Airport, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 $196). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of $281). 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 August 20, 2026.
It’s optimal to fly from Boston to Chicago O'Hare Intl Airport in the evening. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Boston to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Boston to O'Hare Intl. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Boston to Chicago O'Hare Intl Airport flight should consider departing on Friday 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 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 171 minutes.
What is the most punctual flight time for Boston to Chicago flights?
Historically, flights departing in the morning 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 last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
The best insider tips for Boston to Chicago O'Hare Intl Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago O'Hare Intl Airport trip
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Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated August 20, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Boston to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Comfort
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
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.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Oakbrook Terrace
Delavan
South Holland
Libertyville
Gurnee
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
Racine
Great Lakes
Janesville
Joliet
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Top 4 airlines flying from Boston to O'Hare Intl
Discover the top 4 airlines that operate flights from Boston to O'Hare Intl. 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 7,457,451 searches. Data last updated August 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$195 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$263 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$279 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$267 | FlexibilityNo cancel fee | On-time71% |