$112+ Cheap flights from Boston (BOS) to O'Hare Intl (ORD)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Oct 12 — Oct 191
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 78 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 September 12, 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 September 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sat 10/2411:42 am -
1 stop7h 49m
Mon 10/267:44 pm -
1 stop13h 33m
Deal found 9/11![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sat 11/1411:27 am -
1 stop7h 49m
Mon 11/167:50 pm -
1 stop14h 40m
Deal found 9/11![Frontier logo]()
$227
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:52 pm -
1 stop6h 31m
Wed 9/303:50 pm -
1 stop17h 32m
Deal found 9/7![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 11/1012:15 pm -
1 stop7h 01m
Fri 11/137:50 pm -
1 stop13h 42m
Deal found 9/11![Frontier logo]()
$229
This deal was found by Cheapflights users on 9/11. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:15 am -
1 stop5h 43m
Mon 9/148:24 pm -
Nonstop2h 45m
Deal found 9/11![JetBlue logo]()
$230
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:52 pm -
1 stop6h 31m
Fri 10/23:50 pm -
1 stop17h 51m
Deal found 9/7![Frontier logo]()
$235
This Frontier deal was found by Cheapflights users on 9/9. 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 10/2112:57 pm -
1 stop6h 34m
Fri 10/238:11 pm -
1 stop13h 51m
Deal found 9/9![Frontier logo]()
$236
This JetBlue deal was found by Cheapflights users on 9/10. 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 10/34:11 pm -
1 stop6h 57m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/10![JetBlue logo]()
$240
This Super.com deal was found by Cheapflights users on 9/9. 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 10/76:55 am -
Nonstop2h 54m
Sun 10/119:38 am -
Nonstop2h 28m
Deal found 9/9![JetBlue logo]()
$241
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 September 12, 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 September 12, 2026.
This JetBlue deal was found by Cheapflights users on 9/10. 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 9/255:00 pm -
Nonstop3h 01m
Mon 9/287:00 am -
1 stop6h 27m
Deal found 9/10![JetBlue logo]()
$260
This United Airlines deal was found by Cheapflights users on 9/11. 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 9/256:00 am -
Nonstop2h 59m
Mon 9/286:24 pm -
Nonstop2h 35m
Deal found 9/11![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 9/9. 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 10/247:40 pm -
Nonstop2h 51m
Sat 10/3112:00 pm -
Nonstop2h 32m
Deal found 9/9![Delta logo]()
$275
This JetBlue deal was found by Cheapflights users on 9/11. 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 10/156:55 am -
Nonstop2h 52m
Tue 10/206:10 am -
1 stop7h 19m
Deal found 9/11![JetBlue logo]()
$272
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 11/261:35 pm -
Nonstop2h 55m
Tue 12/13:05 pm -
Nonstop2h 31m
Deal found 9/8![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 9/10. 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 1/82:48 pm -
1 stop5h 17m
Mon 1/112:20 pm -
Nonstop2h 29m
Deal found 9/10![United Airlines logo]()
$285
This JetBlue deal was found by Cheapflights users on 9/11. 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 9/265:15 am -
1 stop5h 43m
Sat 9/268:24 pm -
Nonstop2h 45m
Deal found 9/11![JetBlue logo]()
$282
This Delta deal was found by Cheapflights users on 9/11. 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 10/24:30 pm -
Nonstop2h 58m
Sun 10/47:35 am -
Nonstop2h 33m
Deal found 9/11![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/56:43 pm -
Nonstop2h 57m
Thu 10/89:24 pm -
Nonstop2h 30m
Deal found 9/9![United Airlines logo]()
$301
This JetBlue deal was found by Cheapflights users on 9/10. 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 12/172:46 pm -
Nonstop3h 02m
Mon 12/285:51 pm -
Nonstop2h 28m
Deal found 9/10![JetBlue logo]()
$305
This Delta deal was found by Cheapflights users on 9/8. 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 12/188:59 pm -
Nonstop3h 01m
Mon 12/216:40 pm -
Nonstop2h 47m
Deal found 9/8![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 9/10. 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 12/152:56 pm -
1 stop6h 53m
Sun 12/201:26 pm -
1 stop6h 26m
Deal found 9/10![Delta logo]()
$315
Last-minute flights from Boston to O'Hare IntlDiscover last-minute flight deals from Boston to O'Hare Intl. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to O'Hare Intl. Data last updated September 12, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:54 pm -
1 stop6h 29m
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 9/7![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sat 9/1912:54 pm -
1 stop6h 29m
Wed 9/303:50 pm -
1 stop17h 32m
Deal found 9/10![Frontier logo]()
$272
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
Nonstop2h 48m
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 9/7![Multiple Airlines logo]()
$269
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
Nonstop2h 48m
Fri 9/253:50 pm -
1 stop18h 01m
Deal found 9/7![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 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
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 9/8![Frontier logo]()
$259
This JetBlue deal was found by Cheapflights users on 9/10. 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.
Tue 9/225:15 am -
1 stop5h 43m
Sat 9/269:38 am -
Nonstop2h 28m
Deal found 9/10![JetBlue logo]()
$262
This Cheapflightsfares deal was found by Cheapflights users on 9/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:00 pm -
Nonstop3h 01m
Thu 10/18:24 pm -
Nonstop2h 45m
Deal found 9/7![JetBlue logo]()
$266
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Thu 10/18:24 pm -
Nonstop2h 45m
Deal found 9/7![Multiple Airlines logo]()
$267
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Sat 9/263:50 pm -
1 stop18h 08m
Deal found 9/7![Frontier logo]()
$270
This CheapOair deal was found by Cheapflights users on 9/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Sat 9/269:38 am -
Nonstop2h 28m
Deal found 9/7![Multiple Airlines logo]()
$277
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 September 12, 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 September 12, 2026.
This Frontier deal was found by Cheapflights users on 9/7. 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.
Tue 9/2912:52 pm -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 9/10. 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 11/1112:39 pm -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 9/7. 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.
Fri 10/212:54 pm -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$119
This Super.com deal was found by Cheapflights users on 9/10. 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 9/257:00 am -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$121
This Super.com deal was found by Cheapflights users on 9/11. 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.
Thu 10/111:17 am -
1 stop12h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 9/10. 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 10/2311:47 am -
1 stop21h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 9/10. 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.
Fri 12/119:35 am -
1 stop11h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$124
This JetBlue deal was found by Cheapflights users on 9/11. 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 9/265:15 am -
1 stop5h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![JetBlue logo]()
$125
This Frontier deal was found by Cheapflights users on 9/10. 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 11/1212:39 pm -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 9/7. 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 Super.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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$129
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 September 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $218 (Kiwi.com) |
One-way from | $112 (Frontier) |
Popular in | October |
Cheapest in | January |
Average price | $259 |
Good round-trip deal | $280 or less |
Good one-way deal | $162 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 September 12, 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
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 10/1
8:50 pm-10:32 pm
Nonstop2h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 10/1
10:36 am-12:29 pm
Nonstop2h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 12/8
5:00 pm-9:47 pm
1 stop5h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$143
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 10/25
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 3/9
8:10 pm-10:04 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/20
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 10/2
6:43 pm-8:40 pm
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 12/20
5:45 am-9:40 am
1 stop4h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/6
5:35 am-10:29 am
1 stop5h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 12/2
2:00 pm-8:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$162
Showing 1-10 of 23 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 September.
| 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 77 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 October is currently the most expensive (average of $284). 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 September 12, 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 26% 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 September 12, 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 at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Boston to Chicago flights?
Over the 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
Our travel experts
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 September 12, 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.
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
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
Lake Geneva
Naperville
Des Plaines
Glenview
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
South Holland
Elgin
Racine
Janesville
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
O'Hare Intl flight routes
Other flight options
Other flights from Boston
Popular flights
Alternative routes for Boston to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to O'Hare Intl by cabin class
Find flights from Boston to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 12, 2026.
Boston and O'Hare Intl flights
Browse other Boston and O'Hare Intl flight options. Last updated on September 12, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 September 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$199 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$95 | Average$268 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$131 | Average$282 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$141 | Average$270 | FlexibilityNo cancel fee | On-time71% |