$110+ Cheap flights from O'Hare Intl (ORD) to Boston (BOS)
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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 11 — Nov 181
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 February, booked 61 days in advance, depart on a Saturday or Friday 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 October 12, 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 October 12, 2026.
This CheapOair deal was found by Cheapflights users on 10/12. 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 11/101:00 pm -
Nonstop2h 49m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/12![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:15 pm -
Nonstop2h 44m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/8![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 10/8. 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 10/296:30 am -
1 stop7h 24m
Mon 11/26:25 pm -
1 stop6h 32m
Deal found 10/8![Delta logo]()
$221
This CheapOair deal was found by Cheapflights users on 10/7. 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.
Wed 10/218:46 am -
1 stop25h 16m
Sat 10/2411:42 am -
1 stop7h 49m
Deal found 10/7![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 10/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:00 pm -
Nonstop2h 49m
Mon 11/1612:39 pm -
1 stop7h 06m
Deal found 10/9![Multiple Airlines logo]()
$224
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:10 am -
1 stop7h 19m
Tue 10/275:15 pm -
Nonstop3h 14m
Deal found 10/7![JetBlue logo]()
$225
This Traveloka deal was found by Cheapflights users on 10/8. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:00 pm -
Nonstop2h 49m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 10/8![JetBlue logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:15 pm -
Nonstop2h 44m
Tue 11/179:59 am -
Nonstop3h 01m
Deal found 10/8![JetBlue logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:05 am -
1 stop28h 57m
Mon 1/1110:24 am -
1 stop15h 31m
Deal found 10/8![Frontier logo]()
$228
This Delta deal was found by Cheapflights users on 10/8. 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 11/137:45 pm -
Nonstop2h 23m
Tue 11/178:40 pm -
Nonstop2h 56m
Deal found 10/8![Delta logo]()
$229
This Priceline deal was found by Cheapflights users on 10/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:00 pm -
Nonstop2h 48m
Fri 11/1312:39 pm -
1 stop7h 06m
Deal found 10/8![Multiple Airlines logo]()
$230
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 October 12, 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 October 12, 2026.
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:55 pm -
1 stop4h 57m
Sat 10/311:05 pm -
1 stop4h 21m
Deal found 10/7![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Fri 10/306:00 pm -
Nonstop2h 30m
Mon 11/28:25 pm -
Nonstop3h 04m
Deal found 10/8![United Airlines logo]()
$229
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:38 pm -
1 stop7h 11m
Sat 10/246:55 am -
Nonstop2h 52m
Deal found 10/7![JetBlue logo]()
$312
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Thu 10/296:59 am -
1 stop4h 27m
Fri 10/306:00 am -
Nonstop3h 00m
Deal found 10/7![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:35 am -
Nonstop2h 24m
Sat 1/95:30 am -
1 stop4h 28m
Deal found 10/7![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 12/37:45 pm -
Nonstop2h 32m
Fri 12/118:59 pm -
Nonstop2h 58m
Deal found 10/11![Delta logo]()
$285
This United Airlines deal was found by Cheapflights users on 10/7. 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 12/196:50 am -
Nonstop2h 27m
Sat 1/25:45 am -
Nonstop3h 06m
Deal found 10/7![United Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Tue 12/224:00 pm -
Nonstop2h 29m
Sun 1/37:40 pm -
1 stop5h 19m
Deal found 10/9![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 10/10. 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.
Sat 11/73:40 pm -
1 stop8h 40m
Sun 11/87:30 am -
Nonstop2h 54m
Deal found 10/10![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 10/293:05 pm -
Nonstop2h 39m
Fri 10/304:15 pm -
1 stop8h 42m
Deal found 10/11![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 10/9. 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.
Sun 11/157:05 am -
Nonstop2h 27m
Fri 11/206:05 am -
1 stop7h 41m
Deal found 10/9![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 10/11. 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.
Sun 12/207:05 am -
Nonstop2h 28m
Mon 1/412:00 pm -
1 stop6h 47m
Deal found 10/11![Delta logo]()
$325
Last-minute flights from O'Hare Intl to BostonDiscover last-minute flight deals from O'Hare Intl to Boston. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Boston. Data last updated October 12, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/7. 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.
Wed 10/218:46 am -
1 stop25h 16m
Sat 10/2411:42 am -
1 stop7h 49m
Deal found 10/7![Frontier logo]()
$222
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:10 am -
1 stop7h 19m
Tue 10/275:15 pm -
Nonstop3h 14m
Deal found 10/7![JetBlue logo]()
$225
This Delta deal was found by Cheapflights users on 10/8. 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 10/296:30 am -
1 stop7h 24m
Mon 11/26:25 pm -
1 stop6h 32m
Deal found 10/8![Delta logo]()
$221
This Priceline deal was found by Cheapflights users on 10/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:00 pm -
Nonstop2h 48m
Fri 11/1312:39 pm -
1 stop7h 06m
Deal found 10/8![Multiple Airlines logo]()
$230
This Priceline deal was found by Cheapflights users on 10/12. 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.
Thu 11/51:00 pm -
Nonstop2h 48m
Mon 11/912:39 pm -
1 stop7h 06m
Deal found 10/12![Multiple Airlines logo]()
$232
This CheapOair deal was found by Cheapflights users on 10/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:00 pm -
Nonstop2h 49m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/10![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/111:00 pm -
Nonstop2h 49m
Mon 11/1612:39 pm -
1 stop7h 06m
Deal found 10/9![Multiple Airlines logo]()
$224
This Traveloka deal was found by Cheapflights users on 10/8. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:00 pm -
Nonstop2h 49m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 10/8![JetBlue logo]()
$226
This CheapOair deal was found by Cheapflights users on 10/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:15 pm -
Nonstop2h 44m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/8![Multiple Airlines logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:15 pm -
Nonstop2h 44m
Tue 11/179:59 am -
Nonstop3h 01m
Deal found 10/8![JetBlue logo]()
$227
This Delta deal was found by Cheapflights users on 10/8. 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 11/137:45 pm -
Nonstop2h 23m
Tue 11/178:40 pm -
Nonstop2h 56m
Deal found 10/8![Delta logo]()
$229
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 October 12, 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 October 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Wed 12/25:35 am -
1 stop27h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$110
This United Airlines deal was found by Cheapflights users on 10/8. 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 11/55:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![United Airlines logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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.
Fri 12/45:24 pm -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 10/8. 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.
Fri 12/1110:37 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/610:37 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$122
This JetBlue deal was found by Cheapflights users on 10/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:10 am -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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.
Fri 11/68:15 pm -
Nonstop2h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$127
This Delta deal was found by Cheapflights users on 10/8. 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 12/117:45 pm -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:55 am -
1 stop24h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$131
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 October 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (CheapOair) |
One-way from | $110 (Kiwi.com) |
Popular in | September |
Cheapest in | January |
Average price | $326 |
Good round-trip deal | $294 or less |
Good one-way deal | $171 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 7,457,451 searches. Data last updated October 12, 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
Fri 10/30
6:07 pm-11:59 pm
1 stop4h 52m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
Quickest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 1/8
2:55 pm-6:17 pm
Nonstop2h 22m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 11/26
7:05 am-10:32 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 2/12
10:25 am-2:02 pm
Nonstop2h 37m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/22
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 11/15
7:05 am-10:32 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/24
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 11/8
10:30 am-1:59 pm
Nonstop2h 29m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 11/9
7:05 am-10:32 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 12/12
5:33 pm-11:47 pm
1 stop5h 14m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$167
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 October.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 60 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 $206). Flying from Chicago O'Hare Intl Airport to Boston in September is currently the most expensive (average of $334). 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 October 12, 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 21% 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 October 10, 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 afternoons 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 26% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 159 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 22% of flights being delayed.
The best insider tips for Chicago O'Hare Intl Airport to Boston 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 Chicago O'Hare Intl Airport to Boston trip
Our travel experts
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 October 12, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andJetBlue 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
Overall
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Entertainment
7.8
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
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Londonderry
York Beach
Revere
Fitchburg
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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O'Hare Intl and Boston flights
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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 7,457,451 searches. Data last updated October 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$251 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$313 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$142 | Average$270 | FlexibilityNo cancel fee | On-time71% |