$107+ Cheap flights from O'Hare Intl (ORD) to Boston (BOS)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 2 — Oct 91
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 November, booked 61 days in advance, depart on a Saturday or Thursday and return on a Friday
Cheap flight deals from O'Hare Intl to Boston
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to BostonExplore the most affordable flight options available from O'Hare Intl to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 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 September 2, 2026.
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Sat 9/193:50 pm -
1 stop18h 08m
Wed 9/237:00 am -
Nonstop2h 48m
Deal found 8/27![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Sat 9/269:38 am -
Nonstop2h 28m
Fri 10/212:54 pm -
1 stop6h 29m
Deal found 8/27![Multiple Airlines logo]()
$206
This CheapOair deal was found by Cheapflights users on 8/28. 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.
Sat 9/193:50 pm -
1 stop18h 08m
Mon 9/2112:54 pm -
1 stop6h 29m
Deal found 8/28![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 9/1. 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 10/98:11 pm -
1 stop13h 51m
Mon 10/126:55 am -
Nonstop2h 52m
Deal found 9/1![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 8/27. 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Mon 10/269:59 am -
Nonstop3h 00m
Deal found 8/27![JetBlue logo]()
$215
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:00 am -
Nonstop2h 39m
Tue 9/295:45 pm -
Nonstop3h 20m
Deal found 9/1![American Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 9/1. 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 10/110:30 am -
Nonstop2h 35m
Mon 10/58:50 pm -
Nonstop2h 42m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. 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 10/18:24 pm -
Nonstop2h 45m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/1![JetBlue logo]()
$218
This Frontier deal was found by Cheapflights users on 9/1. 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 10/238:11 pm -
1 stop13h 51m
Tue 10/2711:12 am -
1 stop8h 33m
Deal found 9/1![Frontier logo]()
$221
This CheapOair deal was found by Cheapflights users on 9/1. 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 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/1![Frontier logo]()
$222
This Super.com deal was found by Cheapflights users on 9/1. 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 10/28:24 pm -
Nonstop2h 45m
Mon 10/56:50 am -
Nonstop2h 52m
Deal found 9/1![JetBlue logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 9/1. 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 10/98:00 pm -
Nonstop2h 58m
Thu 10/155:12 pm -
Nonstop3h 02m
Deal found 9/1![JetBlue logo]()
$224
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 September 2, 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 September 2, 2026.
This Delta deal was found by Cheapflights users on 9/1. 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 10/157:25 am -
Nonstop2h 35m
Tue 10/204:25 pm -
Nonstop2h 55m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. 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 11/108:15 pm -
Nonstop2h 44m
Wed 11/185:05 pm -
Nonstop3h 12m
Deal found 9/1![JetBlue logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Sun 9/277:30 am -
Nonstop2h 31m
Wed 9/309:23 am -
Nonstop2h 52m
Deal found 8/28![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 9/1. 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 9/264:35 pm -
Nonstop2h 45m
Tue 9/297:30 am -
Nonstop2h 54m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:15 pm -
Nonstop2h 30m
Tue 11/1711:15 am -
Nonstop3h 05m
Deal found 8/28![JetBlue logo]()
$275
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:24 pm -
Nonstop2h 30m
Sun 9/276:00 am -
Nonstop2h 59m
Deal found 8/29![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 8/28. 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 10/63:05 pm -
Nonstop2h 39m
Sun 10/117:30 am -
Nonstop2h 54m
Deal found 8/28![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 8/29. 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 10/47:35 am -
Nonstop2h 33m
Sat 10/107:40 pm -
Nonstop2h 51m
Deal found 8/29![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 8/30. 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 10/87:25 am -
Nonstop2h 35m
Sun 10/117:30 am -
Nonstop2h 54m
Deal found 8/30![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 8/31. 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 9/225:40 pm -
1 stop4h 37m
Tue 9/299:10 am -
1 stop4h 49m
Deal found 8/31![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 9/1. 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 9/252:29 pm -
1 stop6h 57m
Sun 9/277:00 am -
1 stop6h 59m
Deal found 9/1![Delta logo]()
$335
This KAYAK deal was found by Cheapflights users on 9/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:30 am -
Nonstop2h 35m
Wed 9/164:30 pm -
Nonstop2h 58m
Deal found 9/1![Delta logo]()
$335
Last-minute flights from O'Hare Intl to BostonDiscover last-minute flight deals from O'Hare Intl to Boston. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Boston. Data last updated September 2, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Sat 9/193:50 pm -
1 stop18h 08m
Wed 9/237:00 am -
Nonstop2h 48m
Deal found 8/27![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 8/28. 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.
Sat 9/193:50 pm -
1 stop18h 08m
Mon 9/2112:54 pm -
1 stop6h 29m
Deal found 8/28![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 9/1. 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 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/1![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 8/27. 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.
Sat 9/269:38 am -
Nonstop2h 28m
Fri 10/212:54 pm -
1 stop6h 29m
Deal found 8/27![Multiple Airlines logo]()
$206
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:00 am -
Nonstop2h 39m
Tue 9/295:45 pm -
Nonstop3h 20m
Deal found 9/1![American Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 9/1. 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 10/110:30 am -
Nonstop2h 35m
Mon 10/58:50 pm -
Nonstop2h 42m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. 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 10/18:24 pm -
Nonstop2h 45m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/1![JetBlue logo]()
$218
This Super.com deal was found by Cheapflights users on 9/1. 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 10/28:24 pm -
Nonstop2h 45m
Tue 10/66:55 am -
Nonstop2h 54m
Deal found 9/1![JetBlue logo]()
$223
This CheapOair deal was found by Cheapflights users on 9/1. 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 10/98:11 pm -
1 stop13h 51m
Mon 10/126:55 am -
Nonstop2h 52m
Deal found 9/1![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 9/1. 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 10/98:00 pm -
Nonstop2h 58m
Thu 10/155:12 pm -
Nonstop3h 02m
Deal found 9/1![JetBlue logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 8/27. 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Mon 10/269:59 am -
Nonstop3h 00m
Deal found 8/27![JetBlue logo]()
$215
This Frontier deal was found by Cheapflights users on 9/1. 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 10/238:11 pm -
1 stop13h 51m
Tue 10/2711:12 am -
1 stop8h 33m
Deal found 9/1![Frontier logo]()
$221
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 September 2, 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 September 2, 2026.
This Super.com deal was found by Cheapflights users on 8/27. 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 9/287:00 am -
1 stop6h 27m
Deal found 8/27![JetBlue logo]()
$107
This American Airlines deal was found by Cheapflights users on 9/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:19 pm -
Nonstop2h 35m
Deal found 9/1![American Airlines logo]()
$108
This Delta deal was found by Cheapflights users on 8/28. 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 9/287:30 pm -
Nonstop2h 39m
Deal found 8/28![Delta logo]()
$109
This Jetabroad deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:38 pm -
1 stop7h 11m
Deal found 8/28![JetBlue logo]()
$111
This Super.com deal was found by Cheapflights users on 9/1. 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 9/258:24 pm -
Nonstop2h 45m
Deal found 9/1![JetBlue logo]()
$114
This Super.com deal was found by Cheapflights users on 8/28. 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 9/163:50 pm -
1 stop17h 32m
Deal found 8/28![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 8/28. 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 9/303:50 pm -
1 stop17h 32m
Deal found 8/28![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 9/1. 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 pm -
Nonstop2h 39m
Deal found 9/1![Delta logo]()
$118
This Trip.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 8/28![Frontier logo]()
$119
This Trip.com deal was found by Cheapflights users on 8/28. 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.
Fri 9/1811:15 am -
1 stop22h 36m
Deal found 8/28![Frontier logo]()
$120
This Super.com deal was found by Cheapflights users on 8/31. 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 10/238:11 pm -
1 stop13h 51m
Deal found 8/31![Frontier logo]()
$121
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 September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $211 (CheapOair) |
One-way from | $107 (Super.com) |
Popular in | August |
Cheapest in | January |
Average price | $258 |
Good round-trip deal | $255 or less |
Good one-way deal | $158 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 September 2, 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
Thu 10/15
7:25 am-11:00 am
Nonstop2h 35m
Boston Logan Intl
Tue 10/20
4:25 pm-6:20 pm
Nonstop2h 55m
$217
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 11/10
8:15 pm-11:59 pm
Nonstop2h 44m
Boston Logan Intl
Wed 11/18
5:05 pm-7:17 pm
Nonstop3h 12m
$217
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 9/26
4:35 pm-8:20 pm
Nonstop2h 45m
Boston Logan Intl
Tue 9/29
7:30 am-9:24 am
Nonstop2h 54m
$217
Quickest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 9/27
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Wed 9/30
9:23 am-11:15 am
Nonstop2h 52m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 11/9
2:15 pm-5:45 pm
Nonstop2h 30m
Boston Logan Intl
Tue 11/17
11:15 am-1:20 pm
Nonstop3h 05m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/25
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Sun 9/27
6:00 am-7:59 am
Nonstop2h 59m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/6
3:05 pm-6:44 pm
Nonstop2h 39m
Boston Logan Intl
Sun 10/11
7:30 am-9:24 am
Nonstop2h 54m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 10/4
7:35 am-11:08 am
Nonstop2h 33m
Boston Logan Intl
Sat 10/10
7:40 pm-9:31 pm
Nonstop2h 51m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/8
7:25 am-11:00 am
Nonstop2h 35m
Boston Logan Intl
Sun 10/11
7:30 am-9:24 am
Nonstop2h 54m
$295
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 9/22
5:40 pm-11:17 pm
1 stop4h 37m
Boston Logan Intl
Tue 9/29
9:10 am-12:59 pm
1 stop4h 49m
$315
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 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 Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | 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 $205). Flying from Chicago O'Hare Intl Airport to Boston in August is currently the most expensive (average of $298). 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 September 2, 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 24% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Boston?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Boston. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
How often are flights from Chicago to Boston delayed?
About 25% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 154 minutes.
What is the most punctual flight time for Chicago to Boston flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Boston flights?
Over the last year, Delta have had the lowest number of delays on this route, with just 20% 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 September 2, 2026.
Peruse reviews from past customers who have flown with Delta,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Boston to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
6.0
GoodColin,Sep 2024
LHR - BOS
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
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
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York Beach
Londonderry
Revere
Fitchburg
North Falmouth
Swansea
Braintree
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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 September 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$187 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$245 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$291 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$257 | FlexibilityNo cancel fee | On-time71% |