$111+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Nov 6 — Nov 131
Round-trip
1 adult, Economy
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Find cheap flights from Boston to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in January or February, booked 15 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 October 7, 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 October 7, 2026.
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:27 am -
1 stop8h 09m
Mon 11/27:25 am -
Nonstop2h 35m
Deal found 10/5![Delta logo]()
$212
This CheapOair deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:39 pm -
1 stop7h 06m
Mon 11/98:15 pm -
Nonstop2h 44m
Deal found 10/5![Multiple Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:08 am -
1 stop14h 51m
Sat 12/55:46 pm -
Nonstop2h 28m
Deal found 10/6![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:39 pm -
1 stop6h 51m
Mon 11/96:00 am -
2 stops28h 30m
Deal found 10/6![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:39 pm -
1 stop6h 51m
Fri 11/61:00 pm -
Nonstop2h 49m
Deal found 10/6![Multiple Airlines logo]()
$219
This Priceline deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:15 pm -
1 stop7h 15m
Fri 11/131:00 pm -
Nonstop2h 49m
Deal found 10/5![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 15m
Mon 11/166:00 am -
2 stops28h 30m
Deal found 10/6![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:59 am -
Nonstop3h 01m
Sun 11/225:40 am -
1 stop27h 31m
Deal found 10/6![Multiple Airlines logo]()
$224
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:12 am -
1 stop8h 33m
Fri 10/308:24 pm -
Nonstop2h 44m
Deal found 10/6![Multiple Airlines logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:15 pm -
Nonstop3h 14m
Mon 11/21:00 pm -
Nonstop2h 48m
Deal found 10/6![JetBlue logo]()
$227
This JetBlue deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:59 am -
Nonstop3h 01m
Sat 11/141:00 pm -
Nonstop2h 49m
Deal found 10/6![JetBlue logo]()
$229
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 October 7, 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 October 7, 2026.
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/114:59 pm -
1 stop4h 16m
Tue 12/1511:35 am -
1 stop4h 52m
Deal found 10/6![Delta logo]()
$249
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:31 am -
Nonstop3h 03m
Sun 11/88:07 pm -
Nonstop2h 28m
Deal found 10/5![United Airlines logo]()
$258
This JetBlue deal was found by Cheapflights users on 10/2. 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 10/176:55 am -
1 stop5h 29m
Sat 11/71:00 pm -
Nonstop2h 49m
Deal found 10/2![JetBlue logo]()
$315
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:39 am -
1 stop5h 50m
Sun 11/86:20 am -
1 stop6h 50m
Deal found 10/6![Delta logo]()
$278
This United Airlines deal was found by Cheapflights users on 10/2. 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 10/256:00 am -
Nonstop3h 00m
Wed 10/289:20 pm -
Nonstop2h 26m
Deal found 10/2![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:30 am -
Nonstop3h 05m
Fri 11/276:00 am -
1 stop7h 38m
Deal found 10/5![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/269:12 am -
Nonstop3h 03m
Wed 10/288:01 pm -
Nonstop2h 28m
Deal found 10/3![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:40 pm -
1 stop7h 14m
Fri 11/277:05 am -
Nonstop2h 27m
Deal found 10/6![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/195:45 am -
Nonstop3h 06m
Sun 12/279:49 pm -
Nonstop2h 29m
Deal found 10/6![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:40 pm -
Nonstop2h 56m
Sun 11/157:05 am -
Nonstop2h 27m
Deal found 10/4![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/209:10 am -
Nonstop3h 06m
Sun 12/279:49 pm -
Nonstop2h 29m
Deal found 10/6![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/297:30 am -
Nonstop3h 03m
Thu 4/17:00 am -
1 stop5h 21m
Deal found 10/4![Delta logo]()
$325
Last-minute flights from Boston to O'Hare IntlDiscover last-minute flight deals from Boston to O'Hare Intl. Data last updated October 7, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to O'Hare Intl. Data last updated October 7, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:12 am -
1 stop8h 33m
Fri 10/308:24 pm -
Nonstop2h 44m
Deal found 10/6![Multiple Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:27 am -
1 stop8h 09m
Mon 11/27:25 am -
Nonstop2h 35m
Deal found 10/5![Delta logo]()
$212
This CheapOair deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:39 pm -
1 stop7h 06m
Mon 11/98:15 pm -
Nonstop2h 44m
Deal found 10/5![Multiple Airlines logo]()
$215
This Cheapflightsfares deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:15 pm -
Nonstop3h 14m
Mon 11/21:00 pm -
Nonstop2h 48m
Deal found 10/6![JetBlue logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:39 pm -
1 stop6h 51m
Mon 11/96:00 am -
2 stops28h 30m
Deal found 10/6![Frontier logo]()
$218
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:39 pm -
1 stop6h 51m
Fri 11/61:00 pm -
Nonstop2h 49m
Deal found 10/6![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:39 pm -
1 stop7h 15m
Mon 11/98:15 pm -
Nonstop2h 44m
Deal found 10/6![Multiple Airlines logo]()
$230
This Priceline deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:15 pm -
1 stop7h 15m
Fri 11/131:00 pm -
Nonstop2h 49m
Deal found 10/5![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 15m
Mon 11/166:00 am -
2 stops28h 30m
Deal found 10/6![Frontier logo]()
$223
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:35 pm -
Nonstop3h 09m
Wed 11/1810:35 am -
Nonstop2h 24m
Deal found 10/6![Delta logo]()
$229
This CheapOair deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:59 am -
Nonstop3h 01m
Sun 11/225:40 am -
1 stop27h 31m
Deal found 10/6![Multiple Airlines logo]()
$224
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 October 7, 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 October 7, 2026.
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:00 am -
1 stop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![United Airlines logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:08 am -
1 stop14h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$113
This KAYAK deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 pm -
Nonstop2h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:39 pm -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:57 pm -
1 stop6h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/212:39 pm -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:39 pm -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$127
This KAYAK deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:15 pm -
1 stop8h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$128
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:10 pm -
Nonstop2h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$129
This Expedia deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:06 am -
1 stop14h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$132
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 October 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $212 (Delta) |
One-way from | $111 (United Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $307 |
Good round-trip deal | $314 or less |
Good one-way deal | $175 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 7, 2026.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 11/19
9:05 am-2:49 pm
1 stop6h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$111
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 1/20
11:00 am-5:47 pm
1 stop7h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$111
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 12/29
5:45 am-9:40 am
1 stop4h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$156
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 10/17
6:55 am-11:24 am
1 stop5h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 11/20
8:25 pm-10:29 pm
Nonstop3h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 12/1
7:30 am-9:38 am
Nonstop3h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 4/3
8:15 am-10:12 am
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Wed 1/6
1:50 pm-3:50 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 4/1
4:10 pm-6:10 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 11/3
3:41 pm-10:18 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
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 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 Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | 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 14 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 $197). Flying from Boston to Chicago O'Hare Intl Airport in October is currently the most expensive (average of $307). 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 October 7, 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 22% 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 October 3, 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. Monday 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 172 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 Monday 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 9% 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 October 7, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andJetBlue 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
Entertainment
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Food
7.2
Crew
8.5
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
Naperville
Lake Geneva
Des Plaines
Glenview
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Aurora
Libertyville
Rockford
Hoffman Estates
Beloit
Orland Park
South Holland
Elgin
Racine
Janesville
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Top 4 airlines flying from Boston to O'Hare Intl
Discover the top 4 airlines that operate flights from Boston to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$73 | Average$210 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$100 | Average$272 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$289 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$274 | FlexibilityNo cancel fee | On-time71% |