$111+ Cheap flights from Chicago (CHI) 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Nov 18 — Nov 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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 to Boston Logan Intl are usually found in January or February, booked 50 days in advance, depart on a Saturday or Friday and return on a Friday
Cheap flight deals from Chicago to Boston
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Cheapest flights from Chicago to BostonExplore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:51 am -
1 stop6h 59m
Mon 11/164:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:55 am -
2 stops8h 05m
Tue 11/102:25 pm -
1 stop5h 40m
Deal found 10/15![Southwest logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 11/61:00 pm -
Nonstop2h 49m
Tue 11/109:59 am -
Nonstop3h 01m
Deal found 10/14![JetBlue logo]()
$227
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:10 am -
2 stops6h 40m
Mon 11/234:20 pm -
Nonstop2h 45m
Deal found 10/19![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/14. 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 11/137:05 am -
Nonstop2h 27m
Mon 11/164:35 pm -
Nonstop3h 09m
Deal found 10/14![Delta logo]()
$229
This CheapOair deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:35 am -
1 stop27h 36m
Sat 12/511:08 am -
1 stop15h 00m
Deal found 10/16![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop12h 29m
Tue 11/2411:06 am -
1 stop9h 41m
Deal found 10/15![Frontier logo]()
$230
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:05 am -
1 stop4h 55m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/14![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
1 stop6h 21m
Mon 11/236:00 pm -
1 stop5h 18m
Deal found 10/19![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:20 am -
1 stop5h 50m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/19![Southwest logo]()
$233
This deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:15 pm -
Nonstop2h 44m
Fri 11/65:05 pm -
Nonstop3h 12m
Deal found 10/15![JetBlue logo]()
$234
Best flights from Chicago to BostonDiscover carefully curated flight deals from Chicago to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
Discover carefully curated flight deals from Chicago to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
This Delta deal was found by Cheapflights users on 10/14. 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 12/143:05 pm -
Nonstop2h 31m
Wed 1/68:10 pm -
Nonstop2h 54m
Deal found 10/14![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:30 am -
Nonstop2h 30m
Sat 11/216:55 pm -
Nonstop2h 45m
Deal found 10/16![Southwest logo]()
$311
This JetBlue deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/187:55 pm -
Nonstop2h 26m
Sat 1/911:45 am -
Nonstop3h 04m
Deal found 10/17![JetBlue logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/317:55 am -
1 stop4h 31m
Sun 1/35:45 am -
Nonstop3h 06m
Deal found 10/18![United Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 10/14. 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 12/127:05 am -
Nonstop2h 31m
Mon 1/47:30 am -
Nonstop3h 03m
Deal found 10/14![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:10 pm -
1 stop4h 45m
Sun 11/85:10 am -
1 stop10h 00m
Deal found 10/14![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:05 am -
Nonstop2h 27m
Mon 11/232:00 pm -
1 stop5h 22m
Deal found 10/15![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/271:25 pm -
Nonstop2h 10m
Fri 1/295:40 am -
2 stops10h 05m
Deal found 10/14![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:15 am -
2 stops8h 05m
Mon 12/287:00 am -
Nonstop2h 45m
Deal found 10/15![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 10/14. 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 12/215:45 pm -
Nonstop2h 29m
Mon 12/285:30 am -
1 stop7h 23m
Deal found 10/14![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:25 am -
Nonstop2h 35m
Fri 11/134:35 pm -
Nonstop3h 09m
Deal found 10/17![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:25 pm -
Nonstop2h 20m
Thu 12/105:55 pm -
Nonstop2h 45m
Deal found 10/18![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:35 am -
Nonstop2h 24m
Sat 11/147:45 am -
Nonstop3h 10m
Deal found 10/16![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:30 am -
Nonstop2h 30m
Mon 12/712:50 pm -
Nonstop2h 50m
Deal found 10/17![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:19 am -
1 stop3h 56m
Sun 11/17:30 am -
Nonstop2h 54m
Deal found 10/15![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:40 pm -
Nonstop2h 15m
Mon 12/75:20 am -
1 stop7h 45m
Deal found 10/16![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2512:38 pm -
1 stop5h 12m
Thu 11/265:20 pm -
1 stop7h 00m
Deal found 10/15![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:30 am -
1 stop6h 14m
Mon 11/26:25 pm -
1 stop6h 32m
Deal found 10/18![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:04 am -
1 stop6h 40m
Sun 11/15:39 am -
1 stop4h 53m
Deal found 10/15![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:29 pm -
1 stop5h 15m
Mon 11/165:40 pm -
1 stop6h 14m
Deal found 10/17![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:12 am -
1 stop5h 58m
Sun 11/85:30 am -
1 stop5h 33m
Deal found 10/15![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:29 pm -
1 stop5h 15m
Sat 11/285:30 am -
1 stop5h 16m
Deal found 10/17![Delta logo]()
$355
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:12 am -
1 stop5h 59m
Mon 11/95:30 am -
1 stop5h 16m
Deal found 10/18![Delta logo]()
$355
Last-minute flights from Chicago to BostonDiscover last-minute flight deals from Chicago to Boston. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Boston. Data last updated October 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:05 am -
1 stop4h 55m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/14![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:55 am -
2 stops8h 05m
Tue 11/102:25 pm -
1 stop5h 40m
Deal found 10/15![Southwest logo]()
$226
This deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:15 pm -
Nonstop2h 44m
Fri 11/65:05 pm -
Nonstop3h 12m
Deal found 10/15![JetBlue logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 11/61:00 pm -
Nonstop2h 49m
Tue 11/109:59 am -
Nonstop3h 01m
Deal found 10/14![JetBlue logo]()
$227
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:51 am -
1 stop6h 59m
Mon 11/164:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:20 am -
1 stop5h 50m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/19![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 10/14. 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 11/133:05 pm -
Nonstop2h 24m
Sat 11/147:55 pm -
Nonstop2h 56m
Deal found 10/14![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:10 am -
2 stops6h 40m
Mon 11/234:20 pm -
Nonstop2h 45m
Deal found 10/19![Southwest logo]()
$228
This Frontier deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop12h 29m
Tue 11/2411:06 am -
1 stop9h 41m
Deal found 10/15![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop12h 29m
Thu 12/311:08 am -
1 stop28h 33m
Deal found 10/19![Frontier logo]()
$235
This Cheapflightsfares deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:12 pm -
1 stop15h 59m
Fri 11/2711:06 am -
1 stop14h 37m
Deal found 10/15![Frontier logo]()
$236
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
One-way flights from Chicago to BostonSearch for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/14. 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 11/166:05 pm -
1 stop4h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:00 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Southwest logo]()
$111
This Super.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:40 am -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$114
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:50 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$117
This KAYAK deal was found by Cheapflights users on 10/14. 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 11/163:05 pm -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$118
This Trip.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 11/197:50 pm -
1 stop10h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 11/196:42 pm -
1 stop11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 10/14![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:37 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$123
Find flight deals from Chicago to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Delta) |
One-way from | $111 (United Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $296 |
Good round-trip deal | $295 or less |
Good one-way deal | $174 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 19, 2026.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/7
9:40 am-4:50 pm
1 stop6h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 12/5
10:20 am-7:25 pm
2 stops8h 05m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$116
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 1/26
3:25 pm-8:50 pm
1 stop4h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 11/16
3:05 pm-6:29 pm
Nonstop2h 24m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 12/3
1:20 pm-9:55 pm
2 stops7h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 2/24
8:15 am-4:05 pm
2 stops6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 11/23
1:59 pm-5:24 pm
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 11/22
7:50 am-11:10 am
Nonstop2h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/29
11:00 am-2:25 pm
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/21
7:45 am-11:00 am
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
Showing 1-10 of 46 resultsSorted by cheapest first
Compare providers for flights from Chicago 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 Chicago 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 |
- Most accurate provider: When it comes to deals on Chicago-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.
CHI-BOS
MDW-BOS
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 to Boston
CHI-BOS
MDW-BOS
ORD-BOS
What is the cheapest month to book a flight from Chicago to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $201). Flying from Chicago to Boston in October is currently the most expensive (average of $319). 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 CHI to BOS?
Find hourly flight availability from Chicago 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 19, 2026.
It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 15% on the flight price compared to flying in the afternoon, which is usually more expensive.
Weekly flight availability from Chicago to Boston
Explore weekly flight availability from Chicago to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 19, 2026.
The most flights from CHI to BOS are scheduled on a Sunday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (59 on average).
How much does it cost to fly round-trip from Chicago to Boston?
Airfare is below average for this route at the moment.
Chicago to Boston flights typically cost between $227 and $394 in November.The cheapest round-trip price found within the last 5 days was $223 on Delta (Nov 12-Nov 16).
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 155 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 Monday 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.
How far ahead should I book a flight from Chicago to Boston?
The price you pay for your flight from Chicago to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Boston?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Boston. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Tuesday at noon 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.
The best insider tips for Chicago 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 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 19, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Boston have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Related info for your journey
Find useful and relevant information for your journey from Chicago 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
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
Browse thousands of different options on Cheapflights for your next trip
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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.
Complete your trip
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Search flights from Chicago to Boston by cabin class
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Chicago and Boston flights
Browse other Chicago and Boston flight options. Last updated on October 19, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Chicago to Boston
Discover the top 5 airlines that operate flights from Chicago 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$316 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$271 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$334 | FlexibilityNo cancel fee | On-time63% |