$111+ Cheap flights from Chicago (CHI) to Massachusetts
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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Massachusetts 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
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Cheapest flights from Chicago to MassachusettsExplore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 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.
Sat 11/216:15 pm -
1 stop5h 53m
Mon 11/304:35 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 Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am -
2 stops28h 30m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/19![Frontier logo]()
$224
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 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 American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:16 pm -
Nonstop2h 33m
Sat 11/74:41 pm -
Nonstop3h 14m
Deal found 10/15![American Airlines 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.
Sat 11/149:59 am -
1 stop7h 28m
Mon 11/166:00 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 MassachusettsDiscover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 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.
Wed 11/257:05 am -
Nonstop2h 27m
Mon 11/3012:00 pm -
1 stop7h 22m
Deal found 10/19![Delta logo]()
$223
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:29 am -
1 stop9h 38m
Sun 11/155:36 pm -
1 stop6h 54m
Deal found 10/14![American Airlines logo]()
$286
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:15 am -
Nonstop2h 19m
Wed 11/258:25 pm -
Nonstop3h 04m
Deal found 10/17![United Airlines logo]()
$311
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 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.
Sat 11/145:05 pm -
1 stop5h 49m
Tue 11/174:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
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.
Fri 11/612:00 pm -
Nonstop2h 32m
Wed 11/187:30 am -
Nonstop3h 05m
Deal found 10/19![Delta logo]()
$274
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 United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:50 am -
Nonstop2h 27m
Sun 1/35:45 am -
Nonstop3h 06m
Deal found 10/16![United Airlines logo]()
$327
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:29 am -
1 stop9h 52m
Sun 11/225:46 pm -
1 stop14h 39m
Deal found 10/17![American Airlines logo]()
$331
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.
Thu 11/1910:35 am -
Nonstop2h 24m
Sun 11/228:40 pm -
Nonstop2h 56m
Deal found 10/17![Delta logo]()
$287
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 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 11/214:40 pm -
Nonstop2h 23m
Mon 11/238:40 pm -
Nonstop2h 56m
Deal found 10/15![Delta logo]()
$287
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 10/17. 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.
Tue 11/310:05 am -
1 stop4h 22m
Wed 11/44:10 pm -
1 stop7h 07m
Deal found 10/17![Delta logo]()
$300
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:22 am -
1 stop9h 16m
Mon 12/77:04 pm -
2 stops14h 55m
Deal found 10/17![American Airlines logo]()
$403
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 Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:00 pm -
1 stop5h 45m
Wed 11/47:00 am -
1 stop6h 00m
Deal found 10/16![Multiple Airlines logo]()
$922
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.
Mon 11/210:05 am -
1 stop4h 22m
Fri 11/64:10 pm -
1 stop7h 07m
Deal found 10/18![Delta logo]()
$300
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 American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:39 am -
1 stop7h 42m
Mon 11/235:46 pm -
1 stop14h 39m
Deal found 10/19![American Airlines logo]()
$406
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 11/45:27 am -
2 stops9h 00m
Mon 11/94:00 pm -
1 stop5h 45m
Deal found 10/15![Delta logo]()
$310
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 10/16. 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 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 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.
Fri 11/277:05 am -
Nonstop2h 27m
Wed 12/27:30 am -
Nonstop3h 08m
Deal found 10/16![Delta 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.
Fri 10/306:04 am -
1 stop6h 40m
Sun 11/15:39 am -
1 stop4h 53m
Deal found 10/15![Delta logo]()
$355
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/11:00 pm -
1 stop5h 45m
Thu 11/59:20 am -
1 stop10h 57m
Deal found 10/17![Multiple Airlines logo]()
$963
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 Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:00 pm -
1 stop5h 45m
Sat 11/77:00 am -
1 stop6h 00m
Deal found 10/18![Multiple Airlines logo]()
$972
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
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated October 20, 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 American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:16 pm -
Nonstop2h 33m
Sat 11/74:41 pm -
Nonstop3h 14m
Deal found 10/15![American Airlines logo]()
$229
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am -
2 stops28h 30m
Thu 11/1912:39 pm -
1 stop7h 06m
Deal found 10/19![Frontier logo]()
$224
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 10/19. 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.
Sat 11/145:42 pm -
1 stop5h 02m
Tue 11/177:00 pm -
1 stop5h 54m
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.
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 10/19. 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.
Sat 11/216:15 pm -
1 stop5h 53m
Mon 11/304:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
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 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 MassachusettsSearch for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
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.
Wed 11/43:50 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![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 Frontier 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 Frontier 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 10/18![Frontier logo]()
$116
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.
Wed 11/255:05 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$117
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 11/188:00 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$117
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:35 pm -
1 stop11h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$123
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:00 am -
2 stops22h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$124
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$124
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.
Sat 12/199:21 pm -
1 stop10h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$126
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:16 pm -
1 stop16h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Allegiant Air logo]()
$126
Find flight deals from Chicago to Massachusetts
Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Delta) |
One-way from | $111 (Southwest) |
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 Massachusetts 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 20, 2026.
Use the filters below to find and compare flights from Chicago to Massachusetts 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
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 11/19
7:00 am-12:25 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
Sat 11/14
1:30 pm-6:57 pm
1 stop4h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
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
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
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
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Wed 11/4
10:05 am-3:27 pm
1 stop4h 22m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Sun 11/1
7:30 am-3:27 pm
1 stop6h 57m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chicago with our price prediction graph.
ORD-BOS
MDW-BOS
ORD-ORH
ORD-ACK
ORD-PVC
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 Massachusetts
CHI-USMA
ORD-BOS
MDW-BOS
ORD-ORH
ORD-ACK
What is the cheapest month to book a flight from Chicago to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $201). Flying from Chicago to Massachusetts 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 MA?
Find hourly flight availability from Chicago to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2026.
One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 41% on airfare.
Weekly flight availability from Chicago to Massachusetts
Explore weekly flight availability from Chicago to Massachusetts. 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 20, 2026.
The most flights from CHI to USMA 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 Massachusetts?
Airfare is typical for this route at the moment.
Chicago to Massachusetts flights typically cost between $210 and $383 in November.The cheapest round-trip price found within the last 5 days was $223 on Delta (Nov 21-Dec 5).
How far ahead should I book a flight from Chicago to Massachusetts?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Massachusetts. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Massachusetts. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Chicago to Massachusetts 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.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated October 20, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
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 Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Massachusetts by cabin class
Find flights from Chicago to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Massachusetts flights
Browse other Chicago and Massachusetts flight options. Last updated on October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Massachusetts flights
Consider these flights traveling from Chicago to Massachusetts.
Top 5 airlines flying from Chicago to Massachusetts
Discover the top 5 airlines that operate flights from Chicago to Massachusetts. 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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$358 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$318 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$316 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$334 | FlexibilityNo cancel fee | On-time63% |