$111+ Cheap flights from Massachusetts to Chicago (CHI)
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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Chicago 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Chicago
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Cheapest flights from Massachusetts to ChicagoExplore the most affordable flight options available from Massachusetts to Chicago. 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 Massachusetts to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop8h 03m
Wed 11/181:00 pm -
Nonstop2h 49m
Deal found 10/19![Multiple Airlines logo]()
$212
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 12/312:50 pm -
Nonstop2h 50m
Thu 12/101:15 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$213
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 11/128:40 pm -
Nonstop2h 56m
Mon 11/167:45 pm -
Nonstop2h 23m
Deal found 10/19![Delta logo]()
$213
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 12/35:55 pm -
Nonstop2h 45m
Mon 12/78:30 am -
Nonstop2h 30m
Deal found 10/19![Southwest logo]()
$214
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 11/128:16 am -
Nonstop3h 14m
Mon 11/163:16 pm -
Nonstop2h 33m
Deal found 10/19![American Airlines logo]()
$214
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.
Thu 11/1912:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$215
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.
Wed 11/1812:39 pm -
1 stop12h 08m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$218
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 11/1712:15 pm -
1 stop7h 15m
Wed 12/21:19 pm -
1 stop19h 52m
Deal found 10/19![Frontier logo]()
$218
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:42 pm -
1 stop6h 51m
Tue 12/82:25 pm -
Nonstop2h 30m
Deal found 10/19![United Airlines logo]()
$219
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop7h 20m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 10/16![Frontier logo]()
$220
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:34 am -
1 stop11h 26m
Sat 12/197:55 pm -
Nonstop2h 26m
Deal found 10/19![Multiple Airlines logo]()
$222
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:39 pm -
1 stop6h 51m
Fri 11/131:00 pm -
Nonstop2h 49m
Deal found 10/19![Multiple Airlines logo]()
$224
Best flights from Massachusetts to ChicagoDiscover carefully curated flight deals from Massachusetts to Chicago 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 Massachusetts to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
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 12/2910:25 pm -
Nonstop3h 00m
Mon 1/43:35 pm -
Nonstop2h 15m
Deal found 10/19![Southwest logo]()
$214
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 11/217:45 am -
Nonstop3h 10m
Wed 12/22:39 pm -
1 stop6h 41m
Deal found 10/19![Delta logo]()
$223
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 12/251:53 pm -
1 stop5h 37m
Wed 12/306:45 am -
1 stop10h 53m
Deal found 10/15![American Airlines logo]()
$300
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.
Sun 11/16:00 am -
Nonstop3h 00m
Wed 11/48:12 pm -
Nonstop2h 28m
Deal found 10/16![United Airlines logo]()
$335
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.
Fri 1/87:10 am -
Nonstop3h 00m
Mon 1/119:00 am -
Nonstop2h 15m
Deal found 10/19![Southwest logo]()
$237
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 1/15:30 am -
1 stop5h 19m
Mon 1/42:30 pm -
1 stop4h 54m
Deal found 10/19![Delta logo]()
$263
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 12/114:08 pm -
1 stop5h 37m
Tue 12/158:50 am -
1 stop5h 17m
Deal found 10/17![Delta logo]()
$300
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 12/2411:20 am -
2 stops9h 25m
Thu 1/71:45 pm -
2 stops6h 55m
Deal found 10/19![Southwest logo]()
$305
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.
Thu 12/34:08 pm -
1 stop7h 05m
Wed 12/98:50 am -
1 stop5h 17m
Deal found 10/18![Delta logo]()
$300
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.
Sat 11/217:10 pm -
1 stop6h 15m
Mon 11/238:25 pm -
1 stop10h 40m
Deal found 10/18![Southwest logo]()
$312
This American Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Mon 1/114:12 pm -
1 stop8h 18m
Fri 1/159:17 pm -
2 stops17h 30m
Deal found 10/20![American Airlines logo]()
$387
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.
Tue 12/14:08 pm -
1 stop5h 37m
Tue 12/87:00 am -
1 stop7h 07m
Deal found 10/18![Delta logo]()
$300
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 12/212:50 pm -
Nonstop2h 50m
Fri 12/48:30 am -
Nonstop2h 30m
Deal found 10/15![Southwest logo]()
$315
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.
Wed 12/24:08 pm -
2 stops8h 48m
Wed 12/98:50 am -
1 stop5h 17m
Deal found 10/18![Delta logo]()
$310
This United 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:30 pm -
2 stops8h 31m
Thu 11/56:05 am -
1 stop5h 00m
Deal found 10/19![Multiple Airlines logo]()
$927
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 11/191:20 pm -
2 stops7h 25m
Sun 11/228:25 pm -
1 stop10h 40m
Deal found 10/16![Southwest logo]()
$318
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.
Tue 4/134:30 pm -
1 stop6h 05m
Tue 4/205:30 am -
2 stops9h 17m
Deal found 10/18![Delta logo]()
$310
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 11/92:25 pm -
1 stop6h 45m
Fri 11/136:45 pm -
Nonstop2h 20m
Deal found 10/15![Southwest logo]()
$325
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 10/304:10 pm -
2 stops8h 47m
Tue 11/310:05 am -
1 stop4h 22m
Deal found 10/15![Delta logo]()
$310
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 11/122:30 pm -
1 stop8h 30m
Sat 11/1410:05 am -
2 stops8h 25m
Deal found 10/19![Southwest logo]()
$330
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.
Wed 11/254:35 pm -
Nonstop3h 09m
Mon 1/47:00 am -
Nonstop2h 28m
Deal found 10/16![Delta logo]()
$327
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.
Wed 11/45:55 pm -
Nonstop2h 45m
Thu 11/57:50 am -
Nonstop2h 20m
Deal found 10/16![Southwest logo]()
$335
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 4/77:30 am -
Nonstop2h 45m
Thu 4/81:05 pm -
Nonstop2h 20m
Deal found 10/19![Southwest logo]()
$335
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 11/47:10 pm -
Nonstop2h 56m
Sat 11/712:00 pm -
Nonstop2h 32m
Deal found 10/19![Delta logo]()
$335
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.
Wed 12/27:30 am -
Nonstop3h 08m
Wed 12/98:50 am -
1 stop4h 30m
Deal found 10/18![Delta logo]()
$345
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.
Tue 1/58:10 pm -
Nonstop2h 54m
Tue 1/126:00 am -
1 stop7h 05m
Deal found 10/18![Delta logo]()
$345
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:00 am -
3 stops25h 15m
Sun 12/610:38 am -
3 stops26h 17m
Deal found 10/20![Multiple Airlines logo]()
$945
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.
Mon 3/297:30 am -
Nonstop3h 03m
Thu 4/17:00 am -
1 stop5h 21m
Deal found 10/19![Delta 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 12/98:59 pm -
Nonstop2h 58m
Sat 12/129:59 am -
1 stop7h 36m
Deal found 10/15![Delta logo]()
$345
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 11/84:10 pm -
1 stop7h 07m
Tue 11/105:30 am -
2 stops8h 49m
Deal found 10/18![Delta logo]()
$346
Last-minute flights from Massachusetts to ChicagoDiscover last-minute flight deals from Massachusetts to Chicago. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Chicago. Data last updated October 20, 2026 and is based on user searches.
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.
Mon 11/94:20 pm -
Nonstop2h 45m
Wed 11/118:30 am -
Nonstop2h 30m
Deal found 10/19![Southwest logo]()
$213
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.
Mon 11/97:05 am -
Nonstop2h 45m
Tue 11/101:15 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$214
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:39 pm -
1 stop6h 51m
Fri 11/131:00 pm -
Nonstop2h 49m
Deal found 10/19![Multiple Airlines logo]()
$224
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 11/128:40 pm -
Nonstop2h 56m
Mon 11/167:45 pm -
Nonstop2h 23m
Deal found 10/19![Delta logo]()
$213
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 11/128:16 am -
Nonstop3h 14m
Mon 11/163:16 pm -
Nonstop2h 33m
Deal found 10/19![American Airlines logo]()
$214
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 11/126:30 pm -
Nonstop2h 45m
Mon 11/166:00 am -
1 stop7h 30m
Deal found 10/19![Southwest 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.
Thu 11/124:35 pm -
Nonstop3h 09m
Sat 11/145:42 pm -
1 stop5h 02m
Deal found 10/19![Delta logo]()
$223
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop8h 03m
Wed 11/181:00 pm -
Nonstop2h 49m
Deal found 10/19![Multiple Airlines logo]()
$212
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop7h 20m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 10/16![Frontier logo]()
$220
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 11/1712:15 pm -
1 stop7h 15m
Wed 12/21:19 pm -
1 stop19h 52m
Deal found 10/19![Frontier logo]()
$218
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.
Wed 11/1812:39 pm -
1 stop12h 08m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$218
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.
Thu 11/1912:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/19![Frontier logo]()
$215
One-way flights from Massachusetts to ChicagoSearch for one-way flight options from Massachusetts to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Massachusetts to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Jetabroad 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:05 pm -
Nonstop3h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![JetBlue logo]()
$111
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.
Sat 11/711:27 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$112
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:41 pm -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$112
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.
Wed 11/1112:39 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
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.
Wed 11/2511:06 am -
1 stop29h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![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.
Wed 11/1812:39 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$116
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.
Sat 12/1211:34 am -
1 stop11h 26m
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.
Sat 11/219:15 am -
1 stop4h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$117
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 11/217:00 pm -
1 stop5h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$117
This Super.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/412:39 pm -
1 stop6h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$119
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.
Sat 11/149:30 am -
2 stops8h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$122
This Super.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/412:39 pm -
1 stop12h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$124
Find flight deals from Massachusetts to Chicago
Keep the following information in mind while searching for Massachusetts to Chicago flight deals. Data was last updated October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $212 (Priceline) |
One-way from | $111 (Jetabroad) |
Popular in | October |
Cheapest in | January |
Average price | $328 |
Good round-trip deal | $320 or less |
Good one-way deal | $181 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Chicago 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 Massachusetts to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 11/21
7:10 pm-12:25 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 11/21
9:15 am-12:51 pm
1 stop4h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 12/20
5:45 am-11:37 am
1 stop6h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 12/19
7:10 pm-12:25 am
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 11/21
7:00 pm-11:54 pm
1 stop5h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 11/13
4:20 pm-6:05 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 11/20
8:40 pm-10:36 pm
Nonstop2h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 11/20
4:00 pm-10:18 pm
1 stop7h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 11/23
3:41 pm-10:18 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 12/13
4:59 pm-8:15 pm
1 stop4h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$162
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Massachusetts with our price prediction graph.
BOS-ORD
BOS-MDW
ORH-ORD
MVY-ORD
ACK-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 Massachusetts to Chicago
USMA-CHI
BOS-ORD
BOS-MDW
ORH-ORD
MVY-ORD
What is the cheapest month to book a flight from Massachusetts to Chicago?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $197). Flying from Massachusetts to Chicago in October is currently the most expensive (average of $333). 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 MA to CHI?
Find hourly flight availability from Massachusetts to Chicago. 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.
When flying from Massachusetts to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 34% versus a flight in the afternoon.
Weekly flight availability from Massachusetts to Chicago
Explore weekly flight availability from Massachusetts to Chicago. 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 USMA to CHI are scheduled on a Sunday (74 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (56 on average).
How much does it cost to fly round-trip from Massachusetts to Chicago?
Airfare is below average for this route at the moment.
Massachusetts to Chicago flights typically cost between $216 and $390 in November.The cheapest round-trip price found within the last 5 days was $212 on Multiple Airlines (Nov 14-Nov 18).
How far ahead should I book a flight from Massachusetts to Chicago?
Booking 59 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Chicago. 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 Massachusetts to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Chicago. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Massachusetts to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Massachusetts to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Chicago by cabin class
Find flights from Massachusetts to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Chicago flights
Browse other Massachusetts and Chicago flight options. Last updated on October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Massachusetts to Chicago flights
Consider these flights traveling from Massachusetts to Chicago.
Top 5 airlines flying from Massachusetts to Chicago
Discover the top 5 airlines that operate flights from Massachusetts to Chicago. 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$74 | Average$237 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$294 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$311 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$150 | Average$286 | FlexibilityNo cancel fee | On-time71% |