$100+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Oct 22 — Oct 291
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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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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/19. 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.
Tue 10/204:15 pm -
1 stop7h 02m
Wed 10/218:36 am -
1 stop5h 22m
Deal found 9/19![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/18. 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 10/64:15 pm -
1 stop5h 28m
Wed 10/147:00 am -
2 stops6h 58m
Deal found 9/18![Delta logo]()
$214
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/105:05 pm -
1 stop5h 30m
Wed 11/188:10 am -
2 stops6h 40m
Deal found 9/22![Southwest logo]()
$214
This Flysmarter deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:55 am -
Nonstop2h 52m
Mon 10/199:38 am -
Nonstop2h 28m
Deal found 9/21![JetBlue logo]()
$214
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1510:00 pm -
Nonstop2h 40m
Mon 10/195:30 am -
Nonstop2h 25m
Deal found 9/21![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/154:25 pm -
Nonstop2h 55m
Mon 10/197:25 am -
Nonstop2h 35m
Deal found 9/22![Delta logo]()
$215
This JetBlue deal was found by Cheapflights users on 9/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:11 pm -
1 stop6h 57m
Mon 10/58:24 pm -
Nonstop2h 59m
Deal found 9/20![JetBlue logo]()
$216
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:16 pm -
1 stop7h 40m
Wed 10/78:29 am -
1 stop7h 20m
Deal found 9/18![American Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/39:40 am -
Nonstop2h 35m
Tue 10/61:40 pm -
2 stops6h 40m
Deal found 9/17![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/75:35 am -
1 stop8h 55m
Tue 11/108:30 am -
Nonstop2h 30m
Deal found 9/21![Southwest logo]()
$218
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:36 am -
1 stop12h 23m
Mon 10/58:24 pm -
Nonstop2h 59m
Deal found 9/17![Multiple Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 9/19. 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 11/31:20 pm -
2 stops7h 25m
Tue 11/109:40 am -
2 stops8h 25m
Deal found 9/19![Southwest logo]()
$219
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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 11/44:10 pm -
1 stop7h 07m
Tue 11/107:00 am -
1 stop7h 19m
Deal found 9/17![Delta logo]()
$204
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Sat 10/35:16 pm -
1 stop7h 40m
Wed 10/78:29 am -
1 stop7h 20m
Deal found 9/19![American Airlines logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:11 pm -
1 stop6h 57m
Mon 10/58:24 pm -
Nonstop2h 59m
Deal found 9/19![JetBlue logo]()
$217
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 11/115:00 am -
2 stops13h 05m
Fri 11/1312:45 pm -
2 stops8h 50m
Deal found 9/17![Southwest logo]()
$220
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:45 am -
1 stop4h 53m
Mon 10/196:24 pm -
Nonstop2h 35m
Deal found 9/20![United Airlines logo]()
$225
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 12/235:45 am -
Nonstop3h 06m
Wed 12/309:49 pm -
Nonstop2h 29m
Deal found 9/17![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/94:00 pm -
2 stops8h 54m
Thu 11/127:00 am -
1 stop7h 19m
Deal found 9/21![Delta logo]()
$240
This Southwest deal was found by Cheapflights users on 9/17. 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 10/210:00 pm -
Nonstop2h 35m
Tue 10/68:10 am -
1 stop6h 55m
Deal found 9/17![Southwest logo]()
$252
This JetBlue deal was found by Cheapflights users on 9/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:12 pm -
Nonstop3h 02m
Mon 10/196:10 am -
1 stop7h 19m
Deal found 9/19![JetBlue logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/145:45 am -
1 stop4h 53m
Thu 10/159:24 pm -
Nonstop2h 30m
Deal found 9/17![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 9/19. 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 10/164:15 pm -
1 stop7h 02m
Tue 10/207:00 am -
1 stop6h 58m
Deal found 9/19![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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
Sun 11/157:50 am -
Nonstop2h 20m
Deal found 9/21![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 9/19. 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 10/194:15 pm -
1 stop5h 28m
Tue 10/2710:05 am -
1 stop4h 22m
Deal found 9/19![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
Nonstop2h 59m
Fri 10/237:50 pm -
Nonstop2h 34m
Deal found 9/21![United Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/78:10 am -
2 stops10h 15m
Mon 11/96:25 pm -
2 stops12h 55m
Deal found 9/21![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 9/17. 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 10/234:15 pm -
1 stop7h 02m
Tue 10/278:36 am -
1 stop5h 51m
Deal found 9/17![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/179:40 am -
Nonstop2h 35m
Tue 10/206:10 pm -
Nonstop2h 20m
Deal found 9/17![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 9/18. 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 10/74:15 pm -
1 stop5h 28m
Wed 10/147:00 am -
1 stop6h 58m
Deal found 9/18![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 11/33:41 pm -
1 stop7h 37m
Thu 11/56:59 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:50 am -
Nonstop2h 35m
Mon 10/192:50 pm -
2 stops5h 30m
Deal found 9/20![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 9/19. 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 10/214:15 pm -
2 stops8h 42m
Mon 10/266:30 am -
2 stops7h 57m
Deal found 9/19![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/276:00 am -
2 stops9h 54m
Thu 10/296:59 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 9/17. 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 11/135:55 pm -
1 stop8h 15m
Sun 11/158:25 pm -
1 stop10h 55m
Deal found 9/17![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/157:05 am -
Nonstop2h 35m
Fri 10/166:45 pm -
Nonstop2h 20m
Deal found 9/21![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:01 am -
Nonstop2h 59m
Thu 10/227:50 pm -
Nonstop2h 34m
Deal found 9/20![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 -
1 stop5h 37m
Mon 12/78:50 am -
1 stop5h 17m
Deal found 9/21![Delta logo]()
$280
This Expedia deal was found by Cheapflights users on 9/17. 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.
Fri 10/28:10 am -
1 stop11h 51m
Tue 10/68:24 pm -
2 stops19h 45m
Deal found 9/17![Multiple Airlines logo]()
$1,008
This Southwest deal was found by Cheapflights users on 9/19. 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 10/237:30 pm -
1 stop5h 25m
Tue 10/271:40 pm -
2 stops6h 40m
Deal found 9/19![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Thu 10/225:45 am -
1 stop4h 53m
Tue 10/276:00 am -
Nonstop2h 19m
Deal found 9/19![United Airlines logo]()
$312
This JetBlue deal was found by Cheapflights users on 9/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:00 am -
1 stop9h 14m
Mon 10/199:38 am -
1 stop6h 16m
Deal found 9/19![JetBlue logo]()
$538
Last-minute flights from Massachusetts to ChicagoDiscover last-minute flight deals from Massachusetts to Chicago. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Chicago. Data last updated September 22, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:36 am -
1 stop12h 23m
Mon 10/58:24 pm -
Nonstop2h 59m
Deal found 9/17![Multiple Airlines logo]()
$218
This JetBlue deal was found by Cheapflights users on 9/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:11 pm -
1 stop6h 57m
Mon 10/58:24 pm -
Nonstop2h 59m
Deal found 9/20![JetBlue logo]()
$216
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:16 pm -
1 stop7h 40m
Wed 10/78:29 am -
1 stop7h 20m
Deal found 9/18![American Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/39:40 am -
Nonstop2h 35m
Tue 10/61:40 pm -
2 stops6h 40m
Deal found 9/17![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 9/18. 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 10/64:15 pm -
1 stop5h 28m
Wed 10/147:00 am -
2 stops6h 58m
Deal found 9/18![Delta logo]()
$214
This Flysmarter deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:55 am -
Nonstop2h 52m
Mon 10/199:38 am -
Nonstop2h 28m
Deal found 9/21![JetBlue logo]()
$214
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1510:00 pm -
Nonstop2h 40m
Mon 10/195:30 am -
Nonstop2h 25m
Deal found 9/21![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/154:25 pm -
Nonstop2h 55m
Mon 10/197:25 am -
Nonstop2h 35m
Deal found 9/22![Delta logo]()
$215
This Delta deal was found by Cheapflights users on 9/19. 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.
Tue 10/204:15 pm -
1 stop5h 28m
Tue 10/2710:05 am -
1 stop4h 22m
Deal found 9/19![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/19. 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.
Tue 10/204:15 pm -
2 stops8h 42m
Wed 10/217:00 am -
2 stops6h 58m
Deal found 9/19![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 9/18. 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.
Tue 10/2010:15 am -
2 stops10h 25m
Wed 10/211:40 pm -
2 stops6h 40m
Deal found 9/18![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/2711:45 am -
1 stop6h 25m
Wed 10/287:55 am -
2 stops7h 10m
Deal found 9/21![Southwest logo]()
$214
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 September 22, 2026.
Search for one-way flight options from Massachusetts to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Delta deal was found by Cheapflights users on 9/18. 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 10/64:15 pm -
1 stop5h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$100
This Delta deal was found by Cheapflights users on 9/18. 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 10/54:20 pm -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$113
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/313:41 pm -
1 stop7h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$113
This JetBlue deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:55 am -
1 stop5h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![JetBlue logo]()
$115
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/245:15 am -
2 stops13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$116
This Super.com deal was found by Cheapflights users on 9/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:54 pm -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$117
This Southwest deal was found by Cheapflights users on 9/18. 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 11/711:35 am -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$118
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:00 pm -
1 stop5h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$118
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sun 10/117:01 am -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$119
This Frontier deal was found by Cheapflights users on 9/18. 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 11/1712:15 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 9/18. 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 11/1112:39 pm -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 9/19. 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.
Tue 11/312:15 pm -
1 stop7h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$121
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Delta) |
One-way from | $100 (Delta) |
Popular in | October |
Cheapest in | January |
Average price | $259 |
Good round-trip deal | $299 or less |
Good one-way deal | $165 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 September 22, 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
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Tue 10/13
4:15 pm-10:17 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Tue 10/27
4:10 pm-10:17 pm
1 stop7h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Tue 10/6
4:15 pm-8:43 pm
1 stop5h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Wed 10/14
4:15 pm-10:17 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$100
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 10/17
9:40 am-11:15 am
Nonstop2h 35m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 10/16
4:15 pm-10:17 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 10/23
4:15 pm-10:17 pm
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$138
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 11/2
3:30 pm-8:50 pm
1 stop6h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 10/19
7:01 am-9:00 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 12/7
5:55 pm-7:40 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
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.
ORH-ORD
BOS-ORD
BOS-MDW
ACK-ORD
MVY-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
ORH-ORD
BOS-ORD
BOS-MDW
ACK-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 $198). Flying from Massachusetts to Chicago in October is currently the most expensive (average of $285). 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 September 22, 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 36% 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 September 22, 2026.
The most flights from USMA to CHI are scheduled on a Monday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).
How much does it cost to fly round-trip from Massachusetts to Chicago?
Airfare is typical for this route at the moment.
Massachusetts to Chicago flights typically cost between $204 and $363 in November.The cheapest round-trip price found within the last 5 days was $214 on Southwest (Nov 10-Nov 18).
How far ahead should I book a flight from Massachusetts to Chicago?
Booking 14 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
Lansing
Merrillville
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 September 22, 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 September 22, 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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$327 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$287 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$144 | Average$307 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$146 | Average$250 | FlexibilityNo cancel fee | On-time71% |