$104+ Cheap flights from Massachusetts to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Sep 24 — Oct 11
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 August 25, 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 August 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:17 am -
1 stop12h 42m
Sat 10/33:50 pm -
1 stop18h 08m
Deal found 8/25![Frontier logo]()
$178
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 9/1512:52 pm -
1 stop6h 31m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/25![Frontier logo]()
$184
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Tue 9/1512:52 pm -
1 stop6h 31m
Sat 9/193:50 pm -
1 stop18h 08m
Deal found 8/24![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:57 pm -
1 stop6h 34m
Fri 10/238:11 pm -
1 stop13h 51m
Deal found 8/24![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/211:36 am -
1 stop12h 23m
Fri 10/98:11 pm -
1 stop13h 51m
Deal found 8/23![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 8/25![Frontier logo]()
$197
This Priceline deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/2411:42 am -
1 stop7h 49m
Thu 10/298:24 pm -
Nonstop2h 44m
Deal found 8/24![Multiple Airlines logo]()
$198
This Vliegwinkel deal was found by Cheapflights users on 8/22. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:54 pm -
1 stop6h 29m
Mon 9/148:24 pm -
Nonstop2h 45m
Deal found 8/22![Multiple Airlines logo]()
$199
This Kissandfly.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:35 am -
1 stop6h 05m
Mon 9/217:30 pm -
Nonstop2h 39m
Deal found 8/25![Frontier logo]()
$200
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Thu 10/111:17 am -
1 stop12h 42m
Wed 10/79:39 am -
Nonstop2h 28m
Deal found 8/24![Multiple Airlines logo]()
$203
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/177:30 am -
Nonstop2h 35m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/25![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/186:45 pm -
Nonstop2h 45m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/21![Southwest logo]()
$226
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 August 25, 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 August 25, 2026.
This Southwest deal was found by Cheapflights users on 8/22. 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.
Mon 9/146:40 pm -
Nonstop2h 45m
Thu 9/175:45 am -
Nonstop2h 15m
Deal found 8/22![Southwest logo]()
$217
This JetBlue deal was found by Cheapflights users on 8/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:00 pm -
Nonstop3h 01m
Sat 9/268:24 pm -
Nonstop2h 45m
Deal found 8/22![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 8/22. 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.
Tue 10/67:30 am -
Nonstop2h 54m
Tue 10/137:10 pm -
Nonstop2h 43m
Deal found 8/22![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/266:05 pm -
1 stop5h 13m
Fri 11/66:59 am -
Nonstop2h 19m
Deal found 8/24![United Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:10 pm -
1 stop19h 51m
Sun 11/1510:30 am -
2 stops23h 25m
Deal found 8/25![Multiple Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1510:05 am -
Nonstop2h 30m
Tue 9/156:00 pm -
Nonstop2h 25m
Deal found 8/25![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/248:50 pm -
Nonstop2h 42m
Mon 9/287:35 am -
Nonstop2h 33m
Deal found 8/23![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/186:45 pm -
Nonstop2h 45m
Tue 9/226:00 pm -
Nonstop2h 25m
Deal found 8/24![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/116:42 pm -
Nonstop2h 58m
Sun 9/137:55 pm -
Nonstop2h 35m
Deal found 8/23![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/22. 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.
Tue 10/204:15 pm -
1 stop5h 28m
Wed 10/218:36 am -
1 stop5h 22m
Deal found 8/22![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 8/22. 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.
Sat 9/125:50 am -
2 stops8h 15m
Mon 9/146:30 pm -
Nonstop2h 25m
Deal found 8/22![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 1/153:18 pm -
1 stop7h 17m
Mon 1/187:00 am -
1 stop6h 37m
Deal found 8/23![Delta logo]()
$241
This JetBlue deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 10/273:55 pm -
1 stop9h 02m
Fri 10/302:42 pm -
1 stop8h 45m
Deal found 8/25![JetBlue logo]()
$301
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 10/96:20 am -
Nonstop2h 33m
Mon 10/127:30 am -
Nonstop2h 09m
Deal found 8/20![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/265:50 am -
Nonstop2h 35m
Fri 11/64:00 pm -
1 stop5h 30m
Deal found 8/24![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 8/21. 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.
Thu 2/188:10 pm -
Nonstop2h 54m
Mon 2/226:50 pm -
Nonstop2h 35m
Deal found 8/21![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/163:20 pm -
Nonstop2h 35m
Sun 9/206:00 am -
Nonstop2h 15m
Deal found 8/24![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/247:35 pm -
1 stop4h 56m
Wed 10/286:15 pm -
Nonstop2h 18m
Deal found 8/24![United Airlines logo]()
$287
This JetBlue deal was found by Cheapflights users on 8/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:00 pm -
1 stop7h 08m
Sun 9/136:00 am -
1 stop8h 24m
Deal found 8/22![JetBlue logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:16 pm -
1 stop17h 38m
Sun 10/2510:20 am -
2 stops23h 35m
Deal found 8/21![Multiple Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/104:20 pm -
1 stop5h 11m
Mon 9/146:40 am -
2 stops7h 57m
Deal found 8/24![Delta logo]()
$256
This JetBlue deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/25:00 pm -
1 stop7h 08m
Sun 10/46:00 am -
1 stop8h 54m
Deal found 8/23![JetBlue logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:55 am -
Nonstop2h 34m
Fri 10/96:10 pm -
Nonstop2h 12m
Deal found 8/22![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:15 pm -
1 stop7h 02m
Tue 10/2710:05 am -
1 stop4h 22m
Deal found 8/20![Delta logo]()
$260
This JetBlue deal was found by Cheapflights users on 8/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:00 pm -
1 stop7h 08m
Sun 9/276:00 am -
1 stop8h 24m
Deal found 8/22![JetBlue logo]()
$318
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/111:10 pm -
1 stop7h 10m
Sun 9/136:00 am -
Nonstop2h 15m
Deal found 8/23![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:15 pm -
1 stop7h 02m
Mon 10/268:36 am -
1 stop5h 51m
Deal found 8/20![Delta logo]()
$260
This JetBlue deal was found by Cheapflights users on 8/20. 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.
Thu 9/105:00 pm -
1 stop7h 08m
Sun 9/136:00 am -
1 stop8h 24m
Deal found 8/20![JetBlue logo]()
$318
This Southwest deal was found by Cheapflights users on 8/21. 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.
Mon 12/2112:45 pm -
1 stop6h 05m
Thu 12/319:40 am -
1 stop6h 10m
Deal found 8/21![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Sat 9/1210:33 am -
1 stop7h 19m
Mon 9/146:15 pm -
Nonstop2h 23m
Deal found 8/20![United Airlines logo]()
$327
Last-minute flights from Massachusetts to ChicagoDiscover last-minute flight deals from Massachusetts to Chicago. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Chicago. Data last updated August 25, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:54 pm -
1 stop6h 29m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/22![Frontier logo]()
$188
This Vliegwinkel deal was found by Cheapflights users on 8/22. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:54 pm -
1 stop6h 29m
Mon 9/148:24 pm -
Nonstop2h 45m
Deal found 8/22![Multiple Airlines logo]()
$199
This CheapOair deal was found by Cheapflights users on 8/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:54 pm -
1 stop6h 29m
Sat 9/193:50 pm -
1 stop18h 08m
Deal found 8/22![Frontier logo]()
$206
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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.
Tue 9/1512:52 pm -
1 stop6h 31m
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/25![Frontier logo]()
$184
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:52 pm -
1 stop6h 31m
Wed 9/169:38 am -
Nonstop2h 28m
Deal found 8/25![Multiple Airlines logo]()
$207
This Priceline deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1512:52 pm -
1 stop6h 31m
Thu 9/178:24 pm -
Nonstop2h 45m
Deal found 8/25![Multiple Airlines logo]()
$208
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/165:00 pm -
Nonstop3h 01m
Sat 9/193:50 pm -
1 stop18h 08m
Deal found 8/24![Multiple Airlines logo]()
$203
This Kissandfly.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:35 am -
1 stop6h 05m
Mon 9/217:30 pm -
Nonstop2h 39m
Deal found 8/25![Frontier logo]()
$200
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/177:30 am -
Nonstop2h 35m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/25![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/186:45 pm -
Nonstop2h 45m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/21![Southwest logo]()
$226
This CheapOair deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 8/25![Frontier logo]()
$197
This Priceline deal was found by Cheapflights users on 8/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Wed 9/239:38 am -
Nonstop2h 28m
Deal found 8/22![Multiple Airlines logo]()
$198
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 August 25, 2026.
Search for one-way flight options from Massachusetts to Chicago. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/3012:39 pm -
1 stop12h 08m
Deal found 8/23![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 8/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:36 am -
1 stop12h 23m
Deal found 8/22![Frontier logo]()
$104
This Faresmojo deal was found by Cheapflights users on 8/21. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:50 pm -
Nonstop2h 54m
Deal found 8/21![JetBlue logo]()
$105
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Fri 9/1112:54 pm -
1 stop5h 57m
Deal found 8/24![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Thu 9/1012:54 pm -
1 stop6h 29m
Deal found 8/24![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/165:15 am -
1 stop5h 43m
Deal found 8/25![JetBlue logo]()
$107
This Priceline deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1212:54 pm -
1 stop5h 57m
Deal found 8/25![Frontier logo]()
$108
This Priceline deal was found by Cheapflights users on 8/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/21![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:45 am -
1 stop28h 00m
Deal found 8/22![Multiple Airlines logo]()
$109
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/1510:05 am -
Nonstop2h 30m
Deal found 8/25![Southwest logo]()
$109
This United Airlines deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” 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 9/286:00 am -
Nonstop2h 59m
Deal found 8/25![United Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:55 am -
1 stop28h 41m
Deal found 8/21![Multiple Airlines logo]()
$110
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 August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 (Cheapflightsfares) |
One-way from | $104 (Frontier) |
Popular in | June |
Cheapest in | January |
Average price | $254 |
Good round-trip deal | $278 or less |
Good one-way deal | $175 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 August 25, 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
Mon 9/14
6:40 pm-8:25 pm
Nonstop2h 45m
Chicago Midway
Thu 9/17
5:45 am-9:00 am
Nonstop2h 15m
$217
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 9/22
5:00 pm-7:01 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sat 9/26
8:24 pm-12:09 am
Nonstop2h 45m
$217
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 10/6
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Tue 10/13
7:10 pm-10:53 pm
Nonstop2h 43m
$217
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Tue 9/15
10:05 am-11:35 am
Nonstop2h 30m
Chicago Midway
Tue 9/15
6:00 pm-9:25 pm
Nonstop2h 25m
$217
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 9/24
8:50 pm-10:32 pm
Nonstop2h 42m
Chicago O'Hare Intl
Mon 9/28
7:35 am-11:08 am
Nonstop2h 33m
$217
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 9/18
6:45 pm-8:30 pm
Nonstop2h 45m
Chicago Midway
Tue 9/22
6:00 pm-9:25 pm
Nonstop2h 25m
$226
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Tue 10/20
4:15 pm-8:43 pm
1 stop5h 28m
Chicago O'Hare Intl
Wed 10/21
8:36 am-2:58 pm
1 stop5h 22m
$232
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 9/12
5:50 am-1:05 pm
2 stops8h 15m
Chicago Midway
Mon 9/14
6:30 pm-9:55 pm
Nonstop2h 25m
$232
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 10/26
6:05 pm-10:18 pm
1 stop5h 13m
Chicago O'Hare Intl
Fri 11/6
6:59 am-10:18 am
Nonstop2h 19m
$236
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 10/26
5:50 am-7:25 am
Nonstop2h 35m
Chicago Midway
Fri 11/6
4:00 pm-10:30 pm
1 stop5h 30m
$236
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
BDL-RFD
ORH-ORD
ALB-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
BDL-RFD
ORH-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 $196). Flying from Massachusetts to Chicago in June is currently the most expensive (average of $275). 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 August 25, 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 40% 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 August 25, 2026.
The most flights from USMA to CHI are scheduled on a Monday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 $184 and $315 in October.The cheapest round-trip price found within the last 5 days was $178 on Frontier (Oct 1-Oct 3).
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
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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 August 25, 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 August 25, 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 August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$325 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$129 | Average$280 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$295 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$138 | Average$248 | FlexibilityNo cancel fee | On-time71% |