$92+ Cheap flights from Chicago (CHI) to Massachusetts
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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Massachusetts with Cheapflights
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Cheapest flights from Chicago to MassachusettsExplore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
Explore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
This SmartFares deal was found by Cheapflights users on 7/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Fri 8/284:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$185
This SmartFares deal was found by Cheapflights users on 7/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Sun 9/136:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/20![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 7/20. 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.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/20![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This SmartFares deal was found by Cheapflights users on 7/22. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Mon 9/145:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$195
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Sat 10/245:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/21![JetBlue logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 9/309:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Wed 9/305:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/19![JetBlue logo]()
$200
This JetBlue deal was found by Cheapflights users on 7/20. 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 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Priceline deal was found by Cheapflights users on 7/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Sat 8/224:22 pm
ACK
- ORD
1 stop6h 36m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This JetBlue deal was found by Cheapflights users on 7/19. 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.
Tue 9/299:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Tue 9/295:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/19![JetBlue logo]()
$202
This Super.com deal was found by Cheapflights users on 7/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Mon 9/285:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$203
This JetBlue deal was found by Cheapflights users on 7/19. 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 10/39:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sat 10/34:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 7/19![JetBlue logo]()
$204
Best flights from Chicago to MassachusettsDiscover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
Discover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
This JetBlue deal was found by Cheapflights users on 7/20. 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 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This United Airlines deal was found by Cheapflights users on 7/19. 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.
Sun 8/169:40 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Sun 8/239:00 am
BOS
- ORD
Nonstop2h 56m
United Airlines
Deal found 7/19![United Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 7/20. 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 8/63:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Mon 8/108:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/20![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 7/18. 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.
Thu 9/175:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 9/216:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/18![Southwest logo]()
$225
This American Airlines deal was found by Cheapflights users on 7/18. 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 9/511:15 am
ORD
- HYA
Nonstop2h 42m
American Airlines
Tue 9/812:42 pm
HYA
- ORD
1 stop8h 04m
American Airlines
Deal found 7/18![American Airlines logo]()
$290
This Priceline deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:40 am
ORD
- HYA
1 stop4h 33m
Multiple Airlines
Sat 8/151:58 pm
HYA
- ORD
2 stops9h 00m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$397
This JetBlue deal was found by Cheapflights users on 7/20. 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 8/226:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Wed 8/2612:02 pm
ACK
- ORD
1 stop6h 33m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This United Airlines deal was found by Cheapflights users on 7/21. 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 10/16:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Sun 10/46:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/21![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 7/18. 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.
Wed 10/148:10 am
MDW
- BOS
1 stop6h 55m
Southwest
Mon 10/1910:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/18![Southwest logo]()
$226
This JetBlue deal was found by Cheapflights users on 7/20. 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 8/296:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 9/24:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/20![JetBlue logo]()
$209
This JetBlue deal was found by Cheapflights users on 7/23. 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.
Thu 8/206:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Mon 8/244:22 pm
ACK
- ORD
1 stop6h 36m
JetBlue
Deal found 7/23![JetBlue logo]()
$210
This Southwest deal was found by Cheapflights users on 7/22. 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 9/129:55 am
MDW
- BOS
2 stops10h 50m
Southwest
Tue 9/157:15 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/22![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Sat 8/86:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 8/107:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/22![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 7/20. 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.
Tue 7/2810:30 am
ORD
- ORH
1 stop5h 30m
Delta
Wed 8/55:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$266
This Southwest deal was found by Cheapflights users on 7/19. 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 8/277:55 pm
MDW
- BOS
1 stop11h 05m
Southwest
Sun 8/309:05 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/19![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 7/19. 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 9/77:20 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Sat 12/196:33 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 7/19![United Airlines logo]()
$245
This JetBlue deal was found by Cheapflights users on 7/22. 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 9/66:00 am
ORD
- BOS
1 stop8h 15m
JetBlue
Sun 9/137:00 am
BOS
- ORD
Nonstop2h 48m
JetBlue
Deal found 7/22![JetBlue logo]()
$228
This Delta deal was found by Cheapflights users on 7/20. 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.
Tue 7/285:30 am
ORD
- ORH
2 stops10h 30m
Delta
Tue 8/115:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 7/21. 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 8/184:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Mon 8/246:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/21![Southwest logo]()
$245
This JetBlue deal was found by Cheapflights users on 7/22. 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 8/159:40 am
ORD
- BOS
1 stop8h 17m
JetBlue
Wed 8/198:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 7/22![JetBlue logo]()
$228
This Delta deal was found by Cheapflights users on 7/20. 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 7/307:05 am
ORD
- ORH
2 stops8h 55m
Delta
Wed 8/55:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/20. 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 8/39:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Thu 8/65:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 7/20![United Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 7/18. 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 8/111:00 pm
MDW
- BOS
2 stops8h 10m
Southwest
Fri 8/145:25 am
BOS
- MDW
1 stop6h 35m
Southwest
Deal found 7/18![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 7/22. 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 8/410:30 am
ORD
- ORH
1 stop5h 30m
Delta
Mon 8/105:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/22![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 8/96:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/18![United Airlines logo]()
$253
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Fri 9/48:30 pm
ORD
- ACK
1 stop13h 37m
American Airlines
Sun 9/611:17 am
ACK
- ORD
1 stop7h 47m
American Airlines
Deal found 7/19![American Airlines logo]()
$371
This JetBlue deal was found by Cheapflights users on 7/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/89:40 am
ORD
- HYA
1 stop4h 33m
JetBlue
Wed 8/124:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/18![JetBlue logo]()
$237
This Southwest deal was found by Cheapflights users on 7/18. 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 8/83:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 8/157:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/18![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 7/22. 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.
Sun 8/97:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Tue 8/119:06 am
BOS
- ORD
1 stop5h 02m
Delta
Deal found 7/22![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sat 8/17:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 7/18![United Airlines logo]()
$266
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated July 23, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 7/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Fri 8/284:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$185
This Super.com deal was found by Cheapflights users on 7/20. 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.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/20![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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 8/196:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Wed 8/194:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/19![JetBlue logo]()
$203
This Priceline deal was found by Cheapflights users on 7/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Sat 8/224:22 pm
ACK
- ORD
1 stop6h 36m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 7/19. 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.
Thu 8/206:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Mon 8/318:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Deal found 7/19![JetBlue logo]()
$209
This JetBlue deal was found by Cheapflights users on 7/21. 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 8/226:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Wed 8/263:33 pm
ACK
- ORD
1 stop4h 54m
JetBlue
Deal found 7/21![JetBlue logo]()
$209
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This Super.com deal was found by Cheapflights users on 7/20. 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.
Fri 8/285:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 8/315:20 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 7/20![JetBlue logo]()
$206
This JetBlue deal was found by Cheapflights users on 7/20. 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 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 7/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Sat 9/125:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/20![JetBlue logo]()
$207
This JetBlue deal was found by Cheapflights users on 7/21. 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 8/296:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 9/24:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/21![JetBlue logo]()
$209
One-way flights from Chicago to MassachusettsSearch for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This SmartFares deal was found by Cheapflights users on 7/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/21:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/19![JetBlue logo]()
$92
This Super.com deal was found by Cheapflights users on 7/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Deal found 7/18![JetBlue logo]()
$96
This Super.com deal was found by Cheapflights users on 7/20. 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 8/129:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/20![JetBlue logo]()
$97
This Super.com deal was found by Cheapflights users on 7/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/21![JetBlue logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
ORD
- ALB
1 stop27h 20m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$99
This Flysmarter deal was found by Cheapflights users on 7/20. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/20![JetBlue logo]()
$100
This JetBlue deal was found by Cheapflights users on 7/21. 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.
Wed 8/269:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Deal found 7/21![JetBlue logo]()
$100
This JetBlue deal was found by Cheapflights users on 7/19. 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.
Tue 9/89:39 am
ORD
- ACK
1 stop4h 44m
JetBlue
Deal found 7/19![JetBlue logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/19![JetBlue logo]()
$102
This Southwest deal was found by Cheapflights users on 7/21. 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 9/197:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/21![Southwest logo]()
$104
This JetBlue deal was found by Cheapflights users on 7/21. 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.
Wed 9/26:00 am
ORD
- BOS
1 stop7h 49m
JetBlue
Deal found 7/21![JetBlue logo]()
$105
This JetBlue deal was found by Cheapflights users on 7/22. 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 8/189:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Deal found 7/22![JetBlue logo]()
$105
Find flight deals from Chicago to Massachusetts
Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $185 (SmartFares) |
One-way from | $92 (SmartFares) |
Popular in | April |
Cheapest in | January |
Average price | $259 |
Good round-trip deal | $210 or less |
Good one-way deal | $133 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2026.
Use the filters below to find and compare flights from Chicago to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Sat 8/29
9:40 am-4:12 pm
1 stop5h 32m
West Tisbury Martha's Vineyard
Tue 9/1
5:05 pm-9:58 pm
1 stop5h 53m
$200
ChicagoNantucket
ORD - ACK
ORDACK
Chicago O'Hare Intl
Sat 8/22
6:00 am-3:24 pm
1 stop8h 24m
Nantucket Memorial
Wed 8/26
12:02 pm-5:35 pm
1 stop6h 33m
$200
ChicagoHyannis
ORD - HYA
ORDHYA
Chicago O'Hare Intl
Sat 8/29
6:00 am-3:13 pm
1 stop8h 13m
Hyannis Barnstable
Wed 9/2
4:20 pm-9:58 pm
1 stop6h 38m
$209
ChicagoNantucket
ORD - ACK
ORDACK
Chicago O'Hare Intl
Thu 8/20
6:00 am-3:24 pm
1 stop8h 24m
Nantucket Memorial
Mon 8/24
4:22 pm-9:58 pm
1 stop6h 36m
$210
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 8/16
9:40 pm-1:11 am
Nonstop2h 31m
Boston Logan Intl
Sun 8/23
9:00 am-10:56 am
Nonstop2h 56m
$225
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/6
3:19 pm-6:59 pm
Nonstop2h 40m
Boston Logan Intl
Mon 8/10
8:50 pm-10:44 pm
Nonstop2h 54m
$225
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 9/17
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Mon 9/21
6:40 pm-8:20 pm
Nonstop2h 40m
$225
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/1
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Sun 10/4
6:00 am-7:59 am
Nonstop2h 59m
$225
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 10/14
8:10 am-4:05 pm
1 stop6h 55m
Boston Logan Intl
Mon 10/19
10:00 pm-11:35 pm
Nonstop2h 35m
$226
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 9/6
6:00 am-3:15 pm
1 stop8h 15m
Boston Logan Intl
Sun 9/13
7:00 am-8:48 am
Nonstop2h 48m
$228
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chicago with our price prediction graph.
ORD-BOS
ORD-ALB
ORD-MVY
ORD-ACK
MDW-BOS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Massachusetts
CHI-USMA
ORD-BOS
ORD-ALB
ORD-MVY
ORD-ACK
What is the cheapest month to book a flight from Chicago to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $199). Flying from Chicago to Massachusetts in June is currently the most expensive (average of $280). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to MA?
Find hourly flight availability from Chicago to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 23, 2026.
One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 41% on airfare.
Weekly flight availability from Chicago to Massachusetts
Explore weekly flight availability from Chicago to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 23, 2026.
The most flights from CHI to USMA are scheduled on a Wednesday (83 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
How much does it cost to fly round-trip from Chicago to Massachusetts?
How far ahead should I book a flight from Chicago to Massachusetts?
Booking 57 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Massachusetts. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Massachusetts. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated July 23, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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.
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Alternative routes for Chicago to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Massachusetts by cabin class
Find flights from Chicago to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Massachusetts flights
Browse other Chicago and Massachusetts flight options. Last updated on July 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Massachusetts flights
Consider these flights traveling from Chicago to Massachusetts.
Top 5 airlines flying from Chicago to Massachusetts
Discover the top 5 airlines that operate flights from Chicago to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$346 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$282 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$127 | Average$276 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$369 | FlexibilityNo cancel fee | On-time71% |