$83+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jun 5 — Jun 121
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 May 6, 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 May 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 8/58:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/128:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/2![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/110:56 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Wed 7/158:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/2![JetBlue logo]()
$165
This flygcity.se deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/246:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$166
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/1![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/96:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/235:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/1![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/306:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 6/67:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/2![American Airlines logo]()
$168
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$170
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/37:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Mon 6/84:15 pm
BOS
- ORD
Nonstop3h 05m
Delta
Deal found 5/1![Delta logo]()
$172
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$172
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 5/248:37 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Deal found 5/1![American Airlines logo]()
$173
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 May 6, 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 May 6, 2026.
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/165:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/289:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sat 8/18:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/2![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/307:05 am
ORD
- ACK
1 stop7h 43m
Delta
Fri 7/312:06 pm
ACK
- ORD
1 stop5h 39m
Delta
Deal found 5/5![Delta logo]()
$290
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 7/411:45 am
ORD
- HYA
Nonstop2h 50m
American Airlines
Sat 7/116:08 pm
HYA
- ORD
1 stop6h 22m
American Airlines
Deal found 5/4![American Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/156:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Wed 7/226:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/2![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/65:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 6/95:50 am
BOS
- MDW
1 stop5h 55m
Southwest
Deal found 5/3![Southwest logo]()
$177
This JetBlue deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Mon 6/296:00 am
ORD
- ACK
1 stop8h 34m
JetBlue
Fri 7/34:30 pm
ACK
- ORD
1 stop6h 00m
JetBlue
Deal found 5/5![JetBlue logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/56:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Thu 6/117:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/3![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/54:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 6/83:55 pm
BOS
- MDW
2 stops5h 45m
Southwest
Deal found 5/5![Southwest logo]()
$192
This Sun Country Air deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:19 pm
ORD
- BDL
1 stop13h 18m
Sun Country Air
Mon 6/1511:37 am
BDL
- ORD
1 stop6h 52m
Sun Country Air
Deal found 5/3![Sun Country Air logo]()
$425
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/59:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Mon 6/88:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/5![United Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 6/167:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Deal found 5/5![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 7/274:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 8/15:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/2910:25 am
ORD
- BOS
Nonstop2h 37m
United Airlines
Sat 5/305:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/1![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 7/247:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/1![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/276:00 am
ORD
- ACK
1 stop4h 27m
Delta
Tue 6/23:00 pm
ACK
- ORD
1 stop7h 36m
Delta
Deal found 5/5![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/97:50 am
MDW
- BOS
2 stops6h 50m
Southwest
Tue 6/165:00 pm
BOS
- MDW
1 stop5h 35m
Southwest
Deal found 5/5![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Fri 6/266:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/4![United Airlines logo]()
$191
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/299:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/56:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/1![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/202:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Sat 5/236:00 am
BOS
- ORD
2 stops10h 30m
Southwest
Deal found 5/4![Southwest logo]()
$212
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 8/226:00 am
ORD
- MVY
1 stop6h 20m
American Airlines
Sat 8/291:52 pm
MVY
- ORD
1 stop6h 30m
American Airlines
Deal found 5/3![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:25 pm
ORD
- ALB
1 stop7h 34m
Delta
Tue 6/3012:27 pm
ALB
- ORD
1 stop5h 18m
Delta
Deal found 5/5![Delta logo]()
$347
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/159:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Mon 5/186:39 pm
BOS
- ORD
Nonstop3h 01m
United Airlines
Deal found 5/1![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/232:30 pm
MDW
- BOS
1 stop8h 35m
Southwest
Mon 7/271:10 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/5![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/216:00 am
ORD
- ACK
1 stop4h 32m
Delta
Wed 7/2912:13 pm
ACK
- ORD
2 stops7h 16m
Delta
Deal found 5/5![Delta logo]()
$351
This JetBlue deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Mon 8/249:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Sat 8/295:05 pm
MVY
- ORD
1 stop5h 50m
JetBlue
Deal found 5/2![JetBlue logo]()
$427
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/235:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
Sat 5/307:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 5/2![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/161:30 pm
ORD
- BOS
1 stop4h 44m
United Airlines
Sat 6/206:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/2![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/1510:10 am
MDW
- BOS
2 stops6h 35m
Southwest
Wed 7/225:25 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 5/5![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/410:59 am
MDW
- BDL
1 stop6h 11m
Delta
Sat 6/61:02 pm
BDL
- MDW
1 stop6h 31m
Delta
Deal found 5/1![Delta logo]()
$375
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated May 6, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This flygcity.se deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/246:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$166
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 5/248:37 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Deal found 5/1![American Airlines logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/3![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$170
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/298:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$174
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/1![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/306:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 6/67:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/2![American Airlines logo]()
$168
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/37:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Mon 6/84:15 pm
BOS
- ORD
Nonstop3h 05m
Delta
Deal found 5/1![Delta logo]()
$172
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/96:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/235:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/1![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$172
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 May 6, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/178:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/4![JetBlue logo]()
$83
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/312:53 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/1![United Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/65:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/1![Southwest logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Tue 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/5![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Tue 6/912:27 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 5/5![Frontier logo]()
$85
This Flysmarter deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Sat 6/131:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Deal found 5/4![JetBlue logo]()
$86
This Super.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/298:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/5![JetBlue logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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.
Mon 6/298:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/5![JetBlue logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:30 pm
MDW
- BOS
1 stop11h 26m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$88
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 5/319:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/1![United Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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 6/135:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/1![Southwest logo]()
$89
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/67:29 pm
ORD
- BOS
Nonstop2h 37m
American Airlines
Deal found 5/2![American Airlines logo]()
$90
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 May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $83 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $227 |
Good round-trip deal | $208 or less |
Good one-way deal | $108 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 May 6, 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
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 6/10
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Tue 6/16
5:35 am-7:10 am
Nonstop2h 35m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/28
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Sat 8/1
8:15 pm-10:15 pm
Nonstop3h 00m
$172
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/15
6:00 am-11:16 am
1 stop4h 16m
Boston Logan Intl
Wed 7/22
6:00 am-7:58 am
Nonstop2h 58m
$177
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 6/6
5:45 pm-9:05 pm
Nonstop2h 20m
Boston Logan Intl
Tue 6/9
5:50 am-10:45 am
1 stop5h 55m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
6:20 pm-9:56 pm
Nonstop2h 36m
Boston Logan Intl
Thu 6/11
7:19 am-9:17 am
Nonstop2h 58m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Mon 6/8
8:15 am-10:12 am
Nonstop2h 57m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/9
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Tue 6/16
7:27 pm-11:26 pm
1 stop4h 59m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/29
10:25 am-2:02 pm
Nonstop2h 37m
Boston Logan Intl
Sat 5/30
5:45 am-9:36 am
1 stop4h 51m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 6/22
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Fri 6/26
6:43 pm-8:40 pm
Nonstop2h 57m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 6/29
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Sun 7/5
6:00 am-7:58 am
Nonstop2h 58m
$191
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chicago with our price prediction graph.
ORD-BOS
MDW-BOS
ORD-ACK
ORD-HYA
ORD-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Massachusetts
CHI-USMA
ORD-BOS
MDW-BOS
ORD-ACK
ORD-HYA
How far ahead should I book a flight from Chicago to Massachusetts?
Booking 71 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 month to book a flight from Chicago to Massachusetts?
Currently, November is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $182). Flying from Chicago to Massachusetts in December is currently the most expensive (average of $283). 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 May 6, 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 45% on airfare.
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 May 2, 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.
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 May 6, 2026.
The most flights from CHI to USMA are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Chicago to Massachusetts?
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 May 6, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Massachusetts by cabin class
Find flights from Chicago to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Massachusetts flights
Browse other Chicago and Massachusetts flight options. Last updated on May 6, 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 6 airlines flying from Chicago to Massachusetts
Discover the top 6 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 May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$413 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$87 | Average$228 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$257 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$121 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$126 | Average$250 | FlexibilityNo cancel fee | On-time63% |