$68+ Cheap flights from Midway (MDW) 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BOS
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Midway to Massachusetts with Cheapflights
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Cheapest flights from Midway to MassachusettsExplore the most affordable flight options available from Midway to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Midway to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/33:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 4/46:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/166:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 2/205:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/9![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/1410:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 3/172:00 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/11![Southwest logo]()
$136
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sun 2/156:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 3/42:40 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/2611:15 am
MDW
- BOS
1 stop4h 40m
Southwest
Thu 4/26:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Deal found 2/9![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/1410:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 2/185:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$145
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sun 2/156:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 2/195:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/274:55 pm
MDW
- BOS
1 stop5h 45m
Southwest
Mon 3/25:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 3/146:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/8![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/37:55 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/57:05 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/9![Southwest logo]()
$152
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/261:25 pm
MDW
- BOS
1 stop9h 25m
Southwest
Thu 3/53:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/12![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/33:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 4/66:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Deal found 2/10![Southwest logo]()
$154
Best flights from Midway to MassachusettsDiscover carefully curated flight deals from Midway to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Midway to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/255:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 3/112:00 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/10![Southwest logo]()
$136
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/159:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Sat 5/168:08 pm
BDL
- MDW
1 stop12h 56m
Frontier
Deal found 2/11![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/116:05 am
MDW
- BDL
2 stops16h 00m
Multiple Airlines
Sun 3/158:08 pm
BDL
- MDW
1 stop19h 13m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/146:34 pm
MDW
- BDL
1 stop3h 38m
Delta
Tue 3/175:04 pm
BDL
- MDW
1 stop6h 27m
Delta
Deal found 2/8![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/2611:15 am
MDW
- BOS
1 stop4h 40m
Southwest
Thu 4/26:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Deal found 2/9![Southwest logo]()
$142
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:00 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 4/57:05 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/8![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 3/146:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/8![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 3/116:00 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$157
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Thu 5/78:08 pm
BDL
- MDW
1 stop12h 56m
Frontier
Deal found 2/12![Frontier logo]()
$215
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/42:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Mon 3/96:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Deal found 2/11![Southwest logo]()
$162
This Priceline deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Mon 3/167:25 am
MDW
- BDL
1 stop10h 48m
Frontier
Thu 3/191:12 pm
BDL
- MDW
1 stop7h 35m
Frontier
Deal found 2/10![Frontier logo]()
$224
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/108:00 am
MDW
- BOS
Nonstop2h 20m
Southwest
Thu 3/1211:45 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/11![Southwest logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/176:00 am
MDW
- BDL
2 stops11h 11m
Multiple Airlines
Thu 3/191:12 pm
BDL
- MDW
1 stop10h 07m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:00 am
MDW
- ALB
1 stop5h 12m
Delta
Wed 4/156:00 pm
ALB
- MDW
1 stop5h 28m
Delta
Deal found 2/10![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/276:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 3/15:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/10![Southwest logo]()
$167
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
- BDL
1 stop8h 35m
Frontier
Mon 3/210:52 am
BDL
- MDW
1 stop10h 35m
Frontier
Deal found 2/11![Frontier logo]()
$250
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:27 am
MDW
- ALB
1 stop6h 08m
Delta
Wed 4/156:00 pm
ALB
- MDW
1 stop5h 28m
Delta
Deal found 2/10![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/86:00 am
MDW
- ALB
1 stop5h 12m
Delta
Mon 4/136:00 pm
ALB
- MDW
1 stop5h 28m
Delta
Deal found 2/10![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/106:34 pm
MDW
- BDL
1 stop3h 38m
Delta
Wed 3/185:34 am
BDL
- MDW
1 stop4h 19m
Delta
Deal found 2/8![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/246:00 am
MDW
- BDL
1 stop6h 14m
Delta
Wed 3/256:00 am
BDL
- MDW
1 stop8h 25m
Delta
Deal found 2/11![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/1012:55 pm
MDW
- BDL
Nonstop2h 00m
Southwest
Tue 3/177:30 am
BDL
- MDW
Nonstop2h 30m
Southwest
Deal found 2/10![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/113:20 pm
MDW
- ALB
2 stops6h 50m
Southwest
Sat 3/147:10 pm
ALB
- MDW
Nonstop2h 20m
Southwest
Deal found 2/10![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/125:00 pm
MDW
- ALB
1 stop6h 15m
Southwest
Mon 3/167:05 pm
ALB
- MDW
Nonstop2h 20m
Southwest
Deal found 2/9![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/205:50 pm
MDW
- ALB
1 stop4h 25m
Southwest
Thu 4/237:25 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Deal found 2/11![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/165:00 pm
MDW
- ALB
1 stop6h 15m
Southwest
Wed 3/186:15 pm
ALB
- MDW
Nonstop2h 20m
Southwest
Deal found 2/10![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/57:45 am
MDW
- ALB
2 stops8h 15m
Southwest
Mon 3/97:05 pm
ALB
- MDW
Nonstop2h 20m
Southwest
Deal found 2/9![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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
MDW
- ACK
2 stops9h 03m
Delta
Wed 7/2912:01 pm
ACK
- MDW
2 stops7h 30m
Delta
Deal found 2/10![Delta logo]()
$603
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/139:15 pm
MDW
- ALB
1 stop9h 40m
Southwest
Thu 4/167:25 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Deal found 2/9![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/107:45 am
MDW
- ALB
2 stops5h 20m
Southwest
Tue 3/175:30 am
ALB
- MDW
2 stops8h 25m
Southwest
Deal found 2/10![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 7/256:00 am
MDW
- ACK
2 stops9h 03m
Delta
Sat 8/112:01 pm
ACK
- MDW
2 stops7h 30m
Delta
Deal found 2/9![Delta logo]()
$969
Last-minute flights from Midway to MassachusettsDiscover last-minute flight deals from Midway to Massachusetts. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Massachusetts. Data last updated February 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/1410:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 3/172:00 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/11![Southwest logo]()
$136
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/1410:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Fri 2/205:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/9![Southwest logo]()
$145
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sun 2/156:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 3/42:40 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sun 2/156:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 2/185:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/166:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 2/205:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/9![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/185:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 2/225:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/9![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/255:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 3/116:00 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$158
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/261:25 pm
MDW
- BOS
1 stop9h 25m
Southwest
Thu 3/53:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/12![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/274:55 pm
MDW
- BOS
1 stop5h 45m
Southwest
Mon 3/25:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 3/146:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/8![Southwest logo]()
$148
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/95:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Wed 3/116:00 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/2611:15 am
MDW
- BOS
1 stop4h 40m
Southwest
Thu 4/26:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Deal found 2/9![Southwest logo]()
$142
One-way flights from Midway to MassachusettsSearch for one-way flight options from Midway to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Midway to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sun 3/16:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/9![Southwest logo]()
$68
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/118:00 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/11![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/35:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/9![Southwest logo]()
$76
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/266:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/9![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/266:25 am
MDW
- BDL
1 stop6h 07m
Frontier
Deal found 2/9![Frontier logo]()
$79
This CheapOair deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/22:19 pm
MDW
- BOS
1 stop9h 54m
Frontier
Deal found 2/9![Frontier logo]()
$80
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Deal found 2/12![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/56:15 am
MDW
- BOS
1 stop9h 30m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$81
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/185:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/9![Southwest logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/79:14 am
MDW
- BDL
1 stop9h 03m
Frontier
Deal found 2/10![Frontier logo]()
$84
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Sun 4/192:20 pm
MDW
- BOS
1 stop9h 31m
Frontier
Deal found 2/9![Frontier logo]()
$86
This Booking.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3111:19 am
MDW
- BDL
1 stop29h 20m
Frontier
Deal found 2/12![Frontier logo]()
$86
Find flight deals from Midway to Massachusetts
Keep the following information in mind while searching for Midway to Massachusetts flight deals. Data was last updated February 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $132 (Southwest) |
One-way from | $68 (Southwest) |
Popular in | April |
Cheapest in | January |
Average price | $240 |
Good round-trip deal | $167 or less |
Good one-way deal | $78 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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 February 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Massachusetts that are best for you.
Fly from
Midway
Fly to
Massachusetts
Route
Depart
Return
Price
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 2/25
5:35 pm-8:50 pm
Nonstop2h 15m
Boston Logan Intl
Wed 3/11
2:00 pm-3:45 pm
Nonstop2h 45m
$136
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 3/26
11:15 am-4:55 pm
1 stop4h 40m
Boston Logan Intl
Thu 4/2
6:25 pm-8:25 pm
Nonstop3h 00m
$142
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 4/1
8:00 am-11:20 am
Nonstop2h 20m
Boston Logan Intl
Sun 4/5
7:05 am-9:00 am
Nonstop2h 55m
$147
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 3/7
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Sat 3/14
6:30 am-8:20 am
Nonstop2h 50m
$148
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 3/7
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Wed 3/11
6:00 pm-7:50 pm
Nonstop2h 50m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 3/4
2:00 pm-5:10 pm
Nonstop2h 10m
Boston Logan Intl
Mon 3/9
6:25 pm-8:25 pm
Nonstop3h 00m
$162
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 3/10
8:00 am-11:20 am
Nonstop2h 20m
Boston Logan Intl
Thu 3/12
11:45 am-1:35 pm
Nonstop2h 50m
$162
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 2/27
6:05 am-9:25 am
Nonstop2h 20m
Boston Logan Intl
Sun 3/1
5:00 am-6:55 am
Nonstop2h 55m
$167
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Fri 5/15
9:14 am-7:17 pm
1 stop9h 03m
Hartford Bradley Intl
Sat 5/16
8:08 pm-8:04 am
1 stop12h 56m
$215
ChicagoHartford
MDW - BDL
MDWBDL
Chicago Midway
Sat 5/2
9:14 am-7:17 pm
1 stop9h 03m
Hartford Bradley Intl
Thu 5/7
8:08 pm-8:04 am
1 stop12h 56m
$215
Showing 1-10 of 60 results
Best time to book a flight from Midway to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Midway with our price prediction graph.
MDW-BOS
MDW-BDL
MDW-ALB
MDW-ACK
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 Midway Airport to Massachusetts
MDW-USMA
MDW-BOS
MDW-BDL
MDW-ALB
MDW-ACK
What is the cheapest month to book a flight from Chicago Midway Airport to Massachusetts?
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Massachusetts (average of $92). Flying from Chicago Midway Airport to Massachusetts in April is currently the most expensive (average of $188). 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 MDW to MA?
Find hourly flight availability from Midway 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 February 12, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 14% on flights from Chicago Midway Airport to Massachusetts by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Midway to Massachusetts. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons 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 February 12, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Massachusetts have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway 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 Midway to Massachusetts
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Complete your trip
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Midway and Massachusetts flights
Browse other Midway and Massachusetts flight options. Last updated on February 12, 2026.
Popular flight searches
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Midway to Massachusetts flights
Consider these flights traveling from Midway to Massachusetts.
Top airline flying from Midway to Massachusetts
Discover the top airline that operate flights from Midway 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 February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$136 | Average$280 | FlexibilityNo cancel fee | On-time63% |