$97+ Cheap flights from Massachusetts to Midway (MDW)
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Midway with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Massachusetts to MidwayExplore the most affordable flight options available from Massachusetts to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
Explore the most affordable flight options available from Massachusetts to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 9/1510:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Tue 9/156:00 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 8/3![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Wed 10/2812:35 pm
BOS
- MDW
1 stop10h 18m
Multiple Airlines
Mon 11/21:26 pm
MDW
- BOS
1 stop20h 16m
Multiple Airlines
Deal found 8/3![Multiple Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Sat 9/197:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/30![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/2. 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.
Wed 9/163:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/236:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 9/148:15 am
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/30![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Mon 8/315:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 8/3. 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 9/53:55 pm
ALB
- MDW
Nonstop2h 05m
Southwest
Mon 9/78:05 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 8/3![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/295:20 am
ALB
- MDW
2 stops8h 10m
Southwest
Sat 9/57:45 am
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/30![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
ALB
- MDW
1 stop4h 17m
Delta
Sun 9/66:05 am
MDW
- ALB
1 stop6h 21m
Delta
Deal found 8/4![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/3. 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 9/53:50 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Sun 9/68:45 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 8/3![Southwest logo]()
$277
Best flights from Massachusetts to MidwayDiscover carefully curated flight deals from Massachusetts to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from Massachusetts to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 9/1510:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Tue 9/156:00 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 8/3![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/156:23 pm
ALB
- MDW
1 stop5h 21m
Delta
Sat 9/199:29 am
MDW
- ALB
1 stop5h 49m
Delta
Deal found 7/29![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/2. 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 9/128:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Sun 9/276:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/31![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:36 am
ALB
- MDW
1 stop4h 11m
Delta
Fri 10/3010:59 am
MDW
- ALB
1 stop6h 12m
Delta
Deal found 8/3![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 8/3. 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.
Fri 12/45:55 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 12/96:25 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/3![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/1. 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.
Thu 10/155:50 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/209:40 am
MDW
- BOS
2 stops6h 30m
Southwest
Deal found 8/1![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 10/271:05 pm
BOS
- MDW
2 stops7h 25m
Southwest
Wed 10/287:55 am
MDW
- BOS
2 stops7h 10m
Southwest
Deal found 8/3![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 8/1. 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 10/146:00 am
BDL
- MDW
1 stop6h 50m
Delta
Mon 10/195:15 pm
MDW
- BDL
1 stop5h 44m
Delta
Deal found 8/1![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 8/253:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/3![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 8/3. 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.
Fri 8/2112:40 pm
BOS
- MDW
Nonstop2h 30m
Southwest
Tue 8/2512:50 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 8/3![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 8/2. 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.
Tue 9/15:50 pm
BOS
- MDW
1 stop5h 30m
Southwest
Thu 9/35:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:15 am
BOS
- MDW
2 stops5h 50m
Southwest
Mon 9/289:00 am
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 7/31![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 8/2. 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.
Tue 10/276:25 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Fri 10/306:50 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 8/2![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:20 pm
ALB
- MDW
Nonstop2h 05m
Southwest
Thu 10/16:50 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 7/31![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Mon 9/218:45 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/1911:05 am
BDL
- MDW
1 stop9h 40m
Southwest
Mon 9/211:20 pm
MDW
- BDL
2 stops7h 55m
Southwest
Deal found 7/30![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:20 am
ALB
- MDW
Nonstop2h 10m
Southwest
Sun 11/16:55 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 7/31![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/218:05 am
ALB
- MDW
Nonstop2h 10m
Southwest
Sun 10/257:05 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 7/31![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/273:10 pm
ALB
- MDW
2 stops8h 10m
Southwest
Sat 9/59:55 am
MDW
- ALB
2 stops10h 00m
Southwest
Deal found 7/29![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 8/1. 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.
Thu 10/1512:30 pm
ALB
- MDW
2 stops7h 45m
Southwest
Sun 10/187:05 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 8/1![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 12/295:50 am
BDL
- MDW
1 stop7h 15m
Southwest
Tue 12/299:05 pm
MDW
- BDL
1 stop9h 45m
Southwest
Deal found 8/3![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:20 am
BDL
- MDW
2 stops9h 10m
Southwest
Tue 9/158:40 am
MDW
- BDL
2 stops7h 30m
Southwest
Deal found 7/31![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/136:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Tue 9/158:45 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$346
This Southwest deal was found by Cheapflights users on 8/1. 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.
Mon 8/246:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Fri 8/281:10 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 8/1![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2010:15 am
BDL
- MDW
2 stops6h 15m
Southwest
Mon 8/249:20 am
MDW
- BDL
2 stops7h 20m
Southwest
Deal found 7/30![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/36:20 am
BDL
- MDW
2 stops9h 10m
Southwest
Sun 9/61:45 pm
MDW
- BDL
2 stops8h 00m
Southwest
Deal found 7/30![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/278:00 am
BDL
- MDW
Nonstop2h 20m
Southwest
Sun 8/305:00 am
MDW
- BDL
1 stop6h 20m
Southwest
Deal found 7/31![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 8/2. 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.
Thu 9/176:20 am
BDL
- MDW
2 stops9h 10m
Southwest
Sun 9/208:05 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$380
Last-minute flights from Massachusetts to MidwayDiscover last-minute flight deals from Massachusetts to Midway. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Midway. Data last updated August 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Mon 8/315:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/295:20 am
ALB
- MDW
2 stops8h 10m
Southwest
Sat 9/57:45 am
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/30![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 8/3. 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 9/53:55 pm
ALB
- MDW
Nonstop2h 05m
Southwest
Mon 9/78:05 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 8/3![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 8/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
ALB
- MDW
1 stop4h 17m
Delta
Sun 9/66:05 am
MDW
- ALB
1 stop6h 21m
Delta
Deal found 8/3![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/3. 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 9/53:50 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Sun 9/68:45 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 8/3![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 9/148:15 am
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/30![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/30![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 8/3. 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.
Tue 9/1510:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Tue 9/156:00 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 8/3![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Sat 9/197:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/30![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/2. 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.
Wed 9/163:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/236:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 8/3. 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.
Thu 9/1711:50 am
ALB
- MDW
Nonstop2h 05m
Southwest
Mon 9/218:05 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 8/3![Southwest logo]()
$279
One-way flights from Massachusetts to MidwaySearch for one-way flight options from Massachusetts to Midway. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from Massachusetts to Midway. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Super.com deal was found by Cheapflights users on 8/2. 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.
Tue 8/1812:45 pm
BOS
- MDW
1 stop11h 02m
Frontier
Deal found 8/2![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Sun 8/2312:45 pm
BOS
- MDW
1 stop11h 02m
Frontier
Deal found 7/31![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:28 am
BOS
- MDW
1 stop11h 30m
Frontier
Deal found 8/1![Frontier logo]()
$99
This Southwest deal was found by Cheapflights users on 8/3. 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.
Wed 9/910:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 8/3![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 7/30![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:28 am
BOS
- MDW
1 stop11h 30m
Frontier
Deal found 8/2![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/228:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/30![Southwest logo]()
$118
This Expedia deal was found by Cheapflights users on 8/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:59 am
BOS
- MDW
1 stop11h 04m
Frontier
Deal found 8/1![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/2512:54 pm
BOS
- MDW
1 stop5h 57m
Frontier
Deal found 7/30![Frontier logo]()
$121
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/55:50 am
BDL
- MDW
1 stop4h 27m
Delta
Deal found 7/30![Delta logo]()
$149
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/295:50 am
BDL
- MDW
2 stops9h 20m
Southwest
Deal found 7/30![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/311:40 pm
BDL
- MDW
Nonstop2h 15m
Southwest
Deal found 7/31![Southwest logo]()
$158
Find flight deals from Massachusetts to Midway
Keep the following information in mind while searching for Massachusetts to Midway flight deals. Data was last updated August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $207 (Southwest) |
One-way from | $97 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $246 |
Good round-trip deal | $261 or less |
Good one-way deal | $180 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Midway 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 August 4, 2026.
Use the filters below to find and compare flights from Massachusetts to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 9/15
10:05 am-11:35 am
Nonstop2h 30m
Chicago Midway
Tue 9/15
6:00 pm-9:25 pm
Nonstop2h 25m
$207
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 9/12
8:40 am-10:15 am
Nonstop2h 35m
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
$231
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 9/23
10:05 am-11:35 am
Nonstop2h 30m
Chicago Midway
Sun 9/27
6:00 am-9:15 am
Nonstop2h 15m
$231
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 12/4
5:55 pm-7:40 pm
Nonstop2h 45m
Chicago Midway
Wed 12/9
6:25 pm-9:40 pm
Nonstop2h 15m
$245
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 10/15
5:50 am-7:25 am
Nonstop2h 35m
Chicago Midway
Tue 10/20
9:40 am-5:10 pm
2 stops6h 30m
$246
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 10/27
1:05 pm-7:30 pm
2 stops7h 25m
Chicago Midway
Wed 10/28
7:55 am-4:05 pm
2 stops7h 10m
$247
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 8/25
3:20 pm-4:55 pm
Nonstop2h 35m
Chicago Midway
Mon 9/7
5:45 am-9:00 am
Nonstop2h 15m
$255
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 8/21
12:40 pm-2:10 pm
Nonstop2h 30m
Chicago Midway
Tue 8/25
12:50 pm-4:10 pm
Nonstop2h 20m
$255
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 9/1
5:50 pm-10:20 pm
1 stop5h 30m
Chicago Midway
Thu 9/3
5:45 am-9:00 am
Nonstop2h 15m
$255
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 9/23
8:15 am-1:05 pm
2 stops5h 50m
Chicago Midway
Mon 9/28
9:00 am-2:30 pm
1 stop4h 30m
$256
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Massachusetts with our price prediction graph.
BOS-MDW
ALB-MDW
BDL-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Chicago Midway Airport
USMA-MDW
BOS-MDW
ALB-MDW
BDL-MDW
What is the cheapest month to book a flight from Massachusetts to Chicago Midway Airport?
Currently, December is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $137). Flying from Massachusetts to Chicago Midway Airport in November is currently the most expensive (average of $400). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MA to MDW?
Find hourly flight availability from Massachusetts to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 4, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 25% on flights from Massachusetts to Chicago Midway Airport by exploring options for tickets in the evening.
How much does it cost to fly round-trip from Massachusetts to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Massachusetts to Chicago Midway Airport flights typically cost between $208 and $403 in September.The cheapest round-trip price found within the last 5 days was $207 on Southwest (Sep 15-Sep 15).
How far ahead should I book a flight from Massachusetts to Chicago Midway Airport?
The best time to book flights from Massachusetts to Chicago Midway Airport is 30 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Massachusetts to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Midway. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Massachusetts to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Massachusetts to Midway
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Complete your trip
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Search flights from Massachusetts to Midway by cabin class
Find flights from Massachusetts to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 4, 2026.
Massachusetts and Midway flights
Browse other Massachusetts and Midway flight options. Last updated on August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Massachusetts to Midway flights
Consider these flights traveling from Massachusetts to Midway.
Top 4 airlines flying from Massachusetts to Midway
Discover the top 4 airlines that operate flights from Massachusetts to Midway. 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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$285 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$181 | Average$227 | FlexibilityNo cancel fee | On-time71% |