$96+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Midway with Cheapflights
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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 June 9, 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 June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 8/208:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 8/258:50 am
MDW
- BOS
2 stops7h 15m
Southwest
Deal found 6/8![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/206:35 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 8/2211:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 6/9. 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 7/48:45 am
BOS
- MDW
2 stops9h 25m
Southwest
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/9![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 6/9. 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 7/45:30 am
BOS
- MDW
1 stop4h 25m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/9![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/97:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 6/8. 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/8![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 6/9. 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 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/145:05 am
MDW
- BOS
1 stop6h 40m
Southwest
Deal found 6/9![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/167:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sat 7/47:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 7/55:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/4![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 8/71:15 pm
ALB
- MDW
1 stop4h 00m
Southwest
Mon 8/108:05 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 6/8![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 6/9. 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 7/294:15 pm
ALB
- MDW
1 stop6h 25m
Southwest
Wed 8/128:30 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 6/9![Southwest logo]()
$330
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 June 9, 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 June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 7/36:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am
ALB
- MDW
1 stop4h 07m
Delta
Sun 9/279:30 am
MDW
- ALB
1 stop5h 48m
Delta
Deal found 6/6![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 6/4. 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 6/295:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/4![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/142:35 pm
MDW
- BOS
1 stop7h 10m
Southwest
Deal found 6/8![Southwest logo]()
$203
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/1511:35 am
BOS
- MDW
2 stops6h 25m
Southwest
Sat 7/185:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 6/7![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sat 7/47:00 am
BOS
- MDW
2 stops11h 00m
Southwest
Sun 7/55:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/4![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 6/5. 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.
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/286:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/5![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 6/8. 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/78:40 am
MDW
- BOS
1 stop7h 25m
Southwest
Deal found 6/8![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/184:30 pm
BDL
- MDW
1 stop6h 45m
Delta
Tue 7/215:10 pm
MDW
- BDL
1 stop5h 44m
Delta
Deal found 6/7![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:30 am
BDL
- MDW
1 stop4h 44m
Delta
Wed 7/86:00 am
MDW
- BDL
1 stop5h 45m
Delta
Deal found 6/6![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 6/8. 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 8/268:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Sun 8/307:30 am
MDW
- BOS
1 stop5h 30m
Southwest
Deal found 6/8![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 6/4. 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.
Thu 8/205:30 am
BDL
- MDW
1 stop4h 47m
Delta
Sun 8/236:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Deal found 6/4![Delta logo]()
$423
This Southwest deal was found by Cheapflights users on 6/5. 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 7/2811:35 am
BOS
- MDW
2 stops6h 25m
Southwest
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/5![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 6/8. 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.
Fri 8/75:30 am
BDL
- MDW
1 stop4h 47m
Delta
Mon 8/106:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Deal found 6/8![Delta logo]()
$425
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 10/1612:50 pm
BOS
- MDW
2 stops8h 50m
Southwest
Sun 10/188:25 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 6/8![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/254:50 pm
MDW
- BOS
1 stop5h 50m
Southwest
Deal found 6/7![Southwest logo]()
$276
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 6/305:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 7/31:00 pm
MDW
- BOS
2 stops7h 40m
Southwest
Deal found 6/6![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 6/5. 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 9/411:50 am
ALB
- MDW
Nonstop2h 05m
Southwest
Tue 9/88:30 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 6/5![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 6/5. 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 8/146:05 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Sat 8/159:05 am
MDW
- ALB
1 stop5h 45m
Southwest
Deal found 6/5![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 6/9. 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 7/411:30 am
ALB
- MDW
2 stops5h 50m
Southwest
Tue 7/145:10 am
MDW
- ALB
1 stop6h 10m
Southwest
Deal found 6/9![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 10/225:00 am
ALB
- MDW
1 stop7h 15m
Southwest
Sun 10/257:45 pm
MDW
- ALB
Nonstop1h 50m
Southwest
Deal found 6/6![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 9/256:00 am
ALB
- MDW
2 stops12h 05m
Southwest
Mon 9/286:10 pm
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 6/6![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 6/5. 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 7/78:55 am
BDL
- MDW
1 stop6h 05m
Southwest
Sat 7/117:45 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/5![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 6/5. 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 10/95:15 pm
ALB
- MDW
1 stop8h 15m
Southwest
Mon 10/125:00 am
MDW
- ALB
1 stop6h 00m
Southwest
Deal found 6/5![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 11/61:20 pm
ALB
- MDW
2 stops7h 50m
Southwest
Sun 11/85:05 am
MDW
- ALB
1 stop5h 55m
Southwest
Deal found 6/8![Southwest logo]()
$374
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 11/61:20 pm
ALB
- MDW
2 stops7h 45m
Southwest
Mon 11/97:50 am
MDW
- ALB
2 stops8h 15m
Southwest
Deal found 6/7![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 6/8. 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 10/104:55 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Sun 10/117:45 pm
MDW
- ALB
Nonstop1h 50m
Southwest
Deal found 6/8![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 6/9. 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 7/177:10 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Tue 7/217:50 am
MDW
- BDL
Nonstop2h 10m
Southwest
Deal found 6/9![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/184:25 pm
BDL
- MDW
1 stop8h 20m
Southwest
Sat 7/256:30 am
MDW
- BDL
1 stop7h 30m
Southwest
Deal found 6/7![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/223:50 pm
BDL
- MDW
Nonstop2h 25m
Southwest
Sun 8/238:05 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 6/6![Southwest logo]()
$383
Last-minute flights from Massachusetts to MidwayDiscover last-minute flight deals from Massachusetts to Midway. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Midway. Data last updated June 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/8. 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 6/5. 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/5![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/97:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 6/9. 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 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 7/55:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/9![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/48:45 am
BOS
- MDW
2 stops6h 50m
Southwest
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/7![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 6/9. 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 7/47:35 am
BOS
- MDW
1 stop7h 50m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/9![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 6/9. 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 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/145:05 am
MDW
- BOS
1 stop6h 40m
Southwest
Deal found 6/9![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/9. 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 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/92:30 pm
MDW
- BOS
1 stop8h 40m
Southwest
Deal found 6/9![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/115:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 7/137:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$200
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/167:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 6/9. 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 7/294:15 pm
ALB
- MDW
1 stop6h 25m
Southwest
Wed 8/128:30 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 6/9![Southwest logo]()
$330
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 June 9, 2026.
Search for one-way flight options from Massachusetts to Midway. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/7![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 6/8. 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 9/28:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Deal found 6/8![Southwest logo]()
$98
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/148:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/7![Southwest logo]()
$99
This Southwest deal was found by Cheapflights users on 6/8. 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.
Mon 8/108:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/8![Southwest logo]()
$101
This Southwest deal was found by Cheapflights users on 6/8. 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.
Tue 9/112:50 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Deal found 6/8![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 7/235:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/8![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 6/9. 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 7/215:25 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 6/9![Southwest logo]()
$106
This Southwest deal was found by Cheapflights users on 6/4. 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.
Thu 7/27:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/4![Southwest logo]()
$108
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sat 7/45:30 am
BOS
- MDW
1 stop4h 25m
Southwest
Deal found 6/4![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 6/9. 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 8/225:30 am
BOS
- MDW
1 stop5h 00m
Southwest
Deal found 6/9![Southwest logo]()
$110
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/16:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 6/7![Frontier logo]()
$112
This Delta deal was found by Cheapflights users on 6/8. 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 9/86:00 am
ALB
- MDW
1 stop3h 42m
Delta
Deal found 6/8![Delta logo]()
$114
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 June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Southwest) |
One-way from | $96 (Southwest) |
Popular in | May |
Cheapest in | September |
Average price | $247 |
Good round-trip deal | $256 or less |
Good one-way deal | $174 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 June 9, 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
Fri 7/3
6:45 pm-8:35 pm
Nonstop2h 50m
Chicago Midway
Mon 7/6
7:35 pm-10:55 pm
Nonstop2h 20m
$187
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 6/29
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Tue 7/7
2:40 pm-6:00 pm
Nonstop2h 20m
$196
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/7
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Tue 7/14
2:35 pm-10:45 pm
1 stop7h 10m
$203
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 7/15
11:35 am-5:00 pm
2 stops6h 25m
Chicago Midway
Sat 7/18
5:45 pm-9:10 pm
Nonstop2h 25m
$208
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/4
7:00 am-5:00 pm
2 stops11h 00m
Chicago Midway
Sun 7/5
5:15 am-8:25 am
Nonstop2h 10m
$211
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/25
5:20 am-6:55 am
Nonstop2h 35m
Chicago Midway
Tue 7/28
6:05 pm-9:25 pm
Nonstop2h 20m
$212
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 7/1
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Tue 7/7
8:40 am-5:05 pm
1 stop7h 25m
$234
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 8/26
8:15 am-1:30 pm
2 stops6h 15m
Chicago Midway
Sun 8/30
7:30 am-2:00 pm
1 stop5h 30m
$266
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/28
11:35 am-5:00 pm
2 stops6h 25m
Chicago Midway
Fri 7/31
7:35 pm-10:55 pm
Nonstop2h 20m
$267
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 10/16
12:50 pm-8:40 pm
2 stops8h 50m
Chicago Midway
Sun 10/18
8:25 am-11:55 am
Nonstop2h 30m
$273
Showing 1-10 of 60 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, October is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $67). Flying from Massachusetts to Chicago Midway Airport in June is currently the most expensive (average of $157). 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 June 9, 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?
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 84 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 June 8, 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. Saturday evenings 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
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Massachusetts to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
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 June 9, 2026.
Massachusetts and Midway flights
Browse other Massachusetts and Midway flight options. Last updated on June 9, 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 3 airlines flying from Massachusetts to Midway
Discover the top 3 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$183 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$279 | FlexibilityNo cancel fee | On-time63% |