$68+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MDW
Apr 26 — May 31
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 March 27, 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 March 27, 2026.
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 4/147:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 4/2112:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/25![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/1410:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Wed 4/153:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/26![Southwest logo]()
$136
This Priceline deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Tue 4/1412:40 pm
BOS
- MDW
1 stop7h 51m
Frontier
Wed 4/152:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/24![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Thu 5/79:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/26![Southwest logo]()
$146
This CheapOair deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 3/26![Frontier logo]()
$151
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/52:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Thu 5/711:40 am
MDW
- BOS
1 stop5h 25m
Southwest
Deal found 3/26![Southwest logo]()
$155
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Fri 5/85:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 3/24![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 5/37:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/23![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Sat 5/165:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
Deal found 3/23![Southwest logo]()
$159
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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.
Wed 4/812:42 pm
BOS
- MDW
1 stop10h 37m
Frontier
Wed 4/152:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/25![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:40 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Fri 5/112:55 pm
MDW
- ALB
2 stops6h 55m
Southwest
Deal found 3/23![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:40 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Thu 4/306:50 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 3/23![Southwest logo]()
$286
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 March 27, 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 March 27, 2026.
This Delta deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:40 am
BOS
- MDW
1 stop4h 03m
Delta
Tue 5/196:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 3/25![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/811:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Fri 5/155:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 3/24![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 7/212:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/22![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Thu 6/46:00 pm
MDW
- BOS
1 stop4h 25m
Southwest
Deal found 3/26![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/194:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 6/215:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 3/22![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/16:00 pm
ALB
- MDW
1 stop5h 28m
Delta
Tue 5/56:38 pm
MDW
- ALB
1 stop3h 43m
Delta
Deal found 3/24![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:15 am
BOS
- MDW
2 stops13h 00m
Southwest
Mon 5/185:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 3/23![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
BOS
- MDW
1 stop10h 15m
Southwest
Tue 6/27:50 am
MDW
- BOS
2 stops8h 25m
Southwest
Deal found 3/22![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/295:30 am
BDL
- MDW
1 stop4h 17m
Delta
Fri 5/15:21 pm
MDW
- BDL
1 stop5h 38m
Delta
Deal found 3/26![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 6/179:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/22![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
ALB
- MDW
1 stop3h 47m
Delta
Mon 4/276:38 pm
MDW
- ALB
1 stop3h 43m
Delta
Deal found 3/22![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/75:50 pm
BOS
- MDW
1 stop7h 05m
Southwest
Mon 5/112:10 pm
MDW
- BOS
2 stops8h 45m
Southwest
Deal found 3/24![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/215:30 am
BDL
- MDW
1 stop4h 13m
Delta
Tue 5/265:12 pm
MDW
- BDL
1 stop6h 21m
Delta
Deal found 3/26![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 5/34:05 pm
MDW
- BOS
2 stops7h 00m
Southwest
Deal found 3/22![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 5/44:56 pm
BDL
- MDW
1 stop6h 32m
Delta
Sun 5/106:36 pm
MDW
- BDL
1 stop3h 59m
Delta
Deal found 3/24![Delta logo]()
$402
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/308:45 am
BOS
- MDW
2 stops9h 55m
Southwest
Mon 5/42:10 pm
MDW
- BOS
2 stops6h 40m
Southwest
Deal found 3/26![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:30 am
BDL
- MDW
1 stop4h 17m
Delta
Tue 4/216:00 am
MDW
- BDL
1 stop6h 16m
Delta
Deal found 3/23![Delta logo]()
$421
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:20 pm
ALB
- MDW
1 stop4h 10m
Southwest
Fri 4/175:50 pm
MDW
- ALB
1 stop4h 25m
Southwest
Deal found 3/22![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 6/191:15 pm
BDL
- MDW
1 stop6h 16m
Delta
Tue 6/239:17 am
MDW
- BDL
1 stop5h 49m
Delta
Deal found 3/26![Delta logo]()
$428
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:25 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Mon 6/15:00 am
MDW
- ALB
1 stop12h 45m
Southwest
Deal found 3/22![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:45 pm
BOS
- MDW
1 stop5h 00m
Southwest
Sun 5/248:50 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/23![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:20 pm
ALB
- MDW
2 stops8h 05m
Southwest
Thu 4/239:00 am
MDW
- ALB
1 stop6h 40m
Southwest
Deal found 3/23![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:10 am
ALB
- MDW
2 stops8h 20m
Southwest
Wed 5/62:35 pm
MDW
- ALB
2 stops6h 30m
Southwest
Deal found 3/25![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:55 pm
ALB
- MDW
2 stops6h 25m
Southwest
Wed 4/2210:10 am
MDW
- ALB
2 stops6h 50m
Southwest
Deal found 3/23![Southwest logo]()
$345
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/257:00 am
BDL
- MDW
Nonstop2h 25m
Southwest
Mon 4/279:15 pm
MDW
- BDL
1 stop9h 55m
Southwest
Deal found 3/26![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:15 pm
ALB
- MDW
Nonstop2h 15m
Southwest
Sun 6/71:35 pm
MDW
- ALB
Nonstop1h 50m
Southwest
Deal found 3/23![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 5/37:50 am
ALB
- MDW
Nonstop2h 15m
Southwest
Fri 5/86:50 pm
MDW
- ALB
Nonstop1h 55m
Southwest
Deal found 3/26![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:25 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Sun 5/38:20 am
MDW
- ALB
1 stop7h 50m
Southwest
Deal found 3/23![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:35 pm
ALB
- MDW
2 stops8h 30m
Southwest
Mon 5/181:00 pm
MDW
- ALB
2 stops6h 50m
Southwest
Deal found 3/26![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:20 pm
BDL
- MDW
Nonstop2h 30m
Southwest
Mon 5/257:00 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 3/22![Southwest logo]()
$383
Last-minute flights from Massachusetts to MidwayDiscover last-minute flight deals from Massachusetts to Midway. Data last updated March 27, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Midway. Data last updated March 27, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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.
Wed 4/812:42 pm
BOS
- MDW
1 stop10h 37m
Frontier
Wed 4/152:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/25![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/119:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 4/143:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/26![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/136:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 4/147:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/24![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 4/147:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 4/2112:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/25![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/1410:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Wed 4/153:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/26![Southwest logo]()
$136
This Priceline deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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.
Tue 4/1412:40 pm
BOS
- MDW
1 stop7h 51m
Frontier
Wed 4/152:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/24![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 4/1411:40 am
BOS
- MDW
2 stops8h 45m
Southwest
Thu 4/169:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/24![Southwest logo]()
$161
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 4/1510:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 4/199:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/26![Southwest logo]()
$157
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:50 pm
BDL
- MDW
1 stop7h 29m
Frontier
Fri 4/176:00 am
MDW
- BDL
1 stop7h 49m
Frontier
Deal found 3/22![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/163:50 pm
BDL
- MDW
1 stop7h 29m
Multiple Airlines
Tue 4/216:10 am
MDW
- BDL
2 stops11h 01m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 4/225:45 am
BOS
- MDW
1 stop6h 50m
Southwest
Wed 4/299:50 am
MDW
- BOS
1 stop6h 30m
Southwest
Deal found 3/25![Southwest logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/273:50 pm
BDL
- MDW
1 stop7h 29m
Multiple Airlines
Wed 4/297:30 am
MDW
- BDL
2 stops14h 39m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$329
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 March 27, 2026.
Search for one-way flight options from Massachusetts to Midway. Find affordable one-way fares based on user searches. Data last updated March 27, 2026.
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/25![Southwest logo]()
$68
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 4/147:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/25![Southwest logo]()
$69
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 4/233:50 pm
BDL
- MDW
1 stop7h 29m
Frontier
Deal found 3/25![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 3/27![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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.
Mon 5/116:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 3/25![Frontier logo]()
$71
This Expedia deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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.
Sat 5/211:16 am
BOS
- MDW
1 stop21h 25m
Frontier
Deal found 3/25![Frontier logo]()
$76
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/26![Southwest logo]()
$78
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 4/1510:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/25![Southwest logo]()
$79
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” 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 6/115:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 3/24![Southwest logo]()
$81
This Southwest deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” 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 5/122:25 pm
BOS
- MDW
2 stops6h 10m
Southwest
Deal found 3/25![Southwest logo]()
$83
This Southwest deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” 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 6/412:55 pm
BOS
- MDW
1 stop7h 40m
Southwest
Deal found 3/26![Southwest logo]()
$88
This Super.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:55 pm
BDL
- MDW
1 stop6h 12m
Frontier
Deal found 3/25![Frontier logo]()
$89
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 March 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $135 (Southwest) |
One-way from | $68 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $267 |
Good round-trip deal | $306 or less |
Good one-way deal | $171 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 March 27, 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
Sat 5/16
5:40 am-8:43 am
1 stop4h 03m
Chicago Midway
Tue 5/19
6:36 pm-11:29 pm
1 stop3h 53m
$169
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 5/8
11:35 am-5:50 pm
1 stop7h 15m
Chicago Midway
Fri 5/15
5:40 pm-11:10 pm
1 stop4h 30m
$177
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 7/15
3:45 pm-5:30 pm
Nonstop2h 45m
Chicago Midway
Tue 7/21
2:40 pm-6:00 pm
Nonstop2h 20m
$217
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/3
10:45 am-12:25 pm
Nonstop2h 40m
Chicago Midway
Thu 6/4
6:00 pm-11:25 pm
1 stop4h 25m
$230
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 6/19
4:45 pm-6:35 pm
Nonstop2h 50m
Chicago Midway
Sun 6/21
5:15 am-8:25 am
Nonstop2h 10m
$232
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/16
5:15 am-5:15 pm
2 stops13h 00m
Chicago Midway
Mon 5/18
5:40 pm-11:10 pm
1 stop4h 30m
$242
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/30
6:00 am-3:15 pm
1 stop10h 15m
Chicago Midway
Tue 6/2
7:50 am-5:15 pm
2 stops8h 25m
$248
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/10
3:45 pm-5:30 pm
Nonstop2h 45m
Chicago Midway
Wed 6/17
9:00 am-12:15 pm
Nonstop2h 15m
$252
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/7
5:50 pm-11:55 pm
1 stop7h 05m
Chicago Midway
Mon 5/11
2:10 pm-11:55 pm
2 stops8h 45m
$256
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 4/25
1:50 pm-3:30 pm
Nonstop2h 40m
Chicago Midway
Sun 5/3
4:05 pm-12:05 am
2 stops7h 00m
$267
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, June is the cheapest month in which you can book a flight from Massachusetts to Chicago Midway Airport (average of $97). Flying from Massachusetts to Chicago Midway Airport in March is currently the most expensive (average of $165). 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 March 27, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 33% on flights from Massachusetts to Chicago Midway Airport by exploring options for tickets in the evening.
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 March 23, 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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Massachusetts to Chicago Midway Airport?
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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 March 27, 2026.
Massachusetts and Midway flights
Browse other Massachusetts and Midway flight options. Last updated on March 27, 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 2 airlines flying from Massachusetts to Midway
Discover the top 2 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 March 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$274 | FlexibilityNo cancel fee | On-time63% |