$129+ Cheap flights from Vermont 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Aug 20 — Aug 271
Round-trip
1 adult, Economy
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Find cheap flights from Vermont to Midway with Cheapflights
1. Tell us where you want to go
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 Vermont to MidwayExplore the most affordable flight options available from Vermont to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 21, 2026.
Explore the most affordable flight options available from Vermont to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 21, 2026.
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/263:05 pm
ALB
- MDW
2 stops8h 15m
Southwest
Sat 8/297:45 am
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/15![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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
ALB
- MDW
1 stop4h 18m
Delta
Mon 10/196:45 pm
MDW
- ALB
1 stop3h 43m
Delta
Deal found 7/15![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/116:05 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Mon 9/146:10 pm
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/17![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 9/268:30 am
ALB
- MDW
2 stops5h 35m
Southwest
Tue 9/292:40 pm
MDW
- ALB
1 stop4h 25m
Southwest
Deal found 7/15![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/226:00 am
ALB
- MDW
2 stops10h 38m
Delta
Wed 8/2612:46 pm
MDW
- ALB
2 stops9h 31m
Delta
Deal found 7/16![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 11/77:00 am
BTV
- MDW
1 stop6h 48m
Delta
Wed 11/116:30 pm
MDW
- BTV
1 stop3h 37m
Delta
Deal found 7/16![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/186:20 pm
ALB
- MDW
Nonstop2h 05m
Southwest
Tue 8/258:30 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 7/19![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/1812:05 pm
BTV
- MDW
2 stops7h 28m
Delta
Tue 8/2510:54 am
MDW
- BTV
2 stops11h 22m
Delta
Deal found 7/20![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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
Tue 9/89:20 am
MDW
- BDL
1 stop6h 35m
Southwest
Deal found 7/17![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/176:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Mon 8/247:10 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/19![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/58:25 am
BDL
- MDW
2 stops9h 40m
Southwest
Mon 9/77:10 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/17![Southwest logo]()
$306
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/511:45 am
BDL
- MDW
2 stops8h 35m
Southwest
Wed 9/912:45 pm
MDW
- BDL
2 stops7h 25m
Southwest
Deal found 7/16![Southwest logo]()
$307
Best flights from Vermont to MidwayDiscover carefully curated flight deals from Vermont to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 21, 2026.
Discover carefully curated flight deals from Vermont to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 21, 2026.
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/263:05 pm
ALB
- MDW
2 stops8h 15m
Southwest
Sat 8/297:45 am
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/15![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/20![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/195:14 am
BTV
- MDW
1 stop7h 37m
Delta
Thu 8/279:24 am
MDW
- BTV
1 stop5h 38m
Delta
Deal found 7/20![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/275:25 am
ALB
- MDW
2 stops7h 55m
Southwest
Sat 8/296:05 am
MDW
- ALB
2 stops8h 45m
Southwest
Deal found 7/15![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/187:15 am
BTV
- MDW
1 stop6h 24m
Delta
Wed 8/265:10 pm
MDW
- BTV
1 stop5h 34m
Delta
Deal found 7/20![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/16:00 am
ALB
- MDW
1 stop6h 35m
Southwest
Tue 12/11:25 pm
MDW
- ALB
Nonstop1h 50m
Southwest
Deal found 7/20![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/212:35 pm
BTV
- MDW
1 stop6h 26m
Delta
Wed 9/95:37 pm
MDW
- BTV
1 stop4h 56m
Delta
Deal found 7/19![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/191:15 pm
BTV
- MDW
1 stop6h 18m
Delta
Tue 8/255:10 pm
MDW
- BTV
1 stop5h 34m
Delta
Deal found 7/20![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/2910:05 am
BDL
- MDW
2 stops8h 10m
Southwest
Mon 8/315:25 pm
MDW
- BDL
1 stop3h 45m
Southwest
Deal found 7/17![Southwest logo]()
$330
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 11/77:00 am
BTV
- MDW
1 stop6h 48m
Delta
Wed 11/1112:30 pm
MDW
- BTV
2 stops9h 37m
Delta
Deal found 7/16![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Sun 9/66:30 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/17![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/105:14 am
BTV
- MDW
1 stop5h 45m
Delta
Mon 8/171:25 pm
MDW
- BTV
2 stops8h 51m
Delta
Deal found 7/20![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/195:50 am
BDL
- MDW
2 stops8h 15m
Southwest
Tue 9/228:35 am
MDW
- BDL
2 stops5h 15m
Southwest
Deal found 7/17![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/1812:05 pm
BTV
- MDW
2 stops7h 28m
Delta
Thu 8/279:24 am
MDW
- BTV
1 stop5h 38m
Delta
Deal found 7/20![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/308:05 am
MDW
- BDL
Nonstop2h 15m
Southwest
Deal found 7/16![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/45:14 am
BTV
- MDW
1 stop7h 37m
Delta
Sat 8/86:11 am
MDW
- BTV
1 stop6h 39m
Delta
Deal found 7/18![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/17:05 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Sun 10/47:10 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/20![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/51:15 pm
BTV
- MDW
1 stop6h 18m
Delta
Sat 8/86:11 am
MDW
- BTV
2 stops8h 51m
Delta
Deal found 7/18![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/305:45 am
BDL
- MDW
1 stop7h 00m
Southwest
Tue 9/11:00 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/20![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 10/37:30 am
BTV
- MDW
2 stops11h 49m
Delta
Mon 10/55:11 pm
MDW
- BTV
1 stop5h 47m
Delta
Deal found 7/15![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/410:15 am
BDL
- MDW
2 stops6h 15m
Southwest
Sun 9/67:45 am
MDW
- BDL
1 stop6h 35m
Southwest
Deal found 7/17![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/186:00 am
ALB
- MDW
1 stop4h 17m
Delta
Wed 8/261:25 pm
MDW
- ALB
2 stops9h 32m
Delta
Deal found 7/18![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/211:35 am
BDL
- MDW
2 stops8h 40m
Southwest
Mon 10/52:15 pm
MDW
- BDL
1 stop7h 40m
Southwest
Deal found 7/16![Southwest logo]()
$366
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 9/256:23 pm
ALB
- MDW
1 stop5h 22m
Delta
Wed 9/301:19 pm
MDW
- ALB
2 stops8h 40m
Delta
Deal found 7/15![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 9/16:00 am
BDL
- MDW
2 stops8h 05m
Southwest
Fri 9/41:10 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/18![Southwest logo]()
$370
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/133:10 pm
ALB
- MDW
2 stops8h 10m
Southwest
Sun 8/166:15 pm
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/19![Southwest logo]()
$394
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/46:00 am
ALB
- MDW
1 stop4h 17m
Delta
Sat 8/86:11 am
MDW
- ALB
1 stop6h 15m
Delta
Deal found 7/16![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/412:45 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Tue 8/1112:20 pm
MDW
- BDL
1 stop6h 50m
Southwest
Deal found 7/19![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/71:27 pm
ALB
- MDW
1 stop6h 06m
Delta
Mon 8/101:25 pm
MDW
- ALB
2 stops8h 52m
Delta
Deal found 7/20![Delta logo]()
$396
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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.
Sun 9/276:00 am
ALB
- MDW
1 stop4h 07m
Delta
Wed 9/3010:48 am
MDW
- ALB
2 stops11h 11m
Delta
Deal found 7/15![Delta logo]()
$397
Last-minute flights from Vermont to MidwayDiscover last-minute flight deals from Vermont to Midway. Data last updated July 21, 2026 and is based on user searches.
Discover last-minute flight deals from Vermont to Midway. Data last updated July 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/55:30 am
BDL
- MDW
1 stop4h 47m
Delta
Tue 8/116:05 am
MDW
- BDL
1 stop5h 43m
Delta
Deal found 7/15![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/131:40 pm
BDL
- MDW
Nonstop2h 15m
Southwest
Mon 8/178:00 am
MDW
- BDL
1 stop6h 05m
Southwest
Deal found 7/16![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/176:20 pm
BDL
- MDW
Nonstop2h 20m
Southwest
Mon 8/247:10 pm
MDW
- BDL
Nonstop2h 05m
Southwest
Deal found 7/19![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/187:15 am
BTV
- MDW
1 stop6h 24m
Delta
Wed 8/265:10 pm
MDW
- BTV
1 stop5h 34m
Delta
Deal found 7/20![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/186:20 pm
ALB
- MDW
Nonstop2h 05m
Southwest
Tue 8/258:30 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 7/19![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/1812:05 pm
BTV
- MDW
2 stops7h 28m
Delta
Tue 8/2510:54 am
MDW
- BTV
2 stops11h 22m
Delta
Deal found 7/20![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/1812:15 pm
ALB
- MDW
1 stop4h 35m
Southwest
Wed 8/196:20 pm
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/19![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/226:00 am
ALB
- MDW
1 stop4h 17m
Delta
Wed 8/265:10 pm
MDW
- ALB
1 stop5h 47m
Delta
Deal found 7/16![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/223:20 pm
ALB
- MDW
1 stop6h 10m
Southwest
Wed 8/268:30 am
MDW
- ALB
Nonstop2h 05m
Southwest
Deal found 7/16![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/256:00 am
BDL
- MDW
2 stops8h 05m
Southwest
Sat 8/299:05 am
MDW
- BDL
1 stop5h 05m
Southwest
Deal found 7/16![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/263:05 pm
ALB
- MDW
2 stops8h 15m
Southwest
Sat 8/297:45 am
MDW
- ALB
Nonstop2h 00m
Southwest
Deal found 7/15![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/275:25 am
ALB
- MDW
2 stops7h 55m
Southwest
Sat 8/296:05 am
MDW
- ALB
2 stops8h 45m
Southwest
Deal found 7/15![Southwest logo]()
$308
One-way flights from Vermont to MidwaySearch for one-way flight options from Vermont to Midway. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
Search for one-way flight options from Vermont to Midway. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/1512:50 pm
ALB
- MDW
Nonstop2h 10m
Southwest
Deal found 7/16![Southwest logo]()
$129
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/144:10 pm
ALB
- MDW
1 stop6h 10m
Southwest
Deal found 7/16![Southwest logo]()
$139
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/235:50 am
ALB
- MDW
2 stops7h 49m
Delta
Deal found 7/16![Delta logo]()
$144
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” 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 8/116:20 pm
ALB
- MDW
Nonstop2h 05m
Southwest
Deal found 7/18![Southwest logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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.
Sat 8/1512:37 pm
ALB
- MDW
2 stops51h 22m
Allegiant Air
Deal found 7/17![Allegiant Air logo]()
$151
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/55:30 am
BDL
- MDW
1 stop4h 47m
Delta
Deal found 7/15![Delta logo]()
$154
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/101:27 pm
ALB
- MDW
1 stop6h 06m
Delta
Deal found 7/17![Delta logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 10/1511:45 am
ALB
- MDW
2 stops28h 55m
Allegiant Air
Deal found 7/19![Allegiant Air logo]()
$162
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/195:21 pm
BDL
- MDW
1 stop6h 23m
Delta
Deal found 7/19![Delta logo]()
$163
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/165:50 am
ALB
- MDW
2 stops7h 49m
Delta
Deal found 7/20![Delta logo]()
$165
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/188:10 am
BDL
- MDW
2 stops8h 15m
Southwest
Deal found 7/19![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/146:00 am
BDL
- MDW
2 stops29h 58m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$170
Find flight deals from Vermont to Midway
Keep the following information in mind while searching for Vermont to Midway flight deals. Data was last updated July 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $272 (Southwest) |
One-way from | $129 (Southwest) |
Popular in | January |
Cheapest in | September |
Average price | $328 |
Cheapflights Fare Finder
Customize your flight search to find flights from Vermont 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 July 21, 2026.
Use the filters below to find and compare flights from Vermont to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
AlbanyChicago
ALB - MDW
ALBMDW
Albany Intl
Wed 8/26
3:05 pm-10:20 pm
2 stops8h 15m
Chicago Midway
Sat 8/29
7:45 am-10:45 am
Nonstop2h 00m
$272
AlbanyChicago
ALB - MDW
ALBMDW
Albany Intl
Sat 9/5
6:00 am-9:17 am
1 stop4h 17m
Chicago Midway
Sun 9/6
6:05 am-1:26 pm
1 stop6h 21m
$277
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Wed 8/19
5:14 am-11:51 am
1 stop7h 37m
Chicago Midway
Thu 8/27
9:24 am-4:02 pm
1 stop5h 38m
$289
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Tue 8/18
7:15 am-12:39 pm
1 stop6h 24m
Chicago Midway
Wed 8/26
5:10 pm-11:44 pm
1 stop5h 34m
$289
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Wed 9/2
12:35 pm-6:01 pm
1 stop6h 26m
Chicago Midway
Wed 9/9
5:37 pm-11:33 pm
1 stop4h 56m
$289
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Wed 8/19
1:15 pm-6:33 pm
1 stop6h 18m
Chicago Midway
Tue 8/25
5:10 pm-11:44 pm
1 stop5h 34m
$289
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Sat 11/7
7:00 am-12:48 pm
1 stop6h 48m
Chicago Midway
Wed 11/11
12:30 pm-11:07 pm
2 stops9h 37m
$294
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Mon 8/10
5:14 am-9:59 am
1 stop5h 45m
Chicago Midway
Mon 8/17
1:25 pm-11:16 pm
2 stops8h 51m
$294
BurlingtonChicago
BTV - MDW
BTVMDW
Burlington
Tue 8/18
12:05 pm-6:33 pm
2 stops7h 28m
Chicago Midway
Thu 8/27
9:24 am-4:02 pm
1 stop5h 38m
$294
AlbanyChicago
ALB - MDW
ALBMDW
Albany Intl
Thu 8/27
5:25 am-12:20 pm
2 stops7h 55m
Chicago Midway
Sat 8/29
6:05 am-3:50 pm
2 stops8h 45m
$308
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Vermont to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Vermont with our price prediction graph.
ALB-MDW
BTV-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 Vermont to Chicago Midway Airport
USVT-MDW
ALB-MDW
BTV-MDW
BDL-MDW
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Vermont 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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