$119+ Cheap flights from Vermont to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Oct 18 — Oct 251
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Vermont to Midway
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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 September 18, 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 September 18, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/241:10 pm -
1 stop6h 35m
Tue 10/271:05 pm -
2 stops8h 15m
Deal found 9/15![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/1412:55 pm -
1 stop4h 10m
Wed 10/217:45 am -
2 stops9h 00m
Deal found 9/14![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 9/16. 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 10/215:35 am -
2 stops8h 50m
Sat 10/246:45 am -
2 stops7h 15m
Deal found 9/16![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 10/275:35 am -
2 stops9h 50m
Sat 10/318:30 am -
2 stops7h 55m
Deal found 9/17![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/1411:35 am -
1 stop5h 55m
Mon 11/1610:20 am -
2 stops9h 30m
Deal found 9/13![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 10/155:35 pm -
1 stop5h 25m
Mon 10/198:55 pm -
1 stop10h 30m
Deal found 9/18![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/175:00 pm -
1 stop6h 33m
Tue 10/2012:49 pm -
1 stop7h 30m
Deal found 9/17![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/219:42 am -
1 stop4h 05m
Mon 10/265:09 pm -
1 stop5h 41m
Deal found 9/17![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 11/116:25 pm -
Nonstop2h 30m
Thu 11/128:00 am -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 10/226:00 am -
1 stop4h 32m
Thu 10/296:44 pm -
1 stop3h 43m
Deal found 9/16![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/267:25 pm -
Nonstop2h 20m
Wed 10/281:10 pm -
Nonstop2h 05m
Deal found 9/14![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 10/285:55 am -
2 stops9h 30m
Fri 10/3012:45 pm -
2 stops7h 20m
Deal found 9/17![Southwest logo]()
$296
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 September 18, 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 September 18, 2026.
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 1/1112:45 pm -
2 stops7h 10m
Wed 1/138:15 am -
2 stops7h 50m
Deal found 9/13![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/2412:55 pm -
1 stop6h 05m
Tue 10/276:44 pm -
1 stop3h 39m
Deal found 9/14![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 1/145:20 pm -
Nonstop2h 20m
Sat 1/167:35 am -
Nonstop1h 55m
Deal found 9/13![Southwest logo]()
$319
This Delta deal was found by Cheapflights users on 9/15. 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 10/3012:55 pm -
1 stop6h 05m
Mon 11/26:44 pm -
1 stop3h 39m
Deal found 9/15![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/17. 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 12/412:25 pm -
2 stops7h 00m
Wed 12/91:15 pm -
2 stops7h 50m
Deal found 9/17![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/711:44 am -
1 stop6h 03m
Wed 11/111:31 pm -
2 stops8h 35m
Deal found 9/14![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/147:50 am -
Nonstop2h 20m
Mon 11/166:00 am -
1 stop5h 10m
Deal found 9/13![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/215:30 am -
1 stop5h 33m
Sat 10/246:04 am -
2 stops8h 34m
Deal found 9/17![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 9/18. 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.
Mon 10/195:35 pm -
1 stop5h 25m
Mon 10/266:50 pm -
Nonstop2h 00m
Deal found 9/18![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/96:00 am -
2 stops11h 18m
Wed 11/181:31 pm -
2 stops8h 35m
Deal found 9/14![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 9/15. 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 10/212:50 pm -
2 stops8h 10m
Sun 10/258:15 am -
2 stops9h 20m
Deal found 9/15![Southwest logo]()
$348
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/2212:55 pm -
1 stop6h 05m
Sat 10/2412:27 pm -
2 stops7h 40m
Deal found 9/15![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 9/15. 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 10/34:50 pm -
Nonstop2h 10m
Mon 10/56:50 pm -
Nonstop2h 00m
Deal found 9/15![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 9/18. 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 10/207:25 am -
1 stop6h 22m
Sat 10/246:04 am -
2 stops8h 34m
Deal found 9/18![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/112:45 pm -
2 stops8h 40m
Tue 11/36:00 am -
1 stop7h 20m
Deal found 9/13![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 9/18. 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.
Fri 12/115:12 am -
1 stop5h 25m
Sun 12/135:14 pm -
1 stop5h 49m
Deal found 9/18![Delta logo]()
$412
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/167:05 pm -
Nonstop2h 20m
Sun 10/187:45 am -
Nonstop2h 10m
Deal found 9/15![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/3012:25 pm -
1 stop5h 05m
Mon 1/41:20 pm -
Nonstop1h 50m
Deal found 9/13![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 12/155:12 am -
1 stop5h 25m
Fri 12/186:41 pm -
1 stop4h 06m
Deal found 9/15![Delta logo]()
$456
This Southwest deal was found by Cheapflights users on 9/15. 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 12/35:40 am -
1 stop4h 20m
Sun 12/67:50 am -
2 stops7h 20m
Deal found 9/15![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 9/16. 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 12/1112:45 pm -
2 stops8h 40m
Sun 12/137:10 pm -
Nonstop2h 00m
Deal found 9/16![Southwest logo]()
$410
This Southwest deal was found by Cheapflights users on 9/15. 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 11/267:30 am -
Nonstop2h 30m
Mon 11/304:50 pm -
1 stop6h 05m
Deal found 9/15![Southwest logo]()
$430
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:15 pm -
1 stop4h 05m
Sun 10/117:45 am -
Nonstop2h 10m
Deal found 9/14![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:35 am -
2 stops8h 50m
Sat 10/104:50 pm -
1 stop4h 00m
Deal found 9/13![Southwest logo]()
$447
This Southwest deal was found by Cheapflights users on 9/17. 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 10/26:50 am -
Nonstop2h 20m
Mon 10/56:45 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$453
This Southwest deal was found by Cheapflights users on 9/16. 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 10/227:15 am -
2 stops8h 45m
Sun 10/257:45 am -
Nonstop2h 10m
Deal found 9/16![Southwest logo]()
$470
Last-minute flights from Vermont to MidwayDiscover last-minute flight deals from Vermont to Midway. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Vermont to Midway. Data last updated September 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/1412:55 pm -
1 stop4h 10m
Wed 10/217:45 am -
2 stops9h 00m
Deal found 9/14![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 10/155:35 pm -
1 stop5h 25m
Mon 10/198:55 pm -
1 stop10h 30m
Deal found 9/18![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 10/175:00 pm -
1 stop6h 33m
Tue 10/2012:49 pm -
1 stop7h 30m
Deal found 9/17![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 9/16. 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 10/206:25 pm -
Nonstop2h 20m
Fri 10/236:45 pm -
Nonstop2h 10m
Deal found 9/16![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 9/16. 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 10/215:35 am -
2 stops8h 50m
Sat 10/246:45 am -
2 stops7h 15m
Deal found 9/16![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/219:42 am -
1 stop4h 05m
Mon 10/265:09 pm -
1 stop5h 41m
Deal found 9/17![Delta logo]()
$292
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 10/226:00 am -
1 stop4h 32m
Thu 10/296:44 pm -
1 stop3h 43m
Deal found 9/16![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 9/15. 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 10/241:10 pm -
1 stop6h 35m
Tue 10/271:05 pm -
2 stops8h 15m
Deal found 9/15![Southwest logo]()
$282
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/267:25 pm -
Nonstop2h 20m
Wed 10/281:10 pm -
Nonstop2h 05m
Deal found 9/14![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 10/275:35 am -
2 stops9h 50m
Sat 10/318:30 am -
2 stops7h 55m
Deal found 9/17![Southwest logo]()
$288
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 10/285:55 am -
2 stops9h 30m
Fri 10/3012:45 pm -
2 stops7h 20m
Deal found 9/17![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/295:50 am -
2 stops10h 05m
Sat 10/311:45 pm -
Nonstop2h 00m
Deal found 9/14![Southwest logo]()
$292
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 September 18, 2026.
Search for one-way flight options from Vermont to Midway. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 11/143:50 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$119
This Delta deal was found by Cheapflights users on 9/18. 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 12/156:00 am -
1 stop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$129
This Southwest deal was found by Cheapflights users on 9/15. 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.
Mon 12/147:50 am -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 9/16. 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 10/277:00 am -
1 stop5h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$139
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 12/171:20 pm -
2 stops10h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$140
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:55 pm -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$140
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:26 pm -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 9/17. 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.
Mon 11/167:50 am -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 9/16. 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 10/275:35 am -
2 stops8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/97:55 am -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$145
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/146:50 am -
2 stops8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$145
This Delta deal was found by Cheapflights users on 9/17. 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.
Wed 10/76:00 am -
1 stop4h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
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 September 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $282 (Southwest) |
One-way from | $119 (Southwest) |
Popular in | January |
Cheapest in | May |
Average price | $332 |
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 7,457,451 searches. Data last updated September 18, 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 Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Sat 11/14
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Tue 11/17
3:05 pm-7:05 pm
1 stop5h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$129
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Wed 11/11
5:40 am-9:00 am
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$140
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 10/27
5:35 am-1:20 pm
2 stops8h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 12/15
5:40 am-12:55 pm
2 stops8h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Wed 12/16
12:30 pm-8:25 pm
2 stops8h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 11/14
5:33 pm-10:54 pm
1 stop6h 21m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
AlbanyChicago
ALB Albany Intl - MDW Chicago Midway
ALBMDW
Albany Intl
Thu 10/8
6:00 am-9:32 am
1 stop4h 32m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$147
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 10/26
7:25 pm-8:45 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 10/16
5:20 pm-10:33 pm
1 stop6h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$178
Showing 1-10 of 54 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
BDL-MDW
BTV-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
BDL-MDW
BTV-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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