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$99+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap flight deals from Vermont to Midway

Keep the following information in mind while searching for Vermont to Midway flight deals. Data was last updated septiembre 15, 2025.

Round-trip from

$188
(Frontier)

One-way from

$99
(Delta)

Popular in

April

Cheapest in

May

Average price

$294
From Vermont to Chicago Midway
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One-way flight from Vermont to Chicago Midway
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Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Vermont to Midway

Cheapest flights from Vermont to Midway
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 septiembre 15, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/2112:18 pmBDL - MDW
1 stop12h 02mFrontier
lun. 9/228:19 amMDW - BDL
1 stop10h 38mFrontier
Deal found 9/15$188
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.
dom. 11/910:59 amBDL - MDW
1 stop12h 04mFrontier
sáb. 11/1511:36 amMDW - BDL
2 stops21h 06mFrontier
Deal found 9/14$192
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/101:36 pmBDL - MDW
2 stops23h 02mFrontier
vie. 11/141:37 pmMDW - BDL
1 stop19h 40mFrontier
Deal found 9/15$194
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.
dom. 10/55:35 amBDL - MDW
1 stop4h 05mDelta
mar. 10/76:23 pmMDW - BDL
1 stop3h 51mDelta
Deal found 9/14$197
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.
jue. 10/210:30 amBDL - MDW
1 stop6h 28mFrontier
lun. 10/68:19 amMDW - BDL
1 stop10h 38mFrontier
Deal found 9/14$201
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/811:13 amBDL - MDW
1 stop8h 26mFrontier
sáb. 11/151:37 pmMDW - BDL
1 stop19h 05mFrontier
Deal found 9/14$208
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.
dom. 10/55:45 amBDL - MDW
Nonstop2h 25mSouthwest
mar. 10/710:00 amMDW - BDL
Nonstop2h 00mSouthwest
Deal found 9/15$212
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/1610:04 amBDL - MDW
1 stop14h 42mFrontier
dom. 10/1912:09 pmMDW - BDL
2 stops26h 12mFrontier
Deal found 9/15$214
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/36:00 amBDL - MDW
1 stop19h 30mMultiple Airlines
mié. 11/52:06 pmMDW - BDL
1 stop18h 36mMultiple Airlines
Deal found 9/15$216
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.
dom. 11/95:15 amBDL - MDW
Nonstop2h 30mSouthwest
mar. 11/119:20 amMDW - BDL
1 stop9h 45mSouthwest
Deal found 9/14$218
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/268:52 pmBDL - MDW
1 stop13h 59mFrontier
dom. 9/2810:13 amMDW - BDL
1 stop8h 29mFrontier
Deal found 9/13$221
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.
jue. 12/47:05 amBTV - MDW
1 stop6h 29mDelta
lun. 12/86:40 pmMDW - BTV
1 stop3h 40mDelta
Deal found 9/14$229

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 septiembre 15, 2025.
Use the filters below to find and compare flights from Vermont to Chicago Midway Airport that are best for you.

Fly from

Vermont

Fly to

Midway

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

dom. 10/5

5:35 am-8:40 am

1 stop4h 05m

Chicago Midway

mar. 10/7

6:23 pm-11:14 pm

1 stop3h 51m

$197

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

jue. 12/4

7:05 am-12:34 pm

1 stop6h 29m

Chicago Midway

lun. 12/8

6:40 pm-11:20 pm

1 stop3h 40m

$229

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

vie. 10/31

7:14 am-12:28 pm

1 stop6h 14m

Chicago Midway

lun. 11/3

1:08 pm-10:38 pm

2 stops8h 30m

$234

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

sáb. 11/8

7:14 am-5:43 pm

2 stops11h 29m

Chicago Midway

lun. 11/10

1:14 pm-11:57 pm

2 stops9h 43m

$239

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

mar. 11/11

5:40 am-10:10 am

1 stop5h 30m

Chicago Midway

mar. 11/18

6:00 pm-8:50 pm

Nonstop1h 50m

$247

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

lun. 11/17

5:10 am-6:30 am

Nonstop2h 20m

Chicago Midway

mar. 11/18

1:25 pm-4:15 pm

Nonstop1h 50m

$250

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

mar. 9/30

6:03 am-11:48 am

1 stop6h 45m

Chicago Midway

sáb. 10/4

11:00 am-11:40 pm

2 stops11h 40m

$254

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

jue. 10/30

6:00 am-12:28 pm

2 stops7h 28m

Chicago Midway

jue. 11/6

9:35 am-4:35 pm

1 stop6h 00m

$254

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

dom. 10/5

5:45 am-7:10 am

Nonstop2h 25m

Chicago Midway

mar. 10/7

7:55 am-3:40 pm

1 stop6h 45m

$257

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mar. 10/14

7:00 am-2:00 pm

1 stop8h 00m

Chicago Midway

mar. 10/21

10:00 am-1:00 pm

Nonstop2h 00m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 53 results
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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.
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
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.

  • How long is the flight from Vermont to Chicago Midway Airport?

    Airlines like Delta and Southwest fly from Vermont to Chicago Midway Airport in about 4h 05m. The time it takes to get you to your destination can typically vary by up to 1h 25m. There are 773 mi between Vermont and Chicago Midway Airport. This flight may include one or multiple stops.

  • What are the most popular routes from Vermont to Chicago Midway Airport?

    While some choose either Albany Intl - Chicago Midway or Burlington - Chicago Midway, Hartford Bradley Intl - Chicago Midway is the most popular route from Vermont to Chicago Midway Airport.

  • Can I find deals for flights from Vermont to Midway that include hotel bookings?

    Yes. In addition to deals on Vermont to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vermont to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vermont to Midway.

  • Can I find deals for business class flights from Vermont to Midway?

    Yes. Cheapflights offers flight deals from Vermont to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Vermont to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Vermont to Chicago Midway Airport (average of $160). Flying from Vermont to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Vermont to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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