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$79+ Cheap flights from Midway (MDW) to Vermont

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BTV
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Midway to Vermont

Keep the following information in mind while searching for Midway to Vermont flight deals. Data was last updated September 17, 2025.

Round-trip from

$176
(Priceline)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

July

Average price

$349
From Chicago Midway to Vermont
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One-way flight from Chicago Midway to Vermont
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Highest demand for flights based on searches. 8% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% 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 Midway to Vermont

Cheapest flights from Midway to Vermont
Explore the most affordable flight options available from Midway to Vermont. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:48 amMDW - BDL
1 stop9h 09mFrontier
Sun 9/288:37 pmBDL - MDW
1 stop11h 46mFrontier
Deal found 9/16$176
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:15 amMDW - BDL
1 stop7h 51mFrontier
Sun 11/210:59 amBDL - MDW
1 stop12h 04mFrontier
Deal found 9/16$188
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:12 amMDW - BDL
1 stop25h 29mFrontier
Sun 11/910:59 amBDL - MDW
1 stop12h 04mFrontier
Deal found 9/16$189
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 10/285:04 pmMDW - BDL
1 stop5h 25mDelta
Sun 11/25:30 amBDL - MDW
1 stop4h 10mDelta
Deal found 9/16$197
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:20 amMDW - BDL
1 stop8h 01mFrontier
Sun 10/128:31 pmBDL - MDW
1 stop28h 15mFrontier
Deal found 9/17$200
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.
Thu 10/309:43 pmMDW - BDL
2 stops35h 19mMultiple Airlines
Thu 11/610:42 amBDL - MDW
1 stop8h 57mMultiple Airlines
Deal found 9/15$204
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 11/46:15 pmMDW - BDL
Nonstop2h 10mSouthwest
Tue 11/113:40 pmBDL - MDW
1 stop6h 25mSouthwest
Deal found 9/16$212
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/39:48 amMDW - BDL
1 stop9h 09mFrontier
Fri 10/104:20 pmBDL - MDW
1 stop8h 26mFrontier
Deal found 9/16$221
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.
Wed 10/158:05 amMDW - BDL
1 stop24h 04mMultiple Airlines
Wed 10/228:05 amBDL - MDW
1 stop26h 42mMultiple Airlines
Deal found 9/15$222
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 10/281:15 pmMDW - BDL
Nonstop2h 00mSouthwest
Fri 10/314:40 pmBDL - MDW
Nonstop2h 30mSouthwest
Deal found 9/17$225
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 10/287:35 amMDW - BDL
2 stops7h 05mSouthwest
Thu 10/303:35 pmBDL - MDW
1 stop6h 00mSouthwest
Deal found 9/16$227
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 10/1510:25 amMDW - ALB
Nonstop1h 50mSouthwest
Wed 10/225:30 amALB - MDW
Nonstop2h 10mSouthwest
Deal found 9/15$237

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Vermont 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Vermont that are best for you.

Fly from

Midway

Fly to

Vermont

Route

Depart

Return

Price

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 10/28

5:04 pm-11:29 pm

1 stop5h 25m

Hartford Bradley Intl

Sun 11/2

5:30 am-8:40 am

1 stop4h 10m

$197

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 11/4

6:15 pm-9:25 pm

Nonstop2h 10m

Hartford Bradley Intl

Tue 11/11

3:40 pm-9:05 pm

1 stop6h 25m

$212

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 10/15

8:05 am-9:09 am

1 stop24h 04m

Hartford Bradley Intl

Fri 10/17

4:20 pm-11:46 pm

1 stop8h 26m

$221

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 11/4

6:15 pm-9:25 pm

Nonstop2h 10m

Hartford Bradley Intl

Sat 11/8

5:15 pm-6:45 pm

Nonstop2h 30m

$225

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 10/28

6:10 pm-9:15 pm

Nonstop2h 05m

Hartford Bradley Intl

Sat 11/1

3:45 pm-9:00 pm

1 stop6h 15m

$235

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 11/13

11:55 am-2:55 pm

Nonstop2h 00m

Hartford Bradley Intl

Mon 11/17

5:40 pm-7:10 pm

Nonstop2h 30m

$242

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 10/8

8:05 am-9:09 am

1 stop24h 04m

Hartford Bradley Intl

Fri 10/10

7:49 pm-10:47 pm

2 stops27h 58m

$243

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Mon 11/17

9:20 am-4:15 pm

1 stop5h 55m

Hartford Bradley Intl

Tue 11/18

5:40 pm-7:10 pm

Nonstop2h 30m

$252

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 10/29

9:35 am-4:09 pm

1 stop5h 34m

Hartford Bradley Intl

Thu 10/30

5:30 am-8:40 am

1 stop4h 10m

$255

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Wed 10/15

5:04 pm-11:57 pm

1 stop5h 53m

Albany Intl

Wed 10/22

6:08 am-8:40 am

1 stop3h 32m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 57 results
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Best time to book a flight from Midway to Vermont

Have a flexible travel schedule? Discover the best time to fly to Vermont from Midway 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 Chicago Midway Airport to Vermont
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 Midway to Vermont. 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 Chicago Midway Airport to Vermont?

    There are many flights that can get you from Chicago Midway Airport to Vermont in 2h 10m. Fly via Delta, Southwest, or Frontier to get the fastest option. The distance from Chicago Midway Airport to Vermont is about 773 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Vermont 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 Chicago Midway Airport to Vermont?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Vermont (average of $327). Flying from Chicago Midway Airport to Vermont in December is currently the most expensive (average of $441). 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

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Alternative routes for Midway to Vermont

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