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$68+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$225
(Southwest)

One-way from

$68
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$360
Provider with most accurate pricing for Burlington-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Burlington-Chicago (CHI) flights.
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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. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 26, 2025.

This Frontier deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:05 pmBDL - MDW
1 stop11h 07mFrontier
Mon 12/226:15 amMDW - BDL
1 stop8h 14mFrontier
Deal found 11/25$238
This Kiwi.com deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:05 amBDL - MDW
2 stops29h 56mMultiple Airlines
Sun 12/146:37 pmMDW - BDL
1 stop17h 35mMultiple Airlines
Deal found 11/25$241
This Delta deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amBDL - MDW
1 stop6h 55mDelta
Sun 1/186:14 pmMDW - BDL
1 stop4h 26mDelta
Deal found 11/24$245
This Delta deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:42 pmBDL - MDW
1 stop7h 05mDelta
Wed 12/176:40 pmMDW - BDL
1 stop3h 58mDelta
Deal found 11/25$255
This Delta deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:30 amBDL - MDW
1 stop4h 19mDelta
Wed 12/316:08 pmMDW - BDL
1 stop4h 06mDelta
Deal found 11/24$266
This Booking.com deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:59 amBDL - MDW
1 stop8h 43mFrontier
Sun 12/76:37 pmMDW - BDL
1 stop17h 35mFrontier
Deal found 11/24$275
This Southwest deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:50 amALB - MDW
Nonstop2h 25mSouthwest
Sat 12/139:20 amMDW - ALB
1 stop6h 55mSouthwest
Deal found 11/24$279
This Southwest deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:40 pmBDL - MDW
Nonstop2h 30mSouthwest
Thu 12/116:15 pmMDW - BDL
Nonstop2h 10mSouthwest
Deal found 11/25$280
This Southwest deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:40 pmBDL - MDW
Nonstop2h 30mSouthwest
Wed 12/172:30 pmMDW - BDL
2 stops6h 35mSouthwest
Deal found 11/25$285
This Delta deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:43 amBDL - MDW
1 stop3h 51mDelta
Sun 12/146:00 amMDW - BDL
1 stop6h 17mDelta
Deal found 11/24$287
This Kiwi.com deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:05 amBDL - MDW
2 stops29h 56mMultiple Airlines
Thu 12/117:23 pmMDW - BDL
1 stop14h 45mMultiple Airlines
Deal found 11/25$288
This Southwest deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amALB - MDW
1 stop6h 15mSouthwest
Tue 12/166:00 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 11/24$289

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 November 26, 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

Fri 2/13

7:10 pm-8:45 pm

Nonstop2h 35m

Chicago Midway

Sun 2/15

6:50 am-2:50 pm

1 stop7h 00m

$248

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/17

11:25 am-6:40 pm

2 stops8h 15m

Chicago Midway

Sun 1/18

7:50 am-3:00 pm

1 stop6h 10m

$256

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 2/28

7:10 am-12:46 pm

1 stop6h 36m

Chicago Midway

Tue 3/10

6:35 pm-11:03 pm

1 stop3h 28m

$260

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/30

5:30 am-8:49 am

1 stop4h 19m

Chicago Midway

Tue 1/6

9:32 am-4:07 pm

1 stop5h 35m

$266

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/31

5:30 am-8:49 am

1 stop4h 19m

Chicago Midway

Thu 1/1

6:08 pm-11:14 pm

1 stop4h 06m

$266

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 2/26

7:10 am-12:46 pm

1 stop6h 36m

Chicago Midway

Wed 3/4

6:17 pm-11:18 pm

1 stop4h 01m

$274

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 12/13

5:50 am-7:15 am

Nonstop2h 25m

Chicago Midway

Sat 12/13

9:20 am-5:15 pm

1 stop6h 55m

$279

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 2/25

6:49 am-5:45 pm

2 stops11h 56m

Chicago Midway

Wed 3/4

6:17 pm-11:18 pm

1 stop4h 01m

$279

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Mon 3/2

7:10 am-12:46 pm

1 stop6h 36m

Chicago Midway

Mon 3/9

5:38 pm-11:59 pm

1 stop5h 21m

$283

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 4/3

7:10 am-12:29 pm

1 stop6h 19m

Chicago Midway

Sun 4/5

6:35 pm-11:03 pm

1 stop3h 28m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 56 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 Southwest and Delta fly from Vermont to Chicago Midway Airport in about 2h 35m. The time it takes to get you to your destination can typically vary by up to 4h 01m. 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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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