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$104+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$219
(Delta)

One-way from

$104
(Delta)

Popular in

April

Cheapest in

May

Average price

$375
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 ($3 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 June 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 June 16, 2025.

This Delta deal was found by Cheapflights users on 6/16. 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 7/27:20 amBTV - MDW
1 stop6h 09mDelta
Mon 7/74:22 pmMDW - BTV
1 stop5h 53mDelta
Deal found 6/16$219
This Southwest deal was found by Cheapflights users on 6/14. 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 7/16:00 amBDL - MDW
1 stop4h 00mSouthwest
Tue 7/87:20 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 6/14$225
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 7/15:35 amBDL - MDW
1 stop4h 06mDelta
Tue 7/86:20 pmMDW - BDL
1 stop3h 41mDelta
Deal found 6/14$227
This Delta deal was found by Cheapflights users on 6/16. 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 8/216:00 amALB - MDW
1 stop3h 35mDelta
Tue 8/264:25 pmMDW - ALB
1 stop6h 32mDelta
Deal found 6/16$271
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sun 8/311:45 pmALB - MDW
2 stops7h 10mSouthwest
Wed 9/39:00 amMDW - ALB
1 stop7h 40mSouthwest
Deal found 6/15$274
This FlightHub deal was found by Cheapflights users on 6/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2211:44 amBDL - MDW
1 stop23h 10mFrontier
Sun 8/249:17 amMDW - BDL
1 stop24h 32mFrontier
Deal found 6/14$385

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 June 16, 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

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 7/2

7:20 am-12:29 pm

1 stop6h 09m

Chicago Midway

Mon 7/7

4:22 pm-11:15 pm

1 stop5h 53m

$219

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/1

6:00 am-9:00 am

1 stop4h 00m

Chicago Midway

Tue 7/8

7:20 pm-10:20 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/1

5:35 am-8:41 am

1 stop4h 06m

Chicago Midway

Tue 7/8

6:20 pm-11:01 pm

1 stop3h 41m

$227

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 8/21

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Tue 8/26

4:25 pm-11:57 pm

1 stop6h 32m

$271

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sun 8/31

1:45 pm-7:55 pm

2 stops7h 10m

Chicago Midway

Wed 9/3

9:00 am-5:40 pm

1 stop7h 40m

$274

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/11

9:54 am-6:18 pm

1 stop9h 24m

Chicago Midway

Sun 9/14

8:34 am-12:26 pm

1 stop26h 52m

$381

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/1

7:15 am-8:23 pm

2 stops38h 08m

Chicago Midway

Fri 7/4

10:31 am-6:48 pm

3 stops31h 17m

$479

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/22

5:35 am-8:44 am

1 stop4h 09m

$104

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 7/17

7:20 am-8:40 am

Nonstop2h 20m

$119

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 10/28

5:30 am-6:40 am

Nonstop2h 10m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 18 results
1
2

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Vermont to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
722 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,296 reviews
Southwest
8.0
Very good
4,278 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Vermont to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $104 on Delta. Other airlines that offer cheap prices include Southwest from $119 and Frontier from $158 one-way.

  • 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 Vermont?

Book flights to Vermont if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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