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$105+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Frontier)

One-way from

$105
(Frontier)

Popular in

April

Cheapest in

January

Average price

$467
Provider with most accurate pricing for Burlington-Chicago (CHI) flight deals.
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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. 8% potential increase in price ($36 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 April 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 April 1, 2025.

This Frontier deal was found by Cheapflights users on 3/31. 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 5/153:28 pmBDL - MDW
1 stop9h 11mFrontier
Sun 5/1810:55 amMDW - BDL
1 stop7h 19mFrontier
Deal found 3/31$228
This Southwest deal was found by Cheapflights users on 3/31. 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 6/42:40 pmALB - MDW
1 stop7h 40mSouthwest
Sat 6/77:05 pmMDW - ALB
Nonstop1h 55mSouthwest
Deal found 3/31$263
This Delta deal was found by Cheapflights users on 3/30. 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 4/236:05 amALB - MDW
1 stop3h 35mDelta
Tue 4/295:59 pmMDW - ALB
1 stop4h 22mDelta
Deal found 3/30$273
This Booking.com deal was found by Cheapflights users on 3/31. 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 4/46:57 pmBTV - MDW
1 stop28h 39mFrontier
Sun 4/612:46 pmMDW - BTV
1 stop22h 52mFrontier
Deal found 3/31$290
This Delta deal was found by Cheapflights users on 3/31. 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 7/16:00 amBDL - MDW
1 stop6h 56mDelta
Sat 7/55:53 pmMDW - BDL
1 stop4h 03mDelta
Deal found 3/31$293
This Delta deal was found by Cheapflights users on 3/31. 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 5/67:09 amBTV - MDW
1 stop6h 26mDelta
Wed 5/149:16 amMDW - BTV
1 stop5h 53mDelta
Deal found 3/31$294
This Southwest deal was found by Cheapflights users on 3/30. 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 5/275:55 amBDL - MDW
Nonstop2h 25mSouthwest
Fri 5/306:35 pmMDW - BDL
Nonstop2h 05mSouthwest
Deal found 3/30$296

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 April 1, 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

Thu 5/15

3:28 pm-11:39 pm

1 stop9h 11m

Chicago Midway

Sun 5/18

10:55 am-7:14 pm

1 stop7h 19m

$228

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 6/4

2:40 pm-9:20 pm

1 stop7h 40m

Chicago Midway

Sat 6/7

7:05 pm-10:00 pm

Nonstop1h 55m

$263

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 4/23

6:05 am-8:40 am

1 stop3h 35m

Chicago Midway

Tue 4/29

5:59 pm-11:21 pm

1 stop4h 22m

$273

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/1

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Sat 7/5

5:53 pm-10:56 pm

1 stop4h 03m

$293

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Tue 5/6

7:09 am-12:35 pm

1 stop6h 26m

Chicago Midway

Wed 5/14

9:16 am-4:09 pm

1 stop5h 53m

$294

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 5/27

5:55 am-7:20 am

Nonstop2h 25m

Chicago Midway

Fri 5/30

6:35 pm-9:40 pm

Nonstop2h 05m

$296

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/1

3:39 pm-11:39 pm

1 stop9h 00m

$105

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 5/13

6:00 am-7:15 am

Nonstop2h 15m

$113

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 6/3

6:00 am-8:40 am

1 stop3h 40m

$123

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/24

5:50 pm-7:15 pm

Nonstop2h 25m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 14 results
1
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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

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 April 1, 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
4,276 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,276 reviews
Southwest
8.0
Very good
4,276 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $105 on Frontier. Other airlines that offer cheap prices include Southwest from $113 and Delta from $123 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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