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$95+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
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 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$225
(Southwest)

One-way from

$95
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$342
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. 5% potential increase in price ($18 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 12, 2025.

This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 12/117:25 amBDL - MDW
2 stops6h 35mSouthwest
Tue 12/1612:55 pmMDW - BDL
1 stop6h 10mSouthwest
Deal found 11/11$227
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Fri 12/511:59 amBDL - MDW
1 stop27h 00mMultiple Airlines
Mon 12/86:15 amMDW - BDL
2 stops15h 37mMultiple Airlines
Deal found 11/11$228
This Mytrip deal was found by Cheapflights users on 11/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2311:42 amBDL - MDW
1 stop11h 51mFrontier
Thu 11/275:30 pmMDW - BDL
1 stop22h 47mFrontier
Deal found 11/9$229
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Tue 11/255:42 pmBDL - MDW
1 stop24h 15mMultiple Airlines
Tue 12/27:44 amMDW - BDL
2 stops28h 58mMultiple Airlines
Deal found 11/11$234
This Southwest deal was found by Cheapflights users on 11/10. 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 12/165:15 amBDL - MDW
Nonstop2h 30mSouthwest
Wed 12/1712:55 pmMDW - BDL
1 stop6h 10mSouthwest
Deal found 11/10$235
This Delta deal was found by Cheapflights users on 11/10. 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 12/43:54 pmBTV - MDW
2 stops8h 53mDelta
Mon 12/812:50 pmMDW - BTV
2 stops9h 43mDelta
Deal found 11/10$239
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Fri 12/51:19 pmBDL - MDW
1 stop10h 20mMultiple Airlines
Sun 12/76:37 pmMDW - BDL
2 stops27h 15mMultiple Airlines
Deal found 11/10$242
This Delta deal was found by Cheapflights users on 11/11. 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 12/177:30 amBDL - MDW
1 stop5h 25mDelta
Sun 1/186:14 pmMDW - BDL
1 stop4h 26mDelta
Deal found 11/11$245
This Southwest deal was found by Cheapflights users on 11/11. 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 12/165:10 amALB - MDW
Nonstop2h 20mSouthwest
Wed 12/246:00 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 11/11$250
This Delta deal was found by Cheapflights users on 11/11. 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.
Mon 11/246:00 amALB - MDW
1 stop3h 54mDelta
Thu 11/276:00 amMDW - ALB
1 stop6h 13mDelta
Deal found 11/11$251
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2010:54 amBDL - MDW
1 stop12h 49mFrontier
Sat 11/226:02 pmMDW - BDL
1 stop24h 30mFrontier
Deal found 11/11$251
This Mytrip deal was found by Cheapflights users on 11/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:59 amBDL - MDW
1 stop11h 13mFrontier
Sun 12/76:37 pmMDW - BDL
1 stop17h 35mFrontier
Deal found 11/10$252

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 12, 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

Sun 2/22

5:10 am-6:45 am

Nonstop2h 35m

Chicago Midway

Sat 2/28

6:05 pm-9:05 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/11

7:25 am-1:00 pm

2 stops6h 35m

Chicago Midway

Tue 12/16

12:55 pm-8:05 pm

1 stop6h 10m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/8

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Sat 1/10

6:40 am-11:55 am

1 stop4h 15m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/16

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Wed 12/17

12:55 pm-8:05 pm

1 stop6h 10m

$235

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 12/4

3:54 pm-11:47 pm

2 stops8h 53m

Chicago Midway

Mon 12/8

12:50 pm-11:33 pm

2 stops9h 43m

$239

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 1/22

6:00 am-6:36 pm

2 stops13h 36m

Chicago Midway

Sat 1/24

6:00 am-4:23 pm

2 stops9h 23m

$239

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 11/24

12:10 pm-4:39 pm

1 stop5h 29m

Chicago Midway

Tue 12/2

6:40 pm-11:38 pm

1 stop3h 58m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/3

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Wed 3/4

9:34 am-4:22 pm

1 stop5h 48m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 12/5

11:59 am-10:12 pm

1 stop11h 13m

Chicago Midway

Sun 12/7

6:37 pm-1:12 pm

1 stop17h 35m

$252

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 12/16

6:40 am-12:55 pm

1 stop7h 15m

Chicago Midway

Wed 12/24

6:00 pm-8:50 pm

Nonstop1h 50m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 52 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 6h 18m. 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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