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$100+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Nov 16 — Nov 231
Sun 11/16
Sun 11/23
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 October 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$338
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. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:36 pmBDL - MDW
1 stop26h 46mMultiple Airlines
Mon 11/39:32 amMDW - BDL
2 stops12h 06mMultiple Airlines
Deal found 10/16$207
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Fri 10/316:36 pmBDL - MDW
2 stops16h 50mMultiple Airlines
Sun 11/210:12 amMDW - BDL
1 stop25h 29mMultiple Airlines
Deal found 10/15$209
This Booking.com deal was found by Cheapflights users on 10/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:36 pmBDL - MDW
1 stop21h 50mFrontier
Sun 11/210:12 amMDW - BDL
1 stop25h 29mFrontier
Deal found 10/14$212
This Southwest deal was found by Cheapflights users on 10/15. 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.
Sat 12/65:15 pmBDL - MDW
Nonstop2h 30mSouthwest
Sun 12/77:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 10/15$215
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/303:00 pmBDL - MDW
2 stops24h 22mMultiple Airlines
Sun 11/26:06 pmMDW - BDL
1 stop17h 39mMultiple Airlines
Deal found 10/15$216
This Trip.com deal was found by Cheapflights users on 10/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:39 amBDL - MDW
1 stop23h 42mFrontier
Sun 10/2611:57 amMDW - BDL
1 stop21h 49mFrontier
Deal found 10/14$217
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Sat 11/111:13 amBDL - MDW
1 stop8h 26mMultiple Airlines
Mon 11/39:32 amMDW - BDL
2 stops12h 06mMultiple Airlines
Deal found 10/13$227
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:00 amBTV - MDW
1 stop6h 55mDelta
Mon 12/156:40 pmMDW - BTV
1 stop3h 52mDelta
Deal found 10/15$229
This Southwest deal was found by Cheapflights users on 10/14. 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.
Thu 11/132:00 pmBDL - MDW
1 stop7h 40mSouthwest
Sat 11/155:45 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 10/14$231
This Delta deal was found by Cheapflights users on 10/14. 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.
Fri 12/52:21 pmBTV - MDW
2 stops10h 28mDelta
Mon 12/86:40 pmMDW - BTV
1 stop3h 52mDelta
Deal found 10/14$234
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:45 amBTV - MDW
2 stops7h 49mDelta
Mon 12/1512:50 pmMDW - BTV
2 stops9h 43mDelta
Deal found 10/15$239
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:14 amBTV - MDW
1 stop6h 14mDelta
Sat 11/111:10 amMDW - BTV
1 stop4h 25mDelta
Deal found 10/15$249

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 October 17, 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

Tue 12/9

5:45 am-12:34 pm

2 stops7h 49m

Chicago Midway

Mon 12/15

6:40 pm-11:32 pm

1 stop3h 52m

$234

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/17

7:30 am-11:55 am

1 stop5h 25m

Chicago Midway

Wed 12/24

3:29 pm-11:49 pm

1 stop7h 20m

$235

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 12/10

5:45 am-12:34 pm

2 stops7h 49m

Chicago Midway

Mon 12/15

12:50 pm-11:33 pm

2 stops9h 43m

$239

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 12/5

2:21 pm-11:49 pm

2 stops10h 28m

Chicago Midway

Mon 12/8

12:50 pm-11:22 pm

2 stops9h 32m

$239

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 10/29

7:14 am-12:28 pm

1 stop6h 14m

Chicago Midway

Sat 11/1

11:10 am-4:35 pm

1 stop4h 25m

$249

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 12/5

12:10 pm-5:35 pm

2 stops6h 25m

Chicago Midway

Sun 12/7

11:55 am-2:55 pm

Nonstop2h 00m

$255

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 11/9

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Sun 11/9

6:48 pm-11:22 pm

1 stop3h 34m

$258

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 11/24

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Tue 12/2

6:40 pm-11:38 pm

1 stop3h 58m

$262

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/18

5:23 am-8:54 am

1 stop4h 31m

Chicago Midway

Thu 12/25

6:08 pm-11:14 pm

1 stop4h 06m

$262

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/25

5:30 am-8:49 am

1 stop4h 19m

Chicago Midway

Tue 12/30

6:08 pm-11:14 pm

1 stop4h 06m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 58 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 Delta and Southwest fly from Vermont to Chicago Midway Airport in about 6h 25m. The time it takes to get you to your destination can typically vary by up to 1h 24m. 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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