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$103+ 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 5 — Dec 121
Fri 12/5
Fri 12/12
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 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$219
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$377
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. 3% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 15mFrontier
Thu 12/47:23 pmMDW - BDL
1 stop14h 45mFrontier
Deal found 11/2$219
This Southwest deal was found by Cheapflights users on 11/2. 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 12/711:55 amMDW - BDL
Nonstop2h 00mSouthwest
Deal found 11/2$225
This Southwest deal was found by Cheapflights users on 11/4. 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 12/47:25 amBDL - MDW
1 stop7h 20mSouthwest
Fri 12/51:45 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 11/4$226
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Sun 11/161:36 pmBDL - MDW
2 stops30h 03mFrontier
Wed 11/191:56 pmMDW - BDL
1 stop18h 56mFrontier
Deal found 11/3$227
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/1211:59 amBDL - MDW
1 stop8h 43mMultiple Airlines
Mon 12/158:42 pmMDW - BDL
2 stops41h 07mMultiple Airlines
Deal found 11/4$228
This Delta deal was found by Cheapflights users on 11/4. 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 11/189:43 amBDL - MDW
1 stop3h 51mDelta
Mon 11/246:48 pmMDW - BDL
1 stop3h 34mDelta
Deal found 11/4$232
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/121:30 pmBDL - MDW
2 stops10h 09mMultiple Airlines
Sun 12/146:37 pmMDW - BDL
1 stop17h 35mMultiple Airlines
Deal found 11/4$235
This Delta deal was found by Cheapflights users on 11/4. 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 12/115:23 amBDL - MDW
1 stop4h 31mDelta
Mon 12/156:40 pmMDW - BDL
1 stop3h 58mDelta
Deal found 11/4$236
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/211:30 pmBDL - MDW
2 stops10h 59mMultiple Airlines
Sat 11/225:57 pmMDW - BDL
1 stop18h 32mMultiple Airlines
Deal found 11/4$238
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 11/173:07 pmBDL - MDW
2 stops21h 31mFrontier
Wed 11/191:56 pmMDW - BDL
1 stop18h 56mFrontier
Deal found 11/3$240
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 stop8h 43mMultiple Airlines
Fri 12/128:42 pmMDW - BDL
2 stops49h 52mMultiple Airlines
Deal found 11/5$244
This Delta deal was found by Cheapflights users on 11/3. 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 12/57:05 amBTV - MDW
2 stops12h 13mDelta
Mon 12/86:40 pmMDW - BTV
1 stop3h 52mDelta
Deal found 11/3$254

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 5, 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

Sat 12/6

5:15 pm-6:45 pm

Nonstop2h 30m

Chicago Midway

Sun 12/7

11:55 am-2:55 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 11/18

9:43 am-12:34 pm

1 stop3h 51m

Chicago Midway

Mon 11/24

6:48 pm-11:22 pm

1 stop3h 34m

$232

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 2/14

2:00 pm-6:50 pm

1 stop5h 50m

Chicago Midway

Tue 2/17

9:55 am-1:00 pm

Nonstop2h 05m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 12/12

5:23 am-8:54 am

1 stop4h 31m

Chicago Midway

Sun 12/14

6:40 pm-11:38 pm

1 stop3h 58m

$236

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/11

5:23 am-8:54 am

1 stop4h 31m

Chicago Midway

Mon 12/15

6:40 pm-11:38 pm

1 stop3h 58m

$236

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

Tue 3/3

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Wed 3/4

6:00 am-1:42 pm

1 stop6h 42m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 11/24

6:00 am-11:52 am

1 stop6h 52m

Chicago Midway

Wed 12/3

5:29 pm-11:47 pm

1 stop5h 18m

$245

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 3/26

7:10 am-12:35 pm

1 stop6h 25m

Chicago Midway

Sun 3/29

5:59 pm-11:07 pm

1 stop4h 08m

$249

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 12/5

7:05 am-6:18 pm

2 stops12h 13m

Chicago Midway

Mon 12/8

6:40 pm-11:32 pm

1 stop3h 52m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 54 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 30m. The time it takes to get you to your destination can typically vary by up to 1h 21m. 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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