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$67+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — MDW
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheap 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 December 27, 2025.

This Delta deal was found by Cheapflights users on 12/25. 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 12/316:09 amBDL - MDW
1 stop5h 57mDelta
Fri 1/212:45 pmMDW - BDL
1 stop8h 03mDelta
Deal found 12/25$447
This Booking.com deal was found by Cheapflights users on 12/26. 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.
Sun 12/2812:05 pmBDL - MDW
1 stop11h 07mFrontier
Wed 12/313:10 pmMDW - BDL
1 stop27h 07mFrontier
Deal found 12/26$503
This Delta deal was found by Cheapflights users on 12/25. 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 12/296:07 amALB - MDW
1 stop6h 51mDelta
Thu 1/16:00 amMDW - ALB
1 stop6h 18mDelta
Deal found 12/25$585
This Delta deal was found by Cheapflights users on 12/25. 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 12/296:00 amBDL - MDW
1 stop6h 58mDelta
Thu 1/13:29 pmMDW - BDL
1 stop7h 07mDelta
Deal found 12/25$637
This Southwest deal was found by Cheapflights users on 12/26. 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 12/275:10 amALB - MDW
Nonstop2h 20mSouthwest
Fri 1/27:45 pmMDW - ALB
Nonstop1h 50mSouthwest
Deal found 12/26$673
This Southwest deal was found by Cheapflights users on 12/26. 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 12/285:00 amBDL - MDW
Nonstop2h 30mSouthwest
Sat 1/39:50 amMDW - BDL
Nonstop2h 05mSouthwest
Deal found 12/26$737
This Southwest deal was found by Cheapflights users on 12/25. 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 12/278:30 pmALB - MDW
Nonstop2h 15mSouthwest
Tue 12/3010:00 amMDW - ALB
Nonstop2h 00mSouthwest
Deal found 12/25$756
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 12/264:30 pmBDL - MDW
1 stop17h 49mFrontier
Sun 12/2810:50 pmMDW - BDL
2 stops43h 19mFrontier
Deal found 12/25$773
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/291:30 pmBDL - MDW
2 stops9h 28mMultiple Airlines
Wed 12/313:10 pmMDW - BDL
1 stop27h 07mMultiple Airlines
Deal found 12/26$795
This Southwest deal was found by Cheapflights users on 12/26. 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 12/288:00 pmBDL - MDW
Nonstop2h 30mSouthwest
Fri 1/27:55 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 12/26$803
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/291:30 pmBDL - MDW
2 stops9h 28mMultiple Airlines
Sat 1/36:12 amMDW - BDL
1 stop27h 58mMultiple Airlines
Deal found 12/26$811

Find flight deals from Vermont to Midway

Keep the following information in mind while searching for Vermont to Midway flight deals. Data was last updated December 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$162
(Frontier)

One-way from

$67
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$372
Provider with most accurate pricing for Burlington-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Burlington-Chicago (CHI) flights.
Search Deals
From Vermont to Chicago Midway
Search Deals
One-way flight from Vermont to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 27, 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

Sat 2/7

7:10 am-12:46 pm

1 stop6h 36m

Chicago Midway

Mon 2/9

6:35 pm-11:27 pm

1 stop3h 52m

$229

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 1/15

6:00 am-4:29 pm

2 stops11h 29m

Chicago Midway

Sun 1/18

6:14 pm-11:19 pm

1 stop4h 05m

$234

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 1/14

5:22 am-10:27 am

1 stop6h 05m

Chicago Midway

Sat 1/17

11:45 am-11:19 pm

2 stops10h 34m

$234

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 3/27

7:10 am-12:29 pm

1 stop6h 19m

Chicago Midway

Mon 3/30

6:34 pm-11:03 pm

1 stop3h 29m

$249

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 1/9

6:00 am-4:29 pm

2 stops11h 29m

Chicago Midway

Tue 1/13

6:14 pm-11:19 pm

1 stop4h 05m

$274

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sun 1/18

5:30 am-8:52 am

1 stop4h 22m

Chicago Midway

Mon 1/19

6:35 pm-11:26 pm

1 stop3h 51m

$276

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/17

5:30 am-8:52 am

1 stop4h 22m

Chicago Midway

Mon 1/26

10:46 am-5:05 pm

1 stop5h 19m

$276

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 1/15

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Mon 1/26

1:25 pm-4:15 pm

Nonstop1h 50m

$289

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/24

5:30 am-8:52 am

1 stop4h 22m

Chicago Midway

Mon 1/26

6:00 am-11:55 am

1 stop4h 55m

$299

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 1/17

3:35 pm-7:00 pm

1 stop4h 25m

Chicago Midway

Sun 1/18

7:50 am-3:00 pm

1 stop6h 10m

$301

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 46 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 2h 30m. The time it takes to get you to your destination can typically vary by up to 4h 08m. There are 715 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
Merrillville
Hammond
Porter
Benton Harbor

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