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$66+ Cheap flights from Midway (MDW) to Vermont

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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BTV
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
1 adult, Economy
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Cheap flight deals from Midway to Vermont

Cheapest flights from Midway to Vermont
Explore the most affordable flight options available from Midway to Vermont. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 30, 2025.

This Delta deal was found by Cheapflights users on 12/29. 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 12/296:08 pmMDW - BTV
1 stop4h 24mDelta
Sat 1/35:40 amBTV - MDW
1 stop4h 09mDelta
Deal found 12/29$559
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 12/296:15 amMDW - BDL
1 stop8h 14mMultiple Airlines
Thu 1/12:01 pmBDL - MDW
2 stops8h 57mMultiple Airlines
Deal found 12/28$740
This Southwest deal was found by Cheapflights users on 12/28. 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 12/3010:00 amMDW - ALB
Nonstop2h 00mSouthwest
Sat 1/38:30 pmALB - MDW
Nonstop2h 15mSouthwest
Deal found 12/28$757
This Southwest deal was found by Cheapflights users on 12/28. 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.
Mon 12/2910:00 amMDW - ALB
Nonstop2h 00mSouthwest
Fri 1/28:15 pmALB - MDW
Nonstop2h 15mSouthwest
Deal found 12/28$796
This Southwest deal was found by Cheapflights users on 12/28. 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 12/3010:00 amMDW - ALB
Nonstop2h 00mSouthwest
Thu 1/12:15 pmALB - MDW
1 stop4h 35mSouthwest
Deal found 12/28$847
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 12/296:15 amMDW - BDL
1 stop8h 14mFrontier
Thu 1/112:05 pmBDL - MDW
1 stop6h 33mFrontier
Deal found 12/28$879
This Southwest deal was found by Cheapflights users on 12/29. 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.
Mon 12/299:50 amMDW - BDL
Nonstop2h 05mSouthwest
Thu 1/15:15 amBDL - MDW
Nonstop2h 30mSouthwest
Deal found 12/29$958
This Southwest deal was found by Cheapflights users on 12/29. 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 12/309:50 amMDW - BDL
Nonstop2h 05mSouthwest
Sun 1/48:00 pmBDL - MDW
Nonstop2h 30mSouthwest
Deal found 12/29$1,007
This Delta deal was found by Cheapflights users on 12/28. 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.
Sun 12/286:08 pmMDW - BTV
1 stop4h 24mDelta
Tue 12/305:30 amBTV - MDW
1 stop7h 28mDelta
Deal found 12/28$2,115

Find flight deals from Midway to Vermont

Keep the following information in mind while searching for Midway to Vermont flight deals. Data was last updated December 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Kiwi.com)

One-way from

$66
(Southwest)

Popular in

December

Cheapest in

February

Average price

$538
Provider with most accurate pricing for Chicago (CHI)-Burlington flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Burlington flights.
Search Deals
From Chicago Midway to Vermont
Search Deals
One-way flight from Chicago Midway to Vermont
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 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 Midway to Vermont 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 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Vermont that are best for you.

Fly from

Midway

Fly to

Vermont

Route

Depart

Return

Price

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/17

9:50 am-3:55 pm

1 stop5h 05m

Hartford Bradley Intl

Sun 1/18

5:30 am-7:05 am

Nonstop2h 35m

$227

ChicagoBurlington

MDW - BTV

MDWBTV

Chicago Midway

Sat 2/14

11:45 am-11:18 pm

2 stops10h 33m

Burlington

Tue 2/17

6:00 am-12:46 pm

2 stops7h 46m

$259

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Mon 3/2

1:25 pm-4:15 pm

Nonstop1h 50m

Albany Intl

Wed 3/4

5:30 am-6:55 am

Nonstop2h 25m

$279

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/17

6:45 am-1:33 pm

1 stop5h 48m

Hartford Bradley Intl

Mon 1/19

6:03 am-1:09 pm

1 stop8h 06m

$279

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 1/27

1:25 pm-4:20 pm

Nonstop1h 55m

Hartford Bradley Intl

Tue 2/3

5:30 am-7:05 am

Nonstop2h 35m

$293

ChicagoBurlington

MDW - BTV

MDWBTV

Chicago Midway

Thu 1/8

9:32 am-4:09 pm

1 stop5h 37m

Burlington

Sat 1/10

7:10 am-12:48 pm

1 stop6h 38m

$304

ChicagoBurlington

MDW - BTV

MDWBTV

Chicago Midway

Fri 1/9

1:28 pm-11:10 pm

2 stops8h 42m

Burlington

Wed 1/14

5:22 am-10:27 am

1 stop6h 05m

$309

ChicagoBurlington

MDW - BTV

MDWBTV

Chicago Midway

Sat 3/14

1:10 pm-10:49 pm

2 stops8h 39m

Burlington

Thu 3/19

6:02 am-4:55 pm

2 stops11h 53m

$314

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Sat 3/14

6:45 pm-9:35 pm

Nonstop1h 50m

Albany Intl

Wed 3/18

6:15 pm-7:35 pm

Nonstop2h 20m

$316

ChicagoAlbany

MDW - ALB

MDWALB

Chicago Midway

Fri 1/23

1:25 pm-4:15 pm

Nonstop1h 50m

Albany Intl

Mon 1/26

5:30 am-6:55 am

Nonstop2h 25m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 48 results
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Best time to book a flight from Midway to Vermont

Have a flexible travel schedule? Discover the best time to fly to Vermont from Midway 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 Chicago Midway Airport to Vermont
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 Midway to Vermont. 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 Chicago Midway Airport to Vermont?

    There are many flights that can get you from Chicago Midway Airport to Vermont in 5h 05m. Fly via Southwest or Delta to get the fastest option. The distance from Chicago Midway Airport to Vermont is about 773 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago Midway Airport to Vermont?

    While some choose either Chicago Midway - Burlington or Chicago Midway - Albany Intl, Chicago Midway - Hartford Bradley Intl is the most popular route from Chicago Midway Airport to Vermont.

  • Can I find deals for flights from Midway to Vermont that include hotel bookings?

    Yes. In addition to deals on Midway to Vermont flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Vermont?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Vermont.

  • Can I find deals for business class flights from Midway to Vermont?

    Yes. Cheapflights offers flight deals from Midway to Vermont 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

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Alternative routes for Midway to Vermont

See prices for flight routes from nearby airports that may be better suited for you.
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