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Vermont

$66+ Cheap flights from Chicago (CHI) 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BTV
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Chicago to Vermont

Keep the following information in mind while searching for Chicago to Vermont flight deals. Data was last updated September 11, 2025.

Round-trip from

$178
(Southwest)

One-way from

$66
(Southwest)

Popular in

April

Cheapest in

July

Average price

$381

Good round-trip deal

$279 or less

Good one-way deal

$184 or less
From Chicago (CHI) to Vermont
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One-way flight from Chicago (CHI) to Vermont
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Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Vermont.
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Price to beat on a one-way flight from Chicago (CHI) to Vermont.
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Find flight deals from Chicago to Vermont

Cheapest flights from Chicago to Vermont
Explore the most affordable flight options available from Chicago to Vermont. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Booking.com deal was found by Cheapflights users on 9/8. 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.
Thu 9/258:49 pmORD - BDL
1 stop22h 08mFrontier
Sun 9/288:37 pmBDL - ORD
1 stop24h 07mFrontier
Deal found 9/8$177
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 9/188:49 pmORD - BDL
1 stop22h 08mFrontier
Sun 9/2112:18 pmBDL - ORD
1 stop12h 52mFrontier
Deal found 9/10$178
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:49 pmORD - BDL
1 stop22h 08mFrontier
Sun 10/58:37 pmBDL - ORD
1 stop24h 07mFrontier
Deal found 9/9$179
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 11/111:45 amMDW - BDL
1 stop6h 15mSouthwest
Sun 11/25:15 amBDL - MDW
Nonstop2h 30mSouthwest
Deal found 9/11$183
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/310:45 amORD - BDL
1 stop7h 07mUnited Airlines
Sat 10/410:33 amBDL - ORD
1 stop5h 01mUnited Airlines
Deal found 9/11$185
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/75:35 amMDW - BDL
1 stop6h 40mSouthwest
Sat 10/115:10 pmBDL - MDW
Nonstop2h 25mSouthwest
Deal found 9/9$185
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Wed 11/512:37 pmORD - BDL
1 stop20h 05mFrontier
Sun 11/910:59 amBDL - ORD
1 stop24h 42mFrontier
Deal found 9/10$186
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/199:48 amMDW - BDL
1 stop9h 09mFrontier
Sun 9/218:37 pmBDL - MDW
1 stop11h 46mFrontier
Deal found 9/10$186
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:20 pmORD - BDL
1 stop4h 13mUnited Airlines
Sun 11/25:10 amBDL - ORD
Nonstop2h 52mUnited Airlines
Deal found 9/11$187
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:32 amORD - BDL
Nonstop2h 19mUnited Airlines
Tue 10/146:38 pmBDL - ORD
Nonstop2h 43mUnited Airlines
Deal found 9/8$188
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:31 pmORD - BDL
Nonstop2h 25mAmerican Airlines
Sun 10/127:10 amBDL - ORD
Nonstop2h 42mAmerican Airlines
Deal found 9/9$190
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 10/166:07 pmORD - BDL
1 stop15h 37mFrontier
Mon 10/204:20 pmBDL - ORD
1 stop8h 19mFrontier
Deal found 9/10$193

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago to Vermont that are best for you.

Fly from

Chicago

Fly to

Vermont

Route

Depart

Return

Price

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 10/21

5:35 am-3:40 pm

1 stop9h 05m

Hartford Bradley Intl

Wed 10/22

5:30 am-6:55 am

Nonstop2h 25m

$178

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 10/25

12:50 pm-3:50 pm

Nonstop2h 00m

Hartford Bradley Intl

Tue 10/28

12:05 pm-7:10 pm

2 stops8h 05m

$180

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 11/1

11:45 am-7:00 pm

1 stop6h 15m

Hartford Bradley Intl

Sun 11/2

5:15 am-6:45 am

Nonstop2h 30m

$183

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 10/7

5:35 am-1:15 pm

1 stop6h 40m

Hartford Bradley Intl

Sat 10/11

5:10 pm-6:35 pm

Nonstop2h 25m

$185

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Tue 9/30

9:50 am-4:10 pm

1 stop5h 20m

Hartford Bradley Intl

Tue 10/7

6:00 am-12:16 pm

1 stop7h 16m

$197

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/3

9:10 am-4:13 pm

1 stop6h 03m

Hartford Bradley Intl

Sun 10/5

5:35 am-10:19 am

1 stop5h 44m

$197

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 9/30

6:00 am-1:31 pm

1 stop6h 31m

Hartford Bradley Intl

Tue 10/7

7:05 am-11:53 am

1 stop5h 48m

$197

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 10/11

6:23 pm-11:14 pm

1 stop3h 51m

Hartford Bradley Intl

Tue 10/14

5:30 am-8:40 am

1 stop4h 10m

$197

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/3

1:36 pm-10:29 pm

1 stop7h 53m

Hartford Bradley Intl

Sun 10/5

7:10 am-12:10 pm

1 stop6h 00m

$199

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Wed 10/15

7:32 am-10:51 am

Nonstop2h 19m

Hartford Bradley Intl

Mon 10/20

6:38 pm-8:21 pm

Nonstop2h 43m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Vermont

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

What is the cheapest month to book a flight from Chicago to Vermont?

Currently, January is the cheapest month in which you can book a flight from Chicago to Vermont (average of $327). Flying from Chicago to Vermont in December is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to VT?

Find hourly flight availability from Chicago to Vermont. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from Chicago to Vermont, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Vermont

Explore weekly flight availability from Chicago to Vermont. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from CHI to USVT are scheduled on a Monday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Chicago to Vermont?

Reviews of airlines servicing Vermont

Get insights into the airlines that provide service to Vermont. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Vermont. Reviews last updated September 11, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Chicago to Vermont have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Vermont?

    Airlines like Southwest, Delta, and JetBlue fly from Chicago to Vermont in about 5h 20m. The time it takes to get you to your destination can typically vary by up to 3h 45m. There are 780 mi between Chicago and Vermont. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Vermont one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $67. American Airlines flights start at $67 while deals on Southwest start at $67 one-way.

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

    The most popular flight routes from Chicago to Vermont are Chicago O'Hare Intl - Hartford Bradley Intl, Chicago O'Hare Intl - Burlington and Chicago O'Hare Intl - Albany Intl.

  • What are the most reliable airlines from Chicago to Vermont?

    The top 3 most reliable airlines when flying from Chicago to Vermont are United Airlines (77%), Air Canada (73%) and Air New Zealand (73%).

  • What are the cheapest flights from Chicago to Vermont?

    Looking at all options, your cheapest flight can be booked for $97. While the most popular route (Chicago O'Hare Intl - Hartford Bradley Intl) can be booked for $133 on average, our data indicates $314 when flying from Chicago to Vermont.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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.

  • What is the cheapest month to book a flight from Chicago to Vermont?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Vermont (average of $327). Flying from Chicago to Vermont in December is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Vermont

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Vermont

Discover the top 3 airlines that operate flights from Chicago to Vermont. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$210Average$329FlexibilityNo cancel feeOn-time71%
DeltaCheapest$228Average$298FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$255Average$384FlexibilityNo cancel feeOn-time69%

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