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$104+ Cheap flights from Vermont to Chicago (CHI)

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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Vermont to Chicago

Keep the following information in mind while searching for Vermont to Chicago flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Kiwi.com)

One-way from

$104
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$377

Good round-trip deal

$332 or less

Good one-way deal

$342 or less
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 (CHI)
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One-way flight from Vermont to Chicago (CHI)
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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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Price to beat on a round-trip flight from Vermont to Chicago (CHI).
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Price to beat on a one-way flight from Vermont to Chicago (CHI).
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Find flight deals from Vermont to Chicago

Cheapest flights from Vermont to Chicago
Explore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 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.
Fri 12/121:30 pmBDL - MDW
2 stops10h 09mMultiple Airlines
Sun 12/146:37 pmMDW - BDL
1 stop17h 35mMultiple Airlines
Deal found 11/2$217
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.
Wed 11/198:05 amBDL - ORD
1 stop16h 01mMultiple Airlines
Mon 11/246:15 pmORD - BDL
1 stop24h 17mMultiple Airlines
Deal found 11/2$218
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 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.
Fri 11/211:30 pmBDL - ORD
2 stops10h 36mMultiple Airlines
Mon 11/246:15 pmORD - BDL
1 stop24h 17mMultiple Airlines
Deal found 11/2$219
This Kiwi.com deal was found by Cheapflights users on 11/1. 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
1 stop19h 56mFrontier
Tue 11/256:15 pmMDW - BDL
2 stops48h 17mFrontier
Deal found 11/1$220
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.
Fri 12/121:35 pmBDL - ORD
2 stops8h 07mMultiple Airlines
Sun 12/146:00 amORD - BDL
1 stop16h 34mMultiple Airlines
Deal found 11/2$220
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/147:36 pmBDL - MDW
1 stop26h 46mFrontier
Wed 11/191:56 pmMDW - BDL
2 stops27h 21mFrontier
Deal found 11/1$221
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.
Thu 11/208:27 pmBDL - ORD
1 stop11h 59mMultiple Airlines
Wed 11/2610:47 amORD - BDL
2 stops10h 55mMultiple Airlines
Deal found 11/2$222
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 - ORD
2 stops24h 24mMultiple Airlines
Fri 11/216:48 amORD - BDL
1 stop9h 29mMultiple Airlines
Deal found 11/1$224
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.
Wed 11/268:00 pmBDL - MDW
Nonstop2h 30mSouthwest
Thu 11/272:00 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 11/2$225
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/176:00 amBDL - ORD
Nonstop3h 07mAmerican Airlines
Sun 1/185:35 pmORD - BDL
Nonstop2h 16mAmerican Airlines
Deal found 11/1$225
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.
Sun 11/167:39 pmBDL - ORD
1 stop15h 08mMultiple Airlines
Wed 11/196:05 pmORD - BDL
2 stops24h 27mMultiple Airlines
Deal found 11/2$226

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vermont to Chicago 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 3, 2025.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.

Fly from

Vermont

Fly to

Chicago

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 - ORD

BDLORD

Hartford Bradley Intl

Sat 1/10

4:46 pm-6:36 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 1/11

11:04 am-2:22 pm

Nonstop2h 18m

$227

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 1/10

4:46 pm-6:36 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 1/12

11:04 am-2:22 pm

Nonstop2h 18m

$227

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 1/22

7:10 am-12:48 pm

1 stop6h 38m

Chicago Midway

Sat 1/24

11:45 am-10:48 pm

2 stops10h 03m

$234

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Fri 12/5

7:05 am-4:57 pm

2 stops10h 52m

Chicago O'Hare Intl

Mon 12/8

6:00 am-1:41 pm

1 stop6h 41m

$234

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 11/26

8:00 pm-9:30 pm

Nonstop2h 30m

Chicago Midway

Thu 11/27

11:50 am-4:30 pm

1 stop3h 40m

$235

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

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Mon 11/24

6:00 am-10:01 am

1 stop5h 01m

Chicago O'Hare Intl

Thu 11/27

9:42 am-5:21 pm

1 stop6h 39m

$251

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Sun 1/18

10:30 am-12:23 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 1/19

8:52 pm-11:57 pm

Nonstop2h 05m

$252

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 11/2

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

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

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

Currently, September is the cheapest month in which you can book a flight from Vermont to Chicago (average of $201). Flying from Vermont to Chicago in April is currently the most expensive (average of $329). 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 VT to CHI?

Find hourly flight availability from Vermont to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

One of the essential ways to save on airfare from Vermont to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 41% on airfare.

Weekly flight availability from Vermont to Chicago

Explore weekly flight availability from Vermont to Chicago. 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 November 3, 2025.

The most flights from USVT to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

Related info for your journey

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

    Departing from Vermont to Chicago will take you 2h 30m. The distance between Vermont and Chicago is about 773 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $104. Users have also found prices from $114 and $126 on United Airlines and Delta, respectively.

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

    Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Albany Intl - Chicago O'Hare Intl or Hartford Bradley Intl - Chicago Midway when deciding on the best route from Vermont to Chicago.

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

    No one likes to see their flight delayed. When booking a flight from Vermont to Chicago consider choosing Air Canada (79%), United Airlines (79%) or Air New Zealand (79%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Vermont to Chicago?

    Looking at all options, your cheapest flight can be booked for $154. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $157 on average, our data indicates $1,009 when flying from Vermont to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Vermont to Chicago 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 Vermont to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Vermont to Chicago (average of $201). Flying from Vermont to Chicago in April is currently the most expensive (average of $329). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Vermont to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Vermont to Chicago

Discover the top 2 airlines that operate flights from Vermont to Chicago. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$308FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$232Average$368FlexibilityNo cancel feeOn-time69%

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