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$101+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Nov 14 — Nov 211
Fri 11/14
Fri 11/21
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 October 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$202
(American Airlines)

One-way from

$101
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$338

Good round-trip deal

$327 or less

Good one-way deal

$338 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. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 15, 2025.

This American Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 10/307:10 amBDL - ORD
Nonstop2h 42mAmerican Airlines
Fri 10/315:42 pmORD - BDL
Nonstop2h 14mAmerican Airlines
Deal found 10/14$202
This United Airlines deal was found by Cheapflights users on 10/13. 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 11/66:10 amBDL - ORD
Nonstop2h 52mUnited Airlines
Sun 11/98:58 amORD - BDL
Nonstop2h 17mUnited Airlines
Deal found 10/13$205
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/128:05 amBDL - ORD
1 stop16h 01mMultiple Airlines
Wed 11/1912:37 pmORD - BDL
2 stops28h 40mMultiple Airlines
Deal found 10/13$211
This Booking.com deal was found by Cheapflights users on 10/14. 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.
Fri 10/311:36 pmBDL - MDW
1 stop21h 50mFrontier
Sun 11/210:12 amMDW - BDL
1 stop25h 29mFrontier
Deal found 10/14$212
This United Airlines deal was found by Cheapflights users on 10/14. 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 10/3110:34 amBDL - ORD
1 stop7h 19mUnited Airlines
Sun 11/26:20 pmORD - BDL
Nonstop2h 18mUnited Airlines
Deal found 10/14$212
This United Airlines deal was found by Cheapflights users on 10/13. 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 11/136:10 amBDL - ORD
Nonstop2h 52mUnited Airlines
Sun 11/168:58 amORD - BDL
Nonstop2h 17mUnited Airlines
Deal found 10/13$214
This Southwest deal was found by Cheapflights users on 10/15. 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 12/77:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 10/15$215
This American Airlines deal was found by Cheapflights users on 10/14. 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 12/176:07 amBDL - ORD
Nonstop3h 07mAmerican Airlines
Sun 1/181:03 pmORD - BDL
Nonstop2h 17mAmerican Airlines
Deal found 10/14$215
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/303:00 pmBDL - MDW
2 stops24h 22mMultiple Airlines
Sun 11/26:06 pmMDW - BDL
1 stop17h 39mMultiple Airlines
Deal found 10/15$216
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 12/58:39 pmBDL - ORD
1 stop18h 37mMultiple Airlines
Sun 12/74:16 pmORD - BDL
1 stop24h 10mMultiple Airlines
Deal found 10/14$216
This Trip.com deal was found by Cheapflights users on 10/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:39 amBDL - MDW
1 stop23h 42mFrontier
Sun 10/2611:57 amMDW - BDL
1 stop21h 49mFrontier
Deal found 10/14$217
This Mytrip deal was found by Cheapflights users on 10/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:13 amBDL - MDW
1 stop11h 22mFrontier
Sun 11/910:12 amMDW - BDL
1 stop25h 29mFrontier
Deal found 10/15$218

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 October 15, 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 11/8

11:13 am-9:35 pm

1 stop11h 22m

Chicago Midway

Sun 11/9

10:12 am-12:41 pm

1 stop25h 29m

$218

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 1/13

10:07 am-2:25 pm

1 stop5h 18m

Chicago O'Hare Intl

Fri 2/6

11:04 am-2:22 pm

Nonstop2h 18m

$225

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 1/13

4:46 pm-6:36 pm

Nonstop2h 50m

Chicago O'Hare Intl

Tue 2/3

11:04 am-2:22 pm

Nonstop2h 18m

$227

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 1/17

5:00 pm-8:38 pm

1 stop4h 38m

Chicago O'Hare Intl

Sat 5/9

8:55 am-4:16 pm

1 stop6h 21m

$229

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Wed 12/10

4:55 pm-8:35 pm

1 stop4h 40m

Chicago O'Hare Intl

Mon 12/15

7:00 am-3:14 pm

1 stop7h 14m

$229

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 11/6

7:23 pm-11:43 pm

1 stop5h 20m

Chicago O'Hare Intl

Sat 11/8

7:15 am-1:34 pm

1 stop5h 19m

$229

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Wed 12/3

6:50 am-12:43 pm

1 stop6h 53m

Chicago O'Hare Intl

Mon 12/15

5:50 pm-11:22 pm

1 stop4h 32m

$229

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Wed 10/29

4:46 pm-6:32 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sat 11/1

11:20 am-2:28 pm

Nonstop2h 08m

$229

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Tue 12/2

3:54 pm-9:39 pm

1 stop6h 45m

Chicago O'Hare Intl

Tue 12/9

5:50 pm-11:22 pm

1 stop4h 32m

$229

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 10/31

3:30 pm-9:19 pm

1 stop6h 49m

Chicago O'Hare Intl

Sun 11/2

5:20 am-11:40 am

1 stop5h 20m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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 October 15, 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 36% 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 October 15, 2025.

The most flights from USVT to CHI are scheduled on a Tuesday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

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

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 4h 38m. The distance between Vermont and Chicago is about 761 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 United Airlines. According to our data, you can fly for as low as $104. Users have also found prices from $104 and $115 on Southwest and Delta, respectively.

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

    Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Hartford Bradley Intl - Chicago Midway or Albany Intl - Chicago O'Hare Intl 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 Qatar Airways (90%), Air Canada (84%) or Air New Zealand (84%) 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 $140. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $157 on average, our data indicates $733 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
Chesterton

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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 October 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$308FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$365FlexibilityNo cancel feeOn-time69%

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