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$123+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
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Cheap 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 May 21, 2026.

This American Airlines deal was found by Cheapflights users on 5/20. 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.
Fri 6/197:47 pm
BTV
-
ORD
Nonstop2h 53m
American Airlines
Sun 6/218:35 pm
ORD
-
BTV
Nonstop2h 23m
American Airlines
Deal found 5/20$269
This American Airlines deal was found by Cheapflights users on 5/17. 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 7/17:47 pm
BTV
-
ORD
Nonstop2h 53m
American Airlines
Wed 7/810:45 am
ORD
-
BTV
1 stop4h 59m
American Airlines
Deal found 5/17$278
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Fri 6/196:20 pm
BTV
-
ORD
1 stop7h 14m
American Airlines
Mon 6/228:35 pm
ORD
-
BTV
Nonstop2h 23m
American Airlines
Deal found 5/20$279
This Delta deal was found by Cheapflights users on 5/19. 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.
Thu 6/111:20 pm
BTV
-
MDW
1 stop6h 11m
Delta
Sun 6/149:17 am
MDW
-
BTV
1 stop5h 54m
Delta
Deal found 5/19$289
This Delta deal was found by Cheapflights users on 5/19. 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.
Sat 9/197:30 am
BTV
-
MDW
2 stops8h 57m
Delta
Sat 9/264:30 pm
MDW
-
BTV
1 stop6h 18m
Delta
Deal found 5/19$294
This Delta deal was found by Cheapflights users on 5/21. 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 8/512:09 pm
BTV
-
ORD
1 stop6h 54m
Delta
Sat 8/88:02 am
ORD
-
BTV
2 stops11h 56m
Delta
Deal found 5/21$294
This American Airlines deal was found by Cheapflights users on 5/17. 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 6/47:19 pm
BTV
-
ORD
1 stop5h 39m
American Airlines
Sun 6/78:35 pm
ORD
-
BTV
Nonstop2h 23m
American Airlines
Deal found 5/17$299
This United Airlines deal was found by Cheapflights users on 5/20. 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 6/276:00 am
BTV
-
ORD
Nonstop2h 44m
United Airlines
Sun 6/286:10 pm
ORD
-
BTV
Nonstop2h 19m
United Airlines
Deal found 5/20$302
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 8/145:20 am
BTV
-
ORD
Nonstop2h 55m
American Airlines
Sun 8/167:04 pm
ORD
-
BTV
Nonstop2h 26m
American Airlines
Deal found 5/19$308
This Delta deal was found by Cheapflights users on 5/20. 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.
Sat 6/62:33 pm
BTV
-
MDW
1 stop7h 36m
Delta
Fri 6/195:11 pm
MDW
-
BTV
1 stop5h 48m
Delta
Deal found 5/20$309
This American Airlines deal was found by Cheapflights users on 5/19. 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 6/36:30 am
BTV
-
ORD
Nonstop2h 57m
American Airlines
Sat 6/68:46 pm
ORD
-
BTV
Nonstop2h 23m
American Airlines
Deal found 5/19$310
This Delta deal was found by Cheapflights users on 5/20. 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.
Sat 6/68:00 am
BTV
-
ORD
2 stops9h 51m
Delta
Fri 6/196:00 pm
ORD
-
BTV
1 stop5h 14m
Delta
Deal found 5/20$314

Find flight deals from Vermont to Chicago

Keep the following information in mind while searching for Vermont to Chicago flight deals. Data was last updated May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$123
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$294

Good round-trip deal

$394 or less

Good one-way deal

$223 or less
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 (CHI)
Search Deals
One-way flight from Vermont to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Vermont to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Vermont to Chicago (CHI).
Search Deals

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 May 21, 2026.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 9/19

4:47 pm-6:31 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 9/26

7:45 am-11:15 am

Nonstop2h 30m

$269

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Wed 6/17

9:48 am-11:30 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 6/24

6:25 pm-9:45 pm

Nonstop2h 20m

$269

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 6/11

1:20 pm-6:31 pm

1 stop6h 11m

Chicago Midway

Sun 6/14

9:17 am-4:11 pm

1 stop5h 54m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 8/7

5:14 am-11:51 am

1 stop7h 37m

Chicago Midway

Mon 8/10

5:10 pm-11:57 pm

1 stop5h 47m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 9/18

6:00 am-11:54 am

1 stop6h 54m

Chicago Midway

Sat 9/26

5:59 pm-11:02 pm

1 stop4h 03m

$289

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 7/2

7:19 am-1:00 pm

1 stop6h 41m

Chicago O'Hare Intl

Sun 7/5

5:30 am-1:46 pm

1 stop7h 16m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Mon 8/10

6:59 am-12:39 pm

1 stop6h 40m

Chicago Midway

Wed 12/16

1:05 pm-11:56 pm

2 stops9h 51m

$294

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 6/11

1:20 pm-6:31 pm

1 stop6h 11m

Chicago Midway

Wed 6/17

12:50 pm-12:14 am

2 stops10h 24m

$294

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 10/21

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Sat 10/24

1:05 pm-11:56 pm

2 stops9h 51m

$294

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 8/13

6:00 am-4:15 pm

2 stops11h 15m

Chicago Midway

Sun 8/16

6:42 pm-11:25 pm

1 stop3h 43m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 60 resultsSorted by cheapest first
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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, November is the cheapest month in which you can book a flight from Vermont to Chicago (average of $99). Flying from Vermont to Chicago in January is currently the most expensive (average of $209). 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 May 21, 2026.

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 30% 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 May 21, 2026.

The most flights from USVT to CHI are scheduled on a Thursday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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

How far ahead should I book a flight from Vermont to Chicago?

Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Vermont to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 44m. 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 most popular routes from Vermont to Chicago?

    Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Albany Intl - Chicago O'Hare Intl or Burlington - 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 (79%), SkyWest Airlines (75%) or Air Canada (72%) 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 $173. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $244 on average, our data indicates $647 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, November is the cheapest month in which you can book a flight from Vermont to Chicago (average of $99). Flying from Vermont to Chicago in January is currently the most expensive (average of $209). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$321FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$358FlexibilityNo cancel feeOn-time69%

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