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$79+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Mai 12 — Mai 191
Di 5/12
Di 5/19
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 April 12, 2026.

This American Airlines deal was found by Cheapflights users on 4/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 6/306:33 am
BTV
-
ORD
Nonstop2h 57m
American Airlines
Fr 7/33:48 pm
ORD
-
BTV
Nonstop2h 29m
American Airlines
Deal found 4/8$269
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/512:13 pm
ALB
-
ORD
2 stops11h 01m
Multiple Airlines
Do 5/147:33 pm
ORD
-
ALB
1 stop13h 29m
Multiple Airlines
Deal found 4/8$285
This Southwest deal was found by Cheapflights users on 4/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 5/66:40 pm
ALB
-
MDW
Nonstop2h 10m
Southwest
Mi 5/1312:45 pm
MDW
-
ALB
Nonstop1h 55m
Southwest
Deal found 4/8$285
This United Airlines deal was found by Cheapflights users on 4/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 5/66:00 am
ALB
-
ORD
Nonstop2h 34m
United Airlines
Sa 5/99:38 pm
ORD
-
ALB
Nonstop2h 10m
United Airlines
Deal found 4/9$287
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 7/107:53 pm
ALB
-
ORD
1 stop28h 15m
Multiple Airlines
Do 7/165:26 pm
ORD
-
ALB
1 stop24h 37m
Multiple Airlines
Deal found 4/11$288
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/95:30 am
BTV
-
MDW
1 stop5h 29m
Delta
Di 5/125:10 pm
MDW
-
BTV
1 stop5h 34m
Delta
Deal found 4/9$289
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Do 6/117:19 pm
BTV
-
ORD
1 stop5h 40m
American Airlines
Sa 6/131:19 pm
ORD
-
BTV
1 stop8h 24m
American Airlines
Deal found 4/7$289
This Kiwi.com deal was found by Cheapflights users on 4/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 5/410:52 am
ALB
-
ORD
1 stop14h 03m
Multiple Airlines
Mi 5/133:55 pm
ORD
-
ALB
2 stops18h 35m
Multiple Airlines
Deal found 4/8$291
This Delta deal was found by Cheapflights users on 4/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/27:10 am
BTV
-
MDW
1 stop6h 33m
Delta
Di 5/55:21 pm
MDW
-
BTV
1 stop5h 38m
Delta
Deal found 4/8$291
This United Airlines deal was found by Cheapflights users on 4/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/145:30 am
BTV
-
ORD
1 stop6h 56m
United Airlines
Mo 5/186:10 pm
ORD
-
BTV
Nonstop2h 16m
United Airlines
Deal found 4/9$291
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Fr 4/2410:52 am
ALB
-
ORD
2 stops13h 15m
Multiple Airlines
So 4/261:22 pm
ORD
-
ALB
1 stop19h 40m
Multiple Airlines
Deal found 4/9$294
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/71:10 pm
BTV
-
ORD
1 stop6h 59m
Delta
Mo 5/112:00 pm
ORD
-
BTV
2 stops8h 44m
Delta
Deal found 4/9$294

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 April 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(American Airlines)

One-way from

$79
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$371

Good round-trip deal

$366 or less

Good one-way deal

$277 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. 6% potential increase in price ($25 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 April 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 April 12, 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

Di 5/12

5:00 pm-6:42 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sa 5/16

6:10 pm-9:26 pm

Nonstop2h 16m

$269

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Mi 5/6

7:19 pm-11:37 pm

1 stop5h 18m

Chicago O'Hare Intl

Sa 5/9

11:05 am-2:22 pm

Nonstop2h 17m

$279

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Mi 5/6

5:40 am-12:07 pm

1 stop7h 27m

Chicago Midway

Sa 5/9

5:29 pm-11:44 pm

1 stop5h 15m

$289

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Do 8/20

12:45 pm-2:29 pm

Nonstop2h 44m

Chicago O'Hare Intl

So 8/23

7:45 am-11:18 am

Nonstop2h 33m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Di 5/12

7:29 am-12:42 pm

1 stop6h 13m

Chicago Midway

Sa 5/16

6:36 pm-11:02 pm

1 stop3h 26m

$291

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sa 5/9

10:45 am-4:45 pm

1 stop7h 00m

Chicago O'Hare Intl

Di 5/12

11:26 am-11:02 pm

2 stops10h 36m

$294

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Mi 5/20

6:00 am-1:01 pm

2 stops8h 01m

Chicago O'Hare Intl

Mo 5/25

5:30 am-11:57 am

1 stop5h 27m

$294

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Mi 5/27

7:29 am-12:42 pm

1 stop6h 13m

Chicago Midway

Fr 6/12

5:11 pm-11:54 pm

1 stop5h 43m

$299

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Do 5/28

7:29 am-12:42 pm

1 stop6h 13m

Chicago Midway

Do 6/11

5:11 pm-11:54 pm

1 stop5h 43m

$299

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Mi 5/6

2:05 pm-11:58 pm

2 stops10h 53m

Chicago O'Hare Intl

Sa 5/9

11:09 am-8:42 pm

2 stops8h 33m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

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, 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 March is currently the most expensive (average of $281). 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 April 12, 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 27% 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 April 12, 2026.

The most flights from USVT to CHI are scheduled on a Tuesday (12 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (9 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 2h 10m. The distance between Vermont and Chicago is about 715 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 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 Republic Airways (71%), Air Canada (71%) or Air New Zealand (71%) 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 $179. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $200 on average, our data indicates $578 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 March is currently the most expensive (average of $281). 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
Lansing
Merrillville
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 April 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$309FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$352FlexibilityNo cancel feeOn-time69%

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