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$70+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Mar 26 — Apr 21
Thu 3/26
Thu 4/2
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 February 24, 2026.

This United Airlines deal was found by Cheapflights users on 2/22. 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.
Sun 5/36:00 am
BTV
-
ORD
Nonstop2h 38m
United Airlines
Sat 5/96:10 pm
ORD
-
BTV
Nonstop2h 16m
United Airlines
Deal found 2/22$209
This American Airlines deal was found by Cheapflights users on 2/23. 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 9/116:09 pm
BTV
-
ORD
Nonstop2h 41m
American Airlines
Mon 9/141:10 pm
ORD
-
BTV
Nonstop2h 27m
American Airlines
Deal found 2/23$210
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 4/27:00 pm
BTV
-
ORD
1 stop5h 37m
United Airlines
Mon 4/68:05 am
ORD
-
BTV
Nonstop2h 17m
United Airlines
Deal found 2/20$219
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:13 pm
BTV
-
ORD
Nonstop2h 54m
American Airlines
Wed 4/298:53 pm
ORD
-
BTV
Nonstop2h 26m
American Airlines
Deal found 2/21$220
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 4/27:10 am
BTV
-
MDW
1 stop6h 19m
Delta
Mon 4/66:34 pm
MDW
-
BTV
1 stop3h 29m
Delta
Deal found 2/20$229
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 4/87:10 am
BTV
-
ORD
1 stop7h 07m
Delta
Sat 4/115:40 pm
ORD
-
BTV
1 stop4h 23m
Delta
Deal found 2/20$229
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 7/27:42 pm
BTV
-
ORD
1 stop4h 44m
United Airlines
Mon 7/66:25 pm
ORD
-
BTV
Nonstop2h 20m
United Airlines
Deal found 2/20$230
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/97:00 pm
BTV
-
ORD
1 stop5h 37m
United Airlines
Mon 4/136:15 pm
ORD
-
BTV
Nonstop2h 20m
United Airlines
Deal found 2/23$231
This Delta deal was found by Cheapflights users on 2/23. 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 4/86:02 am
BTV
-
MDW
2 stops7h 27m
Delta
Sat 4/116:34 pm
MDW
-
BTV
1 stop3h 29m
Delta
Deal found 2/23$234
This United Airlines deal was found by Cheapflights users on 2/20. 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 5/27:19 pm
BTV
-
ORD
1 stop5h 18m
United Airlines
Sun 5/37:30 am
ORD
-
BTV
Nonstop2h 20m
United Airlines
Deal found 2/20$238
This Delta deal was found by Cheapflights users on 2/22. 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.
Tue 8/256:00 am
BTV
-
MDW
2 stops7h 30m
Delta
Sat 8/291:00 pm
MDW
-
BTV
2 stops9h 48m
Delta
Deal found 2/22$239
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 8/55:32 pm
BTV
-
ORD
1 stop6h 53m
American Airlines
Sat 8/88:20 pm
ORD
-
BTV
Nonstop2h 24m
American Airlines
Deal found 2/20$239

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 February 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$70
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$368

Good round-trip deal

$366 or less

Good one-way deal

$280 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. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 24, 2026.
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

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 3/21

6:00 am-7:43 am

Nonstop2h 43m

Chicago O'Hare Intl

Sat 3/28

6:12 pm-9:20 pm

Nonstop2h 08m

$209

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 5/23

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Sun 5/24

7:45 am-11:15 am

Nonstop2h 30m

$209

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 4/2

7:10 am-12:29 pm

1 stop6h 19m

Chicago Midway

Mon 4/6

6:34 pm-11:03 pm

1 stop3h 29m

$229

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 5/23

7:30 am-4:51 pm

2 stops10h 21m

Chicago O'Hare Intl

Sun 5/24

6:07 am-1:40 pm

1 stop6h 33m

$234

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 5/2

7:19 pm-11:37 pm

1 stop5h 18m

Chicago O'Hare Intl

Sun 5/3

7:30 am-10:50 am

Nonstop2h 20m

$238

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 3/21

7:10 am-12:29 pm

1 stop6h 19m

Chicago Midway

Mon 3/23

6:34 pm-11:03 pm

1 stop3h 29m

$249

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 7/23

12:45 pm-2:34 pm

Nonstop2h 49m

Chicago O'Hare Intl

Sun 7/26

6:25 pm-9:45 pm

Nonstop2h 20m

$263

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 5/13

7:30 am-12:42 pm

1 stop6h 12m

Chicago Midway

Mon 5/18

6:36 pm-11:02 pm

1 stop3h 26m

$268

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 7/9

7:00 am-12:39 pm

1 stop6h 39m

Chicago O'Hare Intl

Tue 7/14

3:35 pm-11:48 pm

1 stop7h 13m

$268

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 4/2

7:00 pm-11:37 pm

1 stop5h 37m

Chicago O'Hare Intl

Mon 4/6

6:01 pm-11:59 pm

1 stop4h 58m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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 $316). 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 February 24, 2026.

When flying from Vermont to Chicago, 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 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 February 24, 2026.

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 (3 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 43m. 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 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 (83%), United Airlines (73%) 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 $147. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $164 on average, our data indicates $951 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 $316). 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 February 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$308FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$221Average$372FlexibilityNo cancel feeOn-time69%

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