HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Vermont to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 18, 2025.

Round-trip from

$171
(FlightHub)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

May

Average price

$359

Good round-trip deal

$376 or less

Good one-way deal

$229 or less
From Vermont to Chicago (CHI)
Search Deals
One-way flight from Vermont to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
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

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 August 18, 2025.

This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:04 amBDL - MDW
1 stop14h 21mFrontier
Sat 10/186:15 amMDW - BDL
1 stop25h 54mFrontier
Deal found 8/17$171
This FlightHub deal was found by Cheapflights users on 8/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1110:30 amBDL - ORD
1 stop14h 40mFrontier
Sat 9/135:40 pmORD - BDL
1 stop16h 53mFrontier
Deal found 8/15$171
This United Airlines deal was found by Cheapflights users on 8/14. 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.
Tue 9/306:00 amBDL - ORD
1 stop4h 36mUnited Airlines
Tue 9/306:18 pmORD - BDL
Nonstop2h 25mUnited Airlines
Deal found 8/14$173
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:45 pmBDL - ORD
1 stop8h 37mSpirit Airlines
Sun 8/3110:12 amORD - BDL
1 stop5h 47mSpirit Airlines
Deal found 8/16$174
This FlightHub deal was found by Cheapflights users on 8/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:30 amBDL - MDW
1 stop13h 50mFrontier
Sun 9/2810:13 amMDW - BDL
1 stop8h 29mFrontier
Deal found 8/15$175
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2811:05 amBDL - ORD
1 stop8h 36mMultiple Airlines
Sun 8/3110:12 amORD - BDL
1 stop5h 47mMultiple Airlines
Deal found 8/14$176
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:52 pmBDL - ORD
1 stop19h 25mMultiple Airlines
Sun 10/51:26 pmORD - BDL
1 stop21h 23mMultiple Airlines
Deal found 8/17$179
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:45 pmBDL - ORD
1 stop8h 37mMultiple Airlines
Wed 9/34:04 pmORD - BDL
1 stop16h 31mMultiple Airlines
Deal found 8/16$181
This American Airlines deal was found by Cheapflights users on 8/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:36 amBDL - ORD
Nonstop2h 37mAmerican Airlines
Tue 9/166:40 pmORD - BDL
Nonstop2h 16mAmerican Airlines
Deal found 8/15$182
This Frontier deal was found by Cheapflights users on 8/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:30 amBDL - ORD
1 stop14h 40mFrontier
Sun 9/218:49 pmORD - BDL
1 stop22h 08mFrontier
Deal found 8/16$183
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:20 pmBDL - MDW
1 stop8h 05mFrontier
Sat 10/256:15 amMDW - BDL
1 stop25h 54mFrontier
Deal found 8/17$184
This Frontier deal was found by Cheapflights users on 8/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:04 amBDL - ORD
2 stops14h 02mFrontier
Mon 10/205:05 amORD - BDL
1 stop9h 16mFrontier
Deal found 8/16$187

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 August 18, 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

Thu 10/16

10:04 am-8:21 pm

1 stop11h 17m

Chicago Midway

Sat 10/18

6:15 am-9:09 am

1 stop25h 54m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 9/11

10:30 am-12:10 am

1 stop14h 40m

Chicago O'Hare Intl

Wed 9/17

11:45 am-9:35 am

1 stop20h 50m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 9/11

10:30 am-12:10 am

1 stop14h 40m

Chicago O'Hare Intl

Sat 9/13

5:40 pm-11:33 am

1 stop16h 53m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 10/16

10:04 am-12:11 am

1 stop15h 07m

Chicago O'Hare Intl

Mon 10/20

5:05 am-3:21 pm

1 stop9h 16m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 10/16

10:04 am-12:11 am

1 stop15h 07m

Chicago O'Hare Intl

Sat 10/18

6:00 am-9:09 am

1 stop26h 09m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 10/2

10:30 am-10:31 am

1 stop25h 01m

Chicago O'Hare Intl

Sat 10/4

5:40 pm-11:33 am

1 stop16h 53m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 9/30

6:00 am-9:36 am

1 stop4h 36m

Chicago O'Hare Intl

Tue 9/30

6:18 pm-9:43 pm

Nonstop2h 25m

$173

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 8/30

2:45 pm-10:22 pm

1 stop8h 37m

Chicago O'Hare Intl

Sun 8/31

10:12 am-4:59 pm

1 stop5h 47m

$174

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/25

10:30 am-11:20 pm

1 stop13h 50m

Chicago Midway

Sun 9/28

10:13 am-7:42 pm

1 stop8h 29m

$175

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 8/28

11:05 am-6:41 pm

1 stop8h 36m

Chicago O'Hare Intl

Sun 8/31

10:12 am-4:59 pm

1 stop5h 47m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 60 results
1
2
3
...
6

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, August is the cheapest month in which you can book a flight from Vermont to Chicago (average of $245). Flying from Vermont to Chicago in March is currently the most expensive (average of $321). 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 August 18, 2025.

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.

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.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $79. Users have also found prices from $79 and $80 on American Airlines and Spirit Airlines, 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 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 (76%), SkyWest Airlines (54%) or American Airlines (54%) 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 $132 on average our data indicates $856 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, August is the cheapest month in which you can book a flight from Vermont to Chicago (average of $245). Flying from Vermont to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Vermont to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Atlanta to Midway flights
Charlotte to O'Hare Intl flights
Baltimore to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Ontario to O'Hare Intl flights
Newark to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Orlando to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to Midway flights
Hobby to O'Hare Intl flights
Los Angeles to Midway flights
Denver to Midway flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
San Francisco to Midway flights
Burbank to O'Hare Intl flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Diego to O'Hare Intl flights
LaGuardia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Minneapolis to O'Hare Intl flights
San Jose to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Miami to O'Hare Intl flights
Denver to St. Louis flights
Seattle to Midway flights
Boston to Midway flights
Sky Harbor Intl to Midway flights
Charleston to O'Hare Intl flights

Top 3 airlines flying from Vermont to Chicago

Discover the top 3 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$125Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$310FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$360FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.