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$55+ 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
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$222
(Southwest)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

January

Average price

$444

Good round-trip deal

$403 or less

Good one-way deal

$248 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. 10% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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).
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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 February 20, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/301:25 pmBDL - MDW
2 stops8h 45mSouthwest
Fri 5/29:50 amMDW - BDL
1 stop5h 25mSouthwest
Deal found 2/20$222
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/911:36 amBDL - ORD
2 stops21h 45mSpirit Airlines
Tue 3/115:55 amORD - BDL
2 stops27h 46mSpirit Airlines
Deal found 2/20$224
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/251:59 pmBDL - ORD
2 stops19h 05mMultiple Airlines
Mon 4/2810:26 pmORD - BDL
3 stops34h 14mMultiple Airlines
Deal found 2/20$236
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.
Fri 4/255:40 amBDL - MDW
1 stop4h 00mDelta
Mon 4/285:59 pmMDW - BDL
1 stop4h 11mDelta
Deal found 2/20$237
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/183:13 pmBDL - MDW
1 stop9h 37mFrontier
Mon 4/217:05 amMDW - BDL
1 stop6h 20mFrontier
Deal found 2/20$240
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/257:23 amBDL - ORD
Nonstop2h 39mAmerican Airlines
Wed 4/306:45 amORD - BDL
1 stop4h 25mAmerican Airlines
Deal found 2/19$242
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/36:15 amBDL - ORD
Nonstop2h 43mUnited Airlines
Mon 4/77:25 amORD - BDL
Nonstop2h 15mUnited Airlines
Deal found 2/19$247
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/21:04 pmBDL - ORD
1 stop21h 23mFrontier
Mon 3/37:08 pmORD - BDL
1 stop16h 33mFrontier
Deal found 2/20$270
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/202:30 pmALB - MDW
2 stops6h 20mSouthwest
Thu 3/277:15 amMDW - ALB
1 stop5h 25mSouthwest
Deal found 2/20$272
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.
Sun 3/235:30 amALB - ORD
1 stop6h 09mAmerican Airlines
Sat 3/296:29 pmORD - ALB
Nonstop2h 08mAmerican Airlines
Deal found 2/20$273
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/176:00 amALB - ORD
Nonstop2h 31mUnited Airlines
Sun 4/2011:47 amORD - ALB
Nonstop2h 06mUnited Airlines
Deal found 2/19$275
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3111:42 amBDL - ORD
1 stop8h 29mSun Country Air
Sun 8/38:10 pmORD - BDL
1 stop13h 37mSun Country Air
Deal found 2/20$275

Find flights from Vermont to Chicago within your budget

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 20, 2025.

Fly from

Vermont

Fly to

Chicago

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 4/30

1:25 pm-9:10 pm

2 stops8h 45m

Chicago Midway

Fri 5/2

9:50 am-4:15 pm

1 stop5h 25m

$222

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 5/10

8:20 am-4:45 pm

2 stops9h 25m

Chicago O'Hare Intl

Wed 5/14

1:50 pm-7:45 pm

1 stop4h 55m

$222

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 3/6

12:21 pm-2:15 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 3/10

2:36 pm-10:26 pm

1 stop6h 50m

$223

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 3/9

11:36 am-8:21 am

2 stops21h 45m

Chicago O'Hare Intl

Tue 3/11

5:55 am-10:41 am

2 stops27h 46m

$224

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 4/3

6:30 am-9:45 am

2 stops28h 15m

Chicago O'Hare Intl

Mon 4/7

7:10 pm-9:57 pm

1 stop25h 47m

$231

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/25

5:40 am-8:40 am

1 stop4h 00m

Chicago Midway

Mon 4/28

5:59 pm-11:10 pm

1 stop4h 11m

$237

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 3/22

3:00 pm-8:13 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 3/29

5:30 pm-12:11 am

1 stop5h 41m

$237

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/18

3:13 pm-11:50 pm

1 stop9h 37m

Chicago Midway

Mon 4/21

7:05 am-2:25 pm

1 stop6h 20m

$240

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 4/3

6:15 am-7:58 am

Nonstop2h 43m

Chicago O'Hare Intl

Mon 4/7

7:25 am-10:40 am

Nonstop2h 15m

$247

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 3/2

1:04 pm-9:27 am

1 stop21h 23m

Chicago O'Hare Intl

Mon 3/3

7:08 pm-12:41 pm

1 stop16h 33m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 58 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.

Travel insights for flights from Vermont to Chicago

Get recent, data-driven insights about flights from Vermont to Chicago including ideal travel times, pricing trends, and more.

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 February 20, 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.

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 20, 2025.

The most flights from USVT to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
Read through reviews of airlines operating flights from Vermont to Chicago, such as Southwest, Delta and JetBlue. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier. According to our data, you can fly for as low as $55. Users have also found prices from $70 and $89 on Spirit Airlines and United Airlines, 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 Emirates (84%), Air New Zealand (83%) or Republic Airways (82%) 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 $124. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $147 on average our data indicates $1,002 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 Vermont?

Book flights to Vermont if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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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Denver to Midway flights

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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$259Average$381FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$267Average$339FlexibilityNo cancel feeOn-time71%
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