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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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Vermont to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Vermont (USVT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$269
(Booking.com)

One-way from

$61
(Frontier)

Good round-trip deal

$412 or less

Good one-way deal

$269 or less
From Vermont to Chicago (CHI)
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One-way flight from Vermont to Chicago (CHI)
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Price to beat on a round-trip flight from Vermont to Chicago (CHI).
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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 January 21, 2025.

This Gotogate deal was found by Cheapflights users on 1/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/2711:25 amBTV - ORD
1 stop11h 51mFrontier
Thu 1/306:50 amORD - BTV
1 stop25h 40mFrontier
Deal found 1/21$253
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/306:25 pmBTV - MDW
1 stop21h 17mFrontier
Sun 2/28:45 amMDW - BTV
1 stop24h 40mFrontier
Deal found 1/21$269
This Delta deal was found by Cheapflights users on 1/21. 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.
Tue 2/116:10 amBDL - MDW
1 stop6h 49mDelta
Tue 2/185:05 pmMDW - BDL
1 stop6h 04mDelta
Deal found 1/21$277
This Delta deal was found by Cheapflights users on 1/21. 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.
Thu 2/137:20 amBDL - ORD
1 stop7h 29mDelta
Mon 2/176:59 amORD - BDL
1 stop4h 11mDelta
Deal found 1/21$277
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Sat 2/88:00 amBDL - ORD
3 stops16h 32mMultiple Airlines
Mon 2/106:15 pmORD - BDL
1 stop17h 50mMultiple Airlines
Deal found 1/20$278
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Fri 8/297:35 amBTV - ORD
Nonstop2h 35mAmerican Airlines
Tue 9/26:20 pmORD - BTV
Nonstop2h 15mAmerican Airlines
Deal found 1/21$279
This Frontier deal was found by Cheapflights users on 1/20. 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 3/72:59 pmBDL - MDW
1 stop9h 59mFrontier
Mon 3/246:20 amMDW - BDL
1 stop6h 39mFrontier
Deal found 1/20$280
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2811:42 amBDL - ORD
1 stop22h 33mFrontier
Sun 3/28:14 amORD - BDL
1 stop26h 55mFrontier
Deal found 1/21$280
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1811:17 amBDL - ORD
2 stops24h 48mSpirit Airlines
Tue 2/255:15 amORD - BDL
3 stops28h 07mSpirit Airlines
Deal found 1/21$283
This Southwest deal was found by Cheapflights users on 1/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/26:00 amBDL - MDW
Nonstop2h 30mSouthwest
Fri 4/44:45 pmMDW - BDL
1 stop4h 10mSouthwest
Deal found 1/21$287
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 4/812:35 pmBDL - ORD
1 stop6h 01mAmerican Airlines
Fri 4/117:06 pmORD - BDL
Nonstop2h 17mAmerican Airlines
Deal found 1/21$287
This United Airlines deal was found by Cheapflights users on 1/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/26:09 amALB - ORD
Nonstop2h 48mUnited Airlines
Mon 3/34:10 pmORD - ALB
1 stop6h 34mUnited Airlines
Deal found 1/21$289

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Fri 2/14

2:01 pm-1:10 pm

1 stop24h 09m

Chicago O'Hare Intl

Mon 2/17

5:10 am-1:11 pm

1 stop7h 01m

$269

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 2/11

6:10 am-11:59 am

1 stop6h 49m

Chicago Midway

Tue 2/18

5:05 pm-12:09 am

1 stop6h 04m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 2/13

7:20 am-1:49 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 2/17

6:59 am-12:10 pm

1 stop4h 11m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 2/8

8:00 am-11:32 pm

3 stops16h 32m

Chicago O'Hare Intl

Mon 2/10

6:15 pm-1:05 pm

1 stop17h 50m

$278

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 3/6

11:36 am-12:07 am

1 stop13h 31m

Chicago O'Hare Intl

Thu 3/13

5:22 pm-10:41 am

2 stops16h 19m

$279

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 3/7

2:59 pm-11:58 pm

1 stop9h 59m

Chicago Midway

Mon 3/24

6:20 am-1:59 pm

1 stop6h 39m

$280

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 2/28

11:42 am-9:15 am

1 stop22h 33m

Chicago O'Hare Intl

Sun 3/2

8:14 am-12:09 pm

1 stop26h 55m

$280

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 4/2

6:00 am-7:30 am

Nonstop2h 30m

Chicago Midway

Fri 4/4

4:45 pm-9:55 pm

1 stop4h 10m

$287

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 4/8

12:35 pm-5:36 pm

1 stop6h 01m

Chicago O'Hare Intl

Fri 4/11

7:06 pm-10:23 pm

Nonstop2h 17m

$287

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Sun 3/2

6:09 am-7:57 am

Nonstop2h 48m

Chicago O'Hare Intl

Mon 3/3

4:10 pm-11:44 pm

1 stop6h 34m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 $320). 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 January 21, 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 January 21, 2025.

The most flights from USVT to CHI are scheduled on a Wednesday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 January 21, 2025.
Read through reviews of airlines operating flights from Vermont to Chicago, such as American Airlines, United Airlines and Frontier. 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
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $61. Users have also found prices from $74 and $125 on Spirit Airlines and American 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%), Republic Airways (82%) or Air Canada (76%) 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 $174. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $155 on average our data indicates $1,055 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 $320). 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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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$227Average$327FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$259Average$390FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$261Average$339FlexibilityNo cancel feeOn-time71%
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