How many flights depart from Vermont to Chicago on average per day?

The number of flights available between Vermont and Chicago is 48 per day as of November 2025. The most frequent departure time is 4:00PM, with 75% of daily flights leaving in the afternoon.

How many flights depart from Vermont to Chicago on average per week?

341 flights are operational weekly from Vermont to Chicago as of November 2025. The most popular departure day for this route is Wed, with 16% of flights per week taking off on this day.

What is the cheapest airline that flies from Vermont to Chicago?

Frontier, United Airlines, and Delta are the most popular carriers operating from Vermont to Chicago

How long does it take to fly to Chicago?

Average flight duration from Vermont to Chicago depends on which airport you fly into and out of. Flying from Burlington to Chicago O'Hare Intl Airport is 2h 37m on average, while flying from Rutland to Chicago O'Hare Intl Airport is 5h 23m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

When did momondo last update prices for flights from Vermont to Chicago?

Prices for flights from Vermont to Chicago refresh daily.

How many operators does momondo search for flights from Vermont to Chicago?

As of November 2025, there are 5 operators available to choose from for flights from Vermont to Chicago.

How old do you have to be to fly from Vermont to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vermont to Chicago.

What documentation or ID do you need to fly to Chicago?

The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$69 Cheap Flights from Vermont to Chicago in 2025/26

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Find the cheapest flights from Vermont to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:10 am - 6:45 amBDL-MDW

2h 35mnonstop

6:05 pm - 9:05 pmMDW-BDL

2h 00mnonstop

$225Southwest

Find Deal

Sun, Feb 22 - Sat, Feb 28

11:59 am - 10:24 pmBDL-ORD

11h 25m1 stop

6:11 am - 5:26 pmORD-BDL

10h 15m2 stops

$225Multiple Airlines

Find Deal

Fri, Dec 12 - Mon, Dec 15

7:25 am - 1:00 pmBDL-MDW

6h 35m2 stops

12:55 pm - 8:05 pmMDW-BDL

6h 10m1 stop

$227Southwest

Find Deal

Thu, Dec 11 - Tue, Dec 16

12:05 pm - 5:38 pmBDL-MDW

6h 33m1 stop

6:15 am - 3:29 pmMDW-BDL

8h 14m1 stop

$228Frontier

Find Deal

Thu, Dec 18 - Mon, Dec 22

5:52 am - 7:55 amBDL-ORD

3h 03mnonstop

8:35 pm - 11:56 pmORD-BDL

2h 21mnonstop

$231American Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

5:52 am - 7:55 amBDL-ORD

3h 03mnonstop

8:35 pm - 11:56 pmORD-BDL

2h 21mnonstop

$233American Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 7

7:05 am - 4:45 pmBTV-ORD

10h 40m2 stops

6:00 am - 4:15 pmORD-BTV

9h 15m2 stops

$239Delta

Find Deal

Tue, Dec 2 - Tue, Dec 9

5:30 am - 8:54 amBDL-MDW

4h 24m1 stop

12:46 pm - 9:32 pmMDW-BDL

7h 46m1 stop

$245Delta

Find Deal

Tue, Mar 3 - Wed, Mar 4

6:15 am - 7:59 amBTV-ORD

2h 44mnonstop

5:50 pm - 8:58 pmORD-BTV

2h 08mnonstop

$247United Airlines

Find Deal

Fri, Dec 5 - Fri, Dec 12

6:12 am - 8:05 amBTV-ORD

2h 53mnonstop

10:42 am - 1:57 pmORD-BTV

2h 15mnonstop

$248United Airlines

Find Deal

Sun, Jan 18 - Fri, May 8

Delta flights from Vermont to Chicago

Our best Delta deals on Vermont to Chicago flight tickets

Delta

Dec 2

BTV7:05 amBurlington

10h 40m

2 stops

ORD4:45 pmChicago O'Hare Intl

Dec 9

ORD6:00 amChicago O'Hare Intl

9h 15m

2 stops

BTV4:15 pmBurlington

$239

Find similar

Delta

Nov 24

BDL2:20 pmHartford Bradley Intl

5h 32m

1 stop

ORD6:52 pmChicago O'Hare Intl

Dec 3

ORD9:49 amChicago O'Hare Intl

5h 20m

1 stop

BDL4:09 pmHartford Bradley Intl

$245

Find similar

Delta

Nov 24

ALB1:50 pmAlbany Intl

5h 30m

1 stop

ORD6:20 pmChicago O'Hare Intl

Nov 27

ORD5:23 amChicago O'Hare Intl

6h 50m

1 stop

ALB1:13 pmAlbany Intl

$251

Find similar

United Airlines flights from Vermont to Chicago

Our best United Airlines deals on Vermont to Chicago flight tickets

United Airlines

Nov 24

BDL7:55 pmHartford Bradley Intl

4h 49m

1 stop

ORD11:44 pmChicago O'Hare Intl

Dec 3

ORD6:13 pmChicago O'Hare Intl

2h 18m

BDL9:31 pmHartford Bradley Intl

$235

Find similar

United Airlines

Dec 5

BTV6:15 amBurlington

2h 44m

ORD7:59 amChicago O'Hare Intl

Dec 12

ORD5:50 pmChicago O'Hare Intl

2h 08m

BTV8:58 pmBurlington

$247

Find similar

United Airlines

Jan 18

BTV6:12 amBurlington

2h 53m

ORD8:05 amChicago O'Hare Intl

May 8

ORD10:42 amChicago O'Hare Intl

2h 15m

BTV1:57 pmBurlington

$248

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 2/22

5:10 am-6:45 am

Nonstop2h 35m

Chicago Midway

Sat 2/28

6:05 pm-9:05 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 12/12

11:59 am-10:24 pm

1 stop11h 25m

Chicago O'Hare Intl

Mon 12/15

6:11 am-5:26 pm

2 stops10h 15m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/11

7:25 am-1:00 pm

2 stops6h 35m

Chicago Midway

Tue 12/16

12:55 pm-8:05 pm

1 stop6h 10m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/18

12:05 pm-5:38 pm

1 stop6h 33m

Chicago Midway

Mon 12/22

6:15 am-3:29 pm

1 stop8h 14m

$228

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 12/11

5:52 am-7:55 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 12/14

8:35 pm-11:56 pm

Nonstop2h 21m

$231

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 12/7

5:52 am-7:55 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 12/7

8:35 pm-11:56 pm

Nonstop2h 21m

$233

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Tue 12/2

7:05 am-4:45 pm

2 stops10h 40m

Chicago O'Hare Intl

Tue 12/9

6:00 am-4:15 pm

2 stops9h 15m

$239

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/3

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Wed 3/4

12:46 pm-9:32 pm

1 stop7h 46m

$245

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Fri 12/5

6:15 am-7:59 am

Nonstop2h 44m

Chicago O'Hare Intl

Fri 12/12

5:50 pm-8:58 pm

Nonstop2h 08m

$247

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sun 1/18

6:12 am-8:05 am

Nonstop2h 53m

Chicago O'Hare Intl

Fri 5/8

10:42 am-1:57 pm

Nonstop2h 15m

$248

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How to get the cheapest flight ticket from Vermont to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Vermont, with most prices found around $279. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Vermont to Chicago during October average around $293.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $445. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Vermont to Chicago for around $640.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Vermont to Chicago during this time can be as low as $339. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $505.

What is the cheapest Vermont to Chicago flight route?

Fly from Burlington to Chicago O'Hare Intl for the best Vermont - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Vermont when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $359 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Vermont for as low as $242 on momondo.

What cabin class options are available on Vermont to Chicago flights?

There are 4 cabin classes available to choose from on Vermont to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Vermont to Chicago flights?

You could potentially save up to 38% on your flight if you consider stops on a Vermont to Chicago flight.

Cheap Vermont to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vermont to Chicago

Best Price Found	$342
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Vermont in the past 72 hours is $342. The best round-trip flight deal from Vermont to Chicago found on momondo in the last 72 hours is $332.

The fastest flight from Vermont to Chicago takes 2h 10m

Direct flights go from Vermont to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Vermont to Chicago?
Prices for flights from Vermont to Chicago refresh daily.
How many operators does momondo search for flights from Vermont to Chicago?
As of November 2025, there are 5 operators available to choose from for flights from Vermont to Chicago.
How old do you have to be to fly from Vermont to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vermont to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Vermont to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Vermont to Chicago is Boeing 737 MAX 9 (20.35% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (16.63%), Boeing 737-800 (15.23%), and Canadair (Bombardier) Regional Jet 700 (14.07%).

Best airlines flying from Vermont to Chicago

Compare and see reviews for airlines that fly from Vermont to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.2 11,051 reviews		Search American Airlines flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 9,017 reviews		Search United Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Vermont to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Vermont to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Vermont to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Vermont with this policy.

How can momondo help me find flights from Vermont to Chicago?

momondo helps you find the best flight between Vermont and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Vermont to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Vermont to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Cheap flights from Vermont to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Vermont to Chicago departing on 11/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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Find the cheapest flights from Vermont to Chicago

Cheap round-trip flights

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Delta flights from Vermont to Chicago

Our best Delta deals on Vermont to Chicago flight tickets

United Airlines flights from Vermont to Chicago

Our best United Airlines deals on Vermont to Chicago flight tickets

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Use the filters below to find and compare flights from Vermont to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Vermont to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Vermont, with most prices found around $279. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Vermont to Chicago during October average around $293.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Vermont to Chicago during this time can be as low as $339. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $505.

What is the cheapest Vermont to Chicago flight route?

Fly from Burlington to Chicago O'Hare Intl for the best Vermont - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Vermont to Chicago flights?

There are 4 cabin classes available to choose from on Vermont to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Vermont to Chicago flights?

You could potentially save up to 38% on your flight if you consider stops on a Vermont to Chicago flight.

What is the cheapest airline that flies from Vermont to Chicago?

Frontier, United Airlines, and Delta are the most popular carriers operating from Vermont to Chicago

How many flights depart from Vermont to Chicago on average per day?

The number of flights available between Vermont and Chicago is 48 per day as of November 2025. The most frequent departure time is 4:00PM, with 75% of daily flights leaving in the afternoon.

How many flights depart from Vermont to Chicago on average per week?

341 flights are operational weekly from Vermont to Chicago as of November 2025. The most popular departure day for this route is Wed, with 16% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Vermont to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vermont to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Vermont to Chicago?

How many operators does momondo search for flights from Vermont to Chicago?

How old do you have to be to fly from Vermont to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Vermont to Chicago?

Best airlines flying from Vermont to Chicago

Compare and see reviews for airlines that fly from Vermont to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Vermont to Chicago?

Can I find flights from Vermont to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Vermont to Chicago?

I’m not ready to book a flight from Vermont to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago