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

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

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

As of August 2026, there are 44 flights per day flying from Chicago to Vermont. The most common time of day flights depart is 6:00PM, with 50% of flights taking off in the evening.

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

312 flights are operational weekly from Chicago to Vermont as of August 2026. The most popular departure day for this route is Wed, with 20% of flights per week taking off on this day.

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

Prices for flights from Chicago to Vermont were last updated today.

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

The number of operators available for flights from Chicago to Vermont is 3 as of August 2026.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Vermont.

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

The travel and health documents required for your trip to Vermont can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Vermont. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$90 Cheap Flights from Chicago to Vermont in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Vermont

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:45 am - 10:45 amMDW Chicago Midway-ALB Albany Intl

2h 00mnonstop

7:25 am - 8:35 amALB Albany Intl-MDW Chicago Midway

2h 10mnonstop

$257Southwest

Sat, Sep 19 - Sat, Sep 26

6:50 pm - 9:45 pmMDW Chicago Midway-ALB Albany Intl

1h 55mnonstop

7:15 pm - 8:25 pmALB Albany Intl-MDW Chicago Midway

2h 10mnonstop

$257Southwest

Thu, Oct 22 - Mon, Oct 26

11:59 am - 3:04 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 05mnonstop

4:53 pm - 6:30 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 37mnonstop

$257United Airlines

Wed, Sep 9 - Wed, Sep 16

11:59 am - 3:04 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 05mnonstop

8:10 am - 9:44 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 34mnonstop

$257United Airlines

Wed, Sep 9 - Tue, Sep 15

9:00 pm - 12:18 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 18mnonstop

7:20 pm - 9:12 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$257American Airlines

Thu, Oct 1 - Mon, Oct 5

8:15 am - 11:35 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 20mnonstop

6:36 pm - 8:30 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

$257American Airlines

Wed, Sep 9 - Tue, Sep 15

6:20 pm - 9:25 pmMDW Chicago Midway-ALB Albany Intl

2h 05mnonstop

6:20 pm - 7:25 pmALB Albany Intl-MDW Chicago Midway

2h 05mnonstop

$257Southwest

Wed, Sep 9 - Tue, Sep 15

7:15 pm - 10:37 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 22mnonstop

8:05 pm - 10:00 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

$257American Airlines

Tue, Dec 22 - Tue, Dec 29

7:11 am - 10:25 amORD Chicago O'Hare Intl-ALB Albany Intl

26h 14m1 stop Fort Lauderdale

8:18 pm - 10:59 pmALB Albany Intl-ORD Chicago O'Hare Intl

27h 41m2 stops Charleston Orlando

$262Multiple Airlines

Wed, Sep 23 - Mon, Sep 28

2:35 pm - 11:55 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

8h 20m1 stop Fort Lauderdale

3:16 pm - 7:31 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

17h 15m1 stop Orlando

$277Multiple Airlines

Thu, Oct 15 - Mon, Oct 19

Cheap last minute flights

Enter your travel dates to find the best prices.

5:59 pm - 11:32 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

16h 33m1 stop Orlando

12:27 pm - 11:08 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

11h 41m1 stop Orlando

$350Frontier

Tue, Aug 25 - Fri, Aug 28

7:30 am - 11:03 amORD Chicago O'Hare Intl-BTV Burlington

2h 33mnonstop

4:47 pm - 6:31 pmBTV Burlington-ORD Chicago O'Hare Intl

2h 44mnonstop

$354United Airlines

Tue, Aug 25 - Tue, Sep 1

5:27 pm - 12:20 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

5h 53m1 stop New York John F Kennedy Intl

1:42 pm - 11:27 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

10h 45m1 stop San Juan Luis Munoz Marin Intl

$358Multiple Airlines

Mon, Aug 24 - Tue, Aug 25

10:55 am - 2:17 pmORD Chicago O'Hare Intl-BTV Burlington

2h 22mnonstop

7:40 pm - 11:40 pmBTV Burlington-ORD Chicago O'Hare Intl

5h 00m1 stop Washington, D.C. Dulles Intl

$364United Airlines

Tue, Aug 25 - Tue, Sep 1

8:00 am - 4:46 pmORD Chicago O'Hare Intl-BTV Burlington

7h 46m1 stop Washington, D.C. Reagan-National

5:16 pm - 11:37 pmBTV Burlington-ORD Chicago O'Hare Intl

7h 21m1 stop Washington, D.C. Reagan-National

$374American Airlines

Tue, Aug 25 - Tue, Sep 1

6:42 pm - 11:21 pmMDW Chicago Midway-BTV Burlington

3h 39m1 stop Detroit Metropolitan Wayne County

5:14 am - 9:59 amBTV Burlington-MDW Chicago Midway

5h 45m1 stop Atlanta Hartsfield-Jackson

$374Delta

Tue, Aug 25 - Tue, Sep 1

4:24 pm - 7:41 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 17mnonstop

3:38 pm - 5:29 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

$432American Airlines

Mon, Aug 24 - Wed, Aug 26

7:45 am - 10:45 amMDW Chicago Midway-ALB Albany Intl

2h 00mnonstop

3:55 pm - 5:00 pmALB Albany Intl-MDW Chicago Midway

2h 05mnonstop

$447Southwest

Sat, Aug 22 - Sat, Aug 29

7:45 am - 10:45 amMDW Chicago Midway-ALB Albany Intl

2h 00mnonstop

11:25 am - 4:40 pmALB Albany Intl-MDW Chicago Midway

6h 15m1 stop Baltimore/Washington

$457Southwest

Sat, Aug 22 - Sat, Aug 29

7:15 am - 10:24 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 09mnonstop

6:00 am - 7:31 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 31mnonstop

$497United Airlines

Fri, Aug 21 - Sun, Aug 23

Cheap direct flights

Enter your travel dates to find the best prices.

8:39 pm - 11:59 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 20mnonstop

7:20 pm - 9:12 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$257American Airlines

Wed, Oct 14 - Mon, Oct 19

3:32 pm - 6:53 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 21mnonstop

7:20 pm - 9:12 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$257American Airlines

Thu, Oct 15 - Mon, Oct 19

6:10 pm - 9:26 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 16mnonstop

9:05 am - 11:05 amALB Albany Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

$257United Airlines

Wed, Dec 23 - Thu, Dec 31

7:15 am - 10:24 amORD Chicago O'Hare Intl-ALB Albany Intl

2h 09mnonstop

4:53 pm - 6:30 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 37mnonstop

$257United Airlines

Thu, Sep 17 - Mon, Sep 21

7:45 am - 10:45 amMDW Chicago Midway-ALB Albany Intl

2h 00mnonstop

7:25 am - 8:35 amALB Albany Intl-MDW Chicago Midway

2h 10mnonstop

$257Southwest

Sat, Sep 19 - Sat, Sep 26

6:50 pm - 9:45 pmMDW Chicago Midway-ALB Albany Intl

1h 55mnonstop

7:15 pm - 8:25 pmALB Albany Intl-MDW Chicago Midway

2h 10mnonstop

$257Southwest

Thu, Oct 22 - Mon, Oct 26

8:39 pm - 11:59 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 20mnonstop

7:23 am - 9:10 amALB Albany Intl-ORD Chicago O'Hare Intl

2h 47mnonstop

$257American Airlines

Sat, Oct 10 - Mon, Oct 12

6:20 pm - 9:25 pmMDW Chicago Midway-ALB Albany Intl

2h 05mnonstop

6:20 pm - 7:25 pmALB Albany Intl-MDW Chicago Midway

2h 05mnonstop

$257Southwest

Wed, Sep 9 - Tue, Sep 15

3:32 pm - 6:53 pmORD Chicago O'Hare Intl-ALB Albany Intl

2h 21mnonstop

7:39 pm - 9:31 pmALB Albany Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$257American Airlines

Thu, Oct 22 - Mon, Oct 26

7:25 am - 10:48 amORD Chicago O'Hare Intl-BTV Burlington

2h 23mnonstop

6:10 am - 7:49 amBTV Burlington-ORD Chicago O'Hare Intl

2h 39mnonstop

$279United Airlines

Sat, Oct 10 - Sat, Oct 17

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Frontier flights from Chicago to Vermont

Our best Frontier deals on Chicago to Vermont flight tickets

Frontier

Oct 10

ORD9:00 amChicago O'Hare Intl

28h 21m

1 stop

BDL2:21 pmHartford Bradley Intl

Oct 12

BDL3:16 pmHartford Bradley Intl

17h 15m

1 stop

ORD7:31 amChicago O'Hare Intl

$279

Frontier

Sep 4

ORD9:10 pmChicago O'Hare Intl

13h 22m

1 stop

BDL11:32 amHartford Bradley Intl

Sep 6

BDL12:27 pmHartford Bradley Intl

11h 41m

1 stop

ORD11:08 pmChicago O'Hare Intl

$281

Frontier

Oct 15

ORD5:54 pmChicago O'Hare Intl

19h 27m

1 stop

BDL2:21 pmHartford Bradley Intl

Oct 18

BDL3:16 pmHartford Bradley Intl

17h 15m

1 stop

ORD7:31 amChicago O'Hare Intl

$291

Southwest flights from Chicago to Vermont

Our best Southwest deals on Chicago to Vermont flight tickets

Southwest

Sep 10

MDW8:05 amChicago Midway

2h 05m

ALB11:10 amAlbany Intl

Sep 14

ALB6:05 pmAlbany Intl

2h 10m

MDW7:15 pmChicago Midway

$257

Southwest

Sep 30

MDW6:30 amChicago Midway

4h 45m

1 stop

ALB12:15 pmAlbany Intl

Oct 7

ALB6:25 pmAlbany Intl

2h 10m

MDW7:35 pmChicago Midway

$267

Southwest

Sep 10

MDW8:05 amChicago Midway

2h 05m

ALB11:10 amAlbany Intl

Sep 14

ALB6:05 pmAlbany Intl

2h 10m

MDW7:15 pmChicago Midway

$268

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAlbany

MDW Chicago Midway - ALB Albany Intl

MDWALB

Chicago Midway

Sat 9/19

7:45 am-10:45 am

Nonstop2h 00m

Albany Intl

Sat 9/26

7:25 am-8:35 am

Nonstop2h 10m

$257

Quickest round-trip

ChicagoAlbany

MDW Chicago Midway - ALB Albany Intl

MDWALB

Chicago Midway

Thu 10/22

6:50 pm-9:45 pm

Nonstop1h 55m

Albany Intl

Mon 10/26

7:15 pm-8:25 pm

Nonstop2h 10m

$257

ChicagoAlbany

ORD Chicago O'Hare Intl - ALB Albany Intl

ORDALB

Chicago O'Hare Intl

Wed 9/9

11:59 am-3:04 pm

Nonstop2h 05m

Albany Intl

Wed 9/16

4:53 pm-6:30 pm

Nonstop2h 37m

$257

ChicagoAlbany

ORD Chicago O'Hare Intl - ALB Albany Intl

ORDALB

Chicago O'Hare Intl

Wed 9/9

11:59 am-3:04 pm

Nonstop2h 05m

Albany Intl

Tue 9/15

8:10 am-9:44 am

Nonstop2h 34m

$257

ChicagoAlbany

ORD Chicago O'Hare Intl - ALB Albany Intl

ORDALB

Chicago O'Hare Intl

Thu 10/1

9:00 pm-12:18 am

Nonstop2h 18m

Albany Intl

Mon 10/5

7:20 pm-9:12 pm

Nonstop2h 52m

$257

ChicagoAlbany

ORD Chicago O'Hare Intl - ALB Albany Intl

ORDALB

Chicago O'Hare Intl

Wed 9/9

8:15 am-11:35 am

Nonstop2h 20m

Albany Intl

Tue 9/15

6:36 pm-8:30 pm

Nonstop2h 54m

$257

ChicagoAlbany

MDW Chicago Midway - ALB Albany Intl

MDWALB

Chicago Midway

Wed 9/9

6:20 pm-9:25 pm

Nonstop2h 05m

Albany Intl

Tue 9/15

6:20 pm-7:25 pm

Nonstop2h 05m

$257

ChicagoAlbany

ORD Chicago O'Hare Intl - ALB Albany Intl

ORDALB

Chicago O'Hare Intl

Tue 12/22

7:15 pm-10:37 pm

Nonstop2h 22m

Albany Intl

Tue 12/29

8:05 pm-10:00 pm

Nonstop2h 55m

$257

ChicagoAlbany

ORD Chicago O'Hare Intl - ALB Albany Intl

ORDALB

Chicago O'Hare Intl

Wed 9/23

7:11 am-10:25 am

1 stop26h 14m

Albany Intl

Mon 9/28

8:18 pm-10:59 pm

2 stops27h 41m

$262

ChicagoHartford

ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl

ORDBDL

Chicago O'Hare Intl

Thu 10/15

2:35 pm-11:55 pm

1 stop8h 20m

Hartford Bradley Intl

Mon 10/19

3:16 pm-7:31 am

1 stop17h 15m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Vermont

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 Vermont?

In general, March is the cheapest month to fly from Chicago to Vermont. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $306. The month of September is another great option to travel to Vermont, with average flight prices from Chicago averaging around $339.

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

The cheapest day to depart on your flight to Vermont is on a Wednesday when prices can be found for as low as $296. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Vermont is Sunday, with ticket prices averaging around $459.

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

In the evening is the cheapest time of day to fly from Chicago to Vermont when you can find flight prices for as low as $319. Flying to Vermont in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $375. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Vermont flight route?

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

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

You are more likely to see cheaper flights to Vermont from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Vermont for around $386 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Vermont from Chicago for as low as $269 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Vermont 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 Chicago to Vermont flights?

You could potentially save up to 34% on your flight if you consider stops on a Chicago to Vermont flight.

Cheap Chicago to Vermont flight deals and tips

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

Best Price Found	$90
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Vermont	43 airports

The best one-way flight to Vermont from Chicago in the past 72 hours is $90. The best round-trip flight deal from Chicago to Vermont found on momondo in the last 72 hours is $257.

The fastest flight from Chicago to Vermont takes 1h 50m

Direct flights go from Chicago to Vermont every day.

There are 43 airports in Vermont. From Chicago there are direct flights to Burlington (BTV), Albany Intl (ALB), Hartford Bradley Intl (BDL).

Search flight deals

Frequently asked questions about flying from Chicago to Vermont

When did momondo last update prices for flights from Chicago to Vermont?
Prices for flights from Chicago to Vermont were last updated today.
How many operators does momondo search for flights from Chicago to Vermont?
The number of operators available for flights from Chicago to Vermont is 3 as of August 2026.
How old do you have to be to fly from Chicago to Vermont?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Vermont.
What documentation or ID do you need to fly to Vermont?
The travel and health documents required for your trip to Vermont can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Vermont. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Vermont?
Based on momondo bookings for flights between Chicago and Vermont, the leading plane model is Boeing 737-800, making up 27.81% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet 700 with 27.50%, Boeing 737 MAX 9 with 25.94%, and Embraer 175 (Enhanced Winglets) with 9.06%.

Best airlines flying from Chicago to Vermont

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

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 10,102 reviews		Search United Airlines flights
American Airlines	PriceFrom $229	Free Cancellation	Rating 7.1 11,968 reviews		Search American Airlines flights

Why use momondo?

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

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

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

Yes. momondo allows you to filter the results for Chicago to Vermont flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Vermont from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Vermont 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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Popular cities in Vermont

Flights to New Yorkfrom $50

Flights to Los Angelesfrom $46

Flights to Orlandofrom $53

Flights to Miamifrom $56

Flights to San Franciscofrom $46

Flights to Chicagofrom $51

Flights to Las Vegasfrom $46

Flights to Washington, D.C.from $58

Flights to Bostonfrom $65

Flights to Atlantafrom $53

Flights to Fort Lauderdalefrom $50

Flights to Dallasfrom $50

Cheap flights from Chicago to Vermont from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Vermont departing on 10/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Chicago to Vermont

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Frontier flights from Chicago to Vermont

Our best Frontier deals on Chicago to Vermont flight tickets

Southwest flights from Chicago to Vermont

Our best Southwest deals on Chicago to Vermont flight tickets

momondo Fare Finder

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

See travel insights to Vermont from

How to get the cheapest flight ticket from Chicago to Vermont

What is the cheapest month to fly to Vermont?

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

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

What is the cheapest Chicago to Vermont flight route?

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

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

Can stopping save me money on Chicago to Vermont flights?

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

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

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

Cheap Chicago to Vermont flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Vermont

Frequently asked questions about flying from Chicago to Vermont

Best airlines flying from Chicago to Vermont

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

Why use momondo?

An easier way to manage your Vermont 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 Vermont

Popular cities in Vermont

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

According to popular flight searches on momondo this year

Vermont flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Vermont

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