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Cheap flights from Vermont to Chicago from $68

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 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Vermont to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
10:52 am - 8:27 pm
BDL
-
MDW
10h 35m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$170Frontier
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
2:27 pm - 10:39 pm
BDL
-
ORD
9h 12m1 stop
Frontier Logo
5:05 am - 1:32 pm
ORD
-
BDL
7h 27m1 stop
$170Frontier
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
1:56 pm - 5:52 pm
BDL
-
ORD
28h 56m2 stops
Multiple Airlines Logo
12:44 pm - 7:36 pm
ORD
-
BDL
29h 52m1 stop
$197Multiple Airlines
Fri, Jan 23 - Wed, Feb 4
American Airlines Logo
6:10 pm - 8:00 pm
BTV
-
ORD
2h 50mnonstop
American Airlines Logo
2:04 pm - 5:25 pm
ORD
-
BTV
2h 21mnonstop
$209American Airlines
Wed, Apr 8 - Sat, Apr 11
Multiple Airlines Logo
10:00 am - 9:12 am
ALB
-
ORD
24h 12m2 stops
Multiple Airlines Logo
12:44 pm - 8:46 am
ORD
-
ALB
19h 02m1 stop
$210Multiple Airlines
Mon, Feb 2 - Wed, Feb 4
Southwest Logo
5:30 am - 7:05 am
BDL
-
MDW
2h 35mnonstop
Southwest Logo
1:25 pm - 4:20 pm
MDW
-
BDL
1h 55mnonstop
$215Southwest
Thu, Jan 29 - Mon, Feb 2
United Airlines Logo
6:00 am - 7:43 am
BTV
-
ORD
2h 43mnonstop
United Airlines Logo
3:50 pm - 10:54 pm
ORD
-
BTV
6h 04m1 stop
$219United Airlines
Thu, Feb 12 - Sun, Feb 15
United Airlines Logo
4:48 pm - 6:27 pm
BTV
-
ORD
2h 39mnonstop
United Airlines Logo
6:30 pm - 9:45 pm
ORD
-
BTV
2h 15mnonstop
$220United Airlines
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
7:30 am - 9:00 am
BDL
-
MDW
2h 30mnonstop
Southwest Logo
3:45 pm - 11:40 pm
MDW
-
BDL
6h 55m1 stop
$224Southwest
Wed, Apr 1 - Mon, Apr 6
American Airlines Logo
6:10 pm - 8:00 pm
BTV
-
ORD
2h 50mnonstop
American Airlines Logo
6:43 pm - 10:07 pm
ORD
-
BTV
2h 24mnonstop
$247American Airlines
Fri, May 15 - Mon, May 18

United Airlines flights from Vermont to Chicago

Our best United Airlines deals on Vermont to Chicago flight tickets
United Airlines
Feb 12
BTV6:00 amBurlington
2h 43m
ORD7:43 amChicago O'Hare Intl
Feb 15
ORD3:50 pmChicago O'Hare Intl
6h 04m
1 stop
BTV10:54 pmBurlington
$219
United Airlines
Jun 18
BTV4:48 pmBurlington
2h 39m
ORD6:27 pmChicago O'Hare Intl
Jun 23
ORD6:30 pmChicago O'Hare Intl
2h 15m
BTV9:45 pmBurlington
$220
United Airlines
May 13
BTV6:20 amBurlington
2h 39m
ORD7:59 amChicago O'Hare Intl
May 18
ORD6:30 pmChicago O'Hare Intl
2h 15m
BTV9:45 pmBurlington
$229

JetBlue flights from Vermont to Chicago

Our best JetBlue deals on Vermont to Chicago flight tickets
JetBlue
Feb 3
BDL6:00 amHartford Bradley Intl
14h 36m
1 stop
ORD7:36 pmChicago O'Hare Intl
Feb 5
ORD9:40 amChicago O'Hare Intl
13h 03m
1 stop
BDL11:43 pmHartford Bradley Intl
$267
JetBlue
Feb 5
BDL6:00 amHartford Bradley Intl
14h 31m
1 stop
ORD7:31 pmChicago O'Hare Intl
Feb 6
ORD9:15 amChicago O'Hare Intl
13h 28m
1 stop
BDL11:43 pmHartford Bradley Intl
$276
JetBlue
Feb 5
BDL6:00 amHartford Bradley Intl
12h 43m
2 stops
ORD5:43 pmChicago O'Hare Intl
Feb 6
ORD7:45 amChicago O'Hare Intl
14h 58m
2 stops
BDL11:43 pmHartford Bradley Intl
$280

momondo 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, momondo users made 832,500 searches. Data last updated January 11, 2026.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/23

10:52 am-8:27 pm

1 stop10h 35m

Chicago Midway

Thu 2/26

7:30 am-5:05 pm

1 stop8h 35m

$170

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 2/26

2:27 pm-10:39 pm

1 stop9h 12m

Chicago O'Hare Intl

Sun 3/1

5:05 am-1:32 pm

1 stop7h 27m

$170

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 1/23

1:56 pm-5:52 pm

2 stops28h 56m

Chicago O'Hare Intl

Wed 2/4

12:44 pm-7:36 pm

1 stop29h 52m

$197

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Wed 4/8

6:10 pm-8:00 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sat 4/11

2:04 pm-5:25 pm

Nonstop2h 21m

$209

AlbanyChicago

ALB - ORD

ALBORD

Albany Intl

Mon 2/2

10:00 am-9:12 am

2 stops24h 12m

Chicago O'Hare Intl

Wed 2/4

12:44 pm-8:46 am

1 stop19h 02m

$210

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/29

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Mon 2/2

1:25 pm-4:20 pm

Nonstop1h 55m

$215

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 2/12

6:00 am-7:43 am

Nonstop2h 43m

Chicago O'Hare Intl

Sun 2/15

3:50 pm-10:54 pm

1 stop6h 04m

$219

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Thu 6/18

4:48 pm-6:27 pm

Nonstop2h 39m

Chicago O'Hare Intl

Tue 6/23

6:30 pm-9:45 pm

Nonstop2h 15m

$220

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 4/1

7:30 am-9:00 am

Nonstop2h 30m

Chicago Midway

Mon 4/6

3:45 pm-11:40 pm

1 stop6h 55m

$224

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Fri 5/15

6:10 pm-8:00 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 5/18

6:43 pm-10:07 pm

Nonstop2h 24m

$247

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $290.

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 Friday when prices can be found for as low as $441. 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 $647.

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 afternoon. Flights from Vermont to Chicago during this time can be as low as $442. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $497.

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 $362 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 35% 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

$288

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Vermont in the past 72 hours is $288. The best round-trip flight deal from Vermont to Chicago found on momondo in the last 72 hours is $356.
The fastest flight from Vermont to Chicago takes 2h 10m
Direct flights go from Vermont to Chicago every day.
There are 3 airports in Chicago. From Vermont there are direct flights to 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?

  • 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?

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 AirlinesPriceFrom $209Free CancellationRating
7.2
11,106 reviews
Search American Airlines flights
United AirlinesPriceFrom $228Free CancellationRating
7.4
9,143 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
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

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport