Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Vermont to Chicago from $79

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 9/16. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Vermont to Chicago

Cheap round-trip flights

Frontier Logo
8:37 pm - 7:23 amBDL-MDW
11h 46m1 stop
Frontier Logo
10:13 am - 7:52 pmMDW-BDL
8h 39m1 stop
$171Frontier
Find Deal
dom., sep. 14 - dom., sep. 21
Frontier Logo
8:37 pm - 7:44 pmBDL-ORD
24h 07m1 stop
Frontier Logo
8:49 pm - 7:44 pmORD-BDL
21h 55m1 stop
$171Frontier
Find Deal
dom., sep. 7 - jue., sep. 11
Logo
4:01 pm - 11:39 pmBDL-ORD
8h 38m1 stop
Logo
1:26 pm - 10:22 amORD-BDL
19h 56m1 stop
$178
Find Deal
vie., oct. 24 - dom., oct. 26
Southwest Logo
5:25 am - 6:50 amBDL-MDW
2h 25mnonstop
Southwest Logo
8:20 pm - 11:20 pmMDW-BDL
2h 00mnonstop
$182Southwest
Find Deal
jue., oct. 23 - dom., oct. 26
United Airlines Logo
6:38 pm - 8:21 pmBDL-ORD
2h 43mnonstop
United Airlines Logo
11:15 am - 2:33 pmORD-BDL
2h 18mnonstop
$185United Airlines
Find Deal
jue., sep. 25 - dom., sep. 28
United Airlines Logo
6:00 am - 7:43 amBDL-ORD
2h 43mnonstop
United Airlines Logo
7:32 am - 10:51 amORD-BDL
2h 19mnonstop
$188United Airlines
Find Deal
mar., oct. 14 - jue., oct. 16
Logo
11:27 am - 11:44 pmBDL-ORD
13h 17m1 stop
Logo
12:53 pm - 10:22 amORD-BDL
20h 29m1 stop
$190
Find Deal
lun., oct. 20 - jue., oct. 23
Southwest Logo
5:20 pm - 6:40 pmBDL-MDW
2h 20mnonstop
Southwest Logo
7:25 am - 1:10 pmMDW-BDL
4h 45m1 stop
$192Southwest
Find Deal
mar., sep. 23 - mar., sep. 30
Delta Logo
2:36 pm - 9:36 pmBDL-MDW
8h 00m1 stop
Delta Logo
10:35 am - 5:43 pmMDW-BDL
6h 08m1 stop
$197Delta
Find Deal
mar., sep. 23 - mar., sep. 30
Delta Logo
11:28 am - 4:47 pmBDL-ORD
6h 19m1 stop
Delta Logo
1:05 pm - 8:27 pmORD-BDL
6h 22m1 stop
$197Delta
Find Deal
mar., sep. 23 - mar., sep. 30

United Airlines flights from Vermont to Chicago

Our best United Airlines deals on Vermont to Chicago flight tickets
United Airlines
Sep 25
BDL6:38 pmHartford Bradley Intl
2h 43m
ORD8:21 pmChicago O'Hare Intl
Sep 28
ORD11:15 amChicago O'Hare Intl
2h 18m
BDL2:33 pmHartford Bradley Intl
$185
Find similar
United Airlines
Oct 14
BDL6:00 amHartford Bradley Intl
2h 43m
ORD7:43 amChicago O'Hare Intl
Oct 16
ORD7:32 amChicago O'Hare Intl
2h 19m
BDL10:51 amHartford Bradley Intl
$188
Find similar
United Airlines
Sep 11
BDL6:10 amHartford Bradley Intl
2h 43m
ORD7:53 amChicago O'Hare Intl
Sep 16
ORD1:55 pmChicago O'Hare Intl
2h 28m
BDL5:23 pmHartford Bradley Intl
$192
Find similar

American Airlines flights from Vermont to Chicago

Our best American Airlines deals on Vermont to Chicago flight tickets
American Airlines
Oct 11
BDL5:44 pmHartford Bradley Intl
2h 45m
ORD7:29 pmChicago O'Hare Intl
Oct 14
ORD8:44 pmChicago O'Hare Intl
2h 24m
BDL12:08 amHartford Bradley Intl
$205
Find similar
American Airlines
Oct 11
BDL1:52 pmHartford Bradley Intl
6h 19m
1 stop
ORD7:11 pmChicago O'Hare Intl
Oct 14
ORD8:44 pmChicago O'Hare Intl
2h 24m
BDL12:08 amHartford Bradley Intl
$215
Find similar
American Airlines
Sep 18
BTV5:39 pmBurlington
2h 39m
ORD7:18 pmChicago O'Hare Intl
Sep 20
ORD6:10 amChicago O'Hare Intl
6h 52m
1 stop
BTV2:02 pmBurlington
$230
Find similar

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 agosto 27, 2025.
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

dom. 9/14

8:37 pm-7:23 am

1 stop11h 46m

Chicago Midway

dom. 9/21

10:13 am-7:52 pm

1 stop8h 39m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

dom. 9/7

8:37 pm-7:44 pm

1 stop24h 07m

Chicago O'Hare Intl

jue. 9/11

8:49 pm-7:44 pm

1 stop21h 55m

$171

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

vie. 10/24

4:01 pm-11:39 pm

1 stop8h 38m

Chicago O'Hare Intl

dom. 10/26

1:26 pm-10:22 am

1 stop19h 56m

$178

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jue. 10/23

5:25 am-6:50 am

Nonstop2h 25m

Chicago Midway

dom. 10/26

8:20 pm-11:20 pm

Nonstop2h 00m

$182

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

jue. 9/25

6:38 pm-8:21 pm

Nonstop2h 43m

Chicago O'Hare Intl

dom. 9/28

11:15 am-2:33 pm

Nonstop2h 18m

$185

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

mar. 10/14

6:00 am-7:43 am

Nonstop2h 43m

Chicago O'Hare Intl

jue. 10/16

7:32 am-10:51 am

Nonstop2h 19m

$188

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

lun. 10/20

11:27 am-11:44 pm

1 stop13h 17m

Chicago O'Hare Intl

jue. 10/23

12:53 pm-10:22 am

1 stop20h 29m

$190

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mar. 9/23

5:20 pm-6:40 pm

Nonstop2h 20m

Chicago Midway

mar. 9/30

7:25 am-1:10 pm

1 stop4h 45m

$192

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mar. 9/23

2:36 pm-9:36 pm

1 stop8h 00m

Chicago Midway

mar. 9/30

10:35 am-5:43 pm

1 stop6h 08m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

mar. 9/23

11:28 am-4:47 pm

1 stop6h 19m

Chicago O'Hare Intl

mar. 9/30

1:05 pm-8:27 pm

1 stop6h 22m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 May is, on average, the cheapest month to fly to Chicago from Vermont, with most prices found around $294. If you’re not able to fly to Chicago in May, then January is your next best option. Flight prices from Vermont to Chicago during January average around $316.

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 Thursday when prices can be found for as low as $451. 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 $643.

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 $522.

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 $353 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 $294 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?

No. A direct flight is the cheapest option for a flight between Vermont 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

$242

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Vermont in the past 72 hours is $242. The best round-trip flight deal from Vermont to Chicago found on momondo in the last 72 hours is $352.
The fastest flight from Vermont to Chicago takes 2h 05m
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?

  • 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
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $253Free CancellationRating
7.4
8,945 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
Lansing
Portage
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.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
lun. 9/1
lun. 9/8
By creating a price alert you accept our terms of use and privacy policy.

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