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Cheap flights from Vermont to Chicago from $60

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 2/18. 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
2:27 pm - 10:29 pm
BDL
-
MDW
9h 02m1 stop
Frontier Logo
9:22 pm - 9:23 am
MDW
-
BDL
11h 01m1 stop
$160Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
6:17 pm - 2:55 pm
BDL
-
MDW
21h 38m1 stop
Frontier Logo
9:22 pm - 8:53 am
MDW
-
BDL
10h 31m1 stop
$174Frontier
Fri, Feb 20 - Mon, Feb 23
Frontier Logo
2:27 pm - 10:37 pm
BDL
-
MDW
9h 10m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$181Frontier
Thu, Feb 19 - Thu, Feb 26
Multiple Airlines Logo
7:00 am - 7:58 pm
BDL
-
MDW
13h 58m2 stops
Multiple Airlines Logo
7:00 pm - 11:24 am
MDW
-
BDL
15h 24m1 stop
$188Multiple Airlines
Mon, Feb 2 - Mon, Feb 9
Frontier Logo
12:11 pm - 10:19 pm
BDL
-
MDW
11h 08m1 stop
Frontier Logo
8:00 am - 8:15 pm
MDW
-
BDL
11h 15m1 stop
$195Frontier
Sun, Feb 8 - Sat, Feb 14
Southwest Logo
5:30 am - 6:55 am
ALB
-
MDW
2h 25mnonstop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$198Southwest
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
9:00 am - 2:55 pm
ALB
-
MDW
6h 55m1 stop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$208Southwest
Tue, Mar 3 - Wed, Mar 4
Delta Logo
12:51 pm - 5:29 pm
ALB
-
MDW
5h 38m1 stop
Delta Logo
6:00 am - 11:55 am
MDW
-
ALB
4h 55m1 stop
$217Delta
Thu, Jan 29 - Wed, Feb 11
Multiple Airlines Logo
7:00 am - 7:52 pm
BDL
-
MDW
13h 52m2 stops
Multiple Airlines Logo
7:00 pm - 11:24 am
MDW
-
BDL
15h 24m1 stop
$219Multiple Airlines
Fri, Feb 6 - Mon, Feb 9
Delta Logo
5:23 am - 11:59 am
BTV
-
MDW
7h 36m1 stop
Delta Logo
6:35 pm - 11:27 pm
MDW
-
BTV
3h 52m1 stop
$229Delta
Wed, Jan 28 - Mon, Feb 9

Frontier flights from Vermont to Chicago Midway Airport

Our best Frontier deals on Vermont to Chicago Midway Airport flight tickets
Frontier
Feb 26
BDL2:27 pmHartford Bradley Intl
9h 02m
1 stop
MDW10:29 pmChicago Midway
Mar 2
MDW9:22 pmChicago Midway
11h 01m
1 stop
BDL9:23 amHartford Bradley Intl
$160
Find similar
Frontier
Feb 20
BDL6:17 pmHartford Bradley Intl
21h 38m
1 stop
MDW2:55 pmChicago Midway
Feb 23
MDW9:22 pmChicago Midway
10h 31m
1 stop
BDL8:53 amHartford Bradley Intl
$174
Find similar
Frontier
Feb 19
BDL2:27 pmHartford Bradley Intl
9h 10m
1 stop
MDW10:37 pmChicago Midway
Feb 26
MDW7:30 amChicago Midway
8h 35m
1 stop
BDL5:05 pmHartford Bradley Intl
$181
Find similar

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
Jan 29
ALB12:51 pmAlbany Intl
5h 38m
1 stop
MDW5:29 pmChicago Midway
Feb 11
MDW6:00 amChicago Midway
4h 55m
1 stop
ALB11:55 amAlbany Intl
$217
Find similar
Delta
May 2
BTV7:10 amBurlington
6h 20m
1 stop
MDW12:30 pmChicago Midway
May 4
MDW6:34 pmChicago Midway
3h 32m
1 stop
BTV11:06 pmBurlington
$229
Find similar
Delta
Feb 3
BDL7:20 amHartford Bradley Intl
5h 39m
1 stop
MDW11:59 amChicago Midway
Feb 10
MDW9:33 amChicago Midway
5h 35m
1 stop
BDL4:08 pmHartford Bradley Intl
$233
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Vermont to Chicago Midway Airport 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 7, 2026.
Use the filters below to find and compare flights from Vermont to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 2/26

2:27 pm-10:29 pm

1 stop9h 02m

Chicago Midway

Mon 3/2

9:22 pm-9:23 am

1 stop11h 01m

$160

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 2/20

6:17 pm-2:55 pm

1 stop21h 38m

Chicago Midway

Mon 2/23

9:22 pm-8:53 am

1 stop10h 31m

$174

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 2/19

2:27 pm-10:37 pm

1 stop9h 10m

Chicago Midway

Thu 2/26

7:30 am-5:05 pm

1 stop8h 35m

$181

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/2

7:00 am-7:58 pm

2 stops13h 58m

Chicago Midway

Mon 2/9

7:00 pm-11:24 am

1 stop15h 24m

$188

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 2/8

12:11 pm-10:19 pm

1 stop11h 08m

Chicago Midway

Sat 2/14

8:00 am-8:15 pm

1 stop11h 15m

$195

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 3/3

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Wed 3/4

1:25 pm-4:15 pm

Nonstop1h 50m

$198

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 3/3

9:00 am-2:55 pm

1 stop6h 55m

Chicago Midway

Wed 3/4

1:25 pm-4:15 pm

Nonstop1h 50m

$208

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 1/29

12:51 pm-5:29 pm

1 stop5h 38m

Chicago Midway

Wed 2/11

6:00 am-11:55 am

1 stop4h 55m

$217

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 2/6

7:00 am-7:52 pm

2 stops13h 52m

Chicago Midway

Mon 2/9

7:00 pm-11:24 am

1 stop15h 24m

$219

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 1/28

5:23 am-11:59 am

1 stop7h 36m

Chicago Midway

Mon 2/9

6:35 pm-11:27 pm

1 stop3h 52m

$229

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 Midway Airport

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 airline that flies from Vermont to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Vermont to Chicago Midway

Cheap Vermont to Chicago Midway Airport flight deals and tips

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

Fastest flight time

2h 10m

Direct flights

Every day
The fastest flight from Vermont to Chicago Midway Airport takes 2h 10m
Direct flights go from Vermont to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Vermont to Chicago Midway Airport are refreshed on a daily basis.

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

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

    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 Vermont to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Vermont to Chicago for you.

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 offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight 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?

Of course. momondo tracks the price of Vermont to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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