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Cheap flights from Vermont to Chicago from $70

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.
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Cheap round-trip flights

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Southwest Logo
5:10 am - 6:45 amBDL-MDW
2h 35mnonstop
Southwest Logo
6:05 pm - 9:05 pmMDW-BDL
2h 00mnonstop
$225Southwest
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Sun, Feb 22 - Sat, Feb 28
Southwest Logo
7:25 am - 1:00 pmBDL-MDW
6h 35m2 stops
Southwest Logo
12:55 pm - 8:05 pmMDW-BDL
6h 10m1 stop
$227Southwest
Find Deal
Thu, Dec 11 - Tue, Dec 16
Frontier Logo
12:05 pm - 5:38 pmBDL-MDW
6h 33m1 stop
Frontier Logo
6:15 am - 3:29 pmMDW-BDL
8h 14m1 stop
$228Frontier
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Thu, Dec 18 - Mon, Dec 22
Southwest Logo
6:00 am - 1:00 pmBDL-MDW
8h 00m2 stops
Southwest Logo
12:25 pm - 10:05 pmMDW-BDL
8h 40m2 stops
$232Southwest
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Thu, Dec 11 - Tue, Dec 16
Multiple Airlines Logo
5:42 pm - 4:57 pmBDL-MDW
24h 15m1 stop
Multiple Airlines Logo
7:44 am - 1:42 pmMDW-BDL
28h 58m2 stops
$234Multiple Airlines
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Tue, Nov 25 - Tue, Dec 2
Southwest Logo
5:30 am - 7:05 amBDL-MDW
2h 35mnonstop
Southwest Logo
6:40 am - 11:55 amMDW-BDL
4h 15m1 stop
$235Southwest
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Thu, Jan 8 - Sat, Jan 10
Southwest Logo
7:10 pm - 8:45 pmBDL-MDW
2h 35mnonstop
Southwest Logo
5:40 am - 3:40 pmMDW-BDL
9h 00m2 stops
$240Southwest
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Sun, Feb 22 - Sat, Feb 28
Delta Logo
5:30 am - 8:54 amBDL-MDW
4h 24m1 stop
Delta Logo
12:46 pm - 9:32 pmMDW-BDL
7h 46m1 stop
$245Delta
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
6:00 am - 8:54 amALB-MDW
3h 54m1 stop
Delta Logo
6:00 am - 1:13 pmMDW-ALB
6h 13m1 stop
$251Delta
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Mon, Nov 24 - Thu, Nov 27
Multiple Airlines Logo
9:59 am - 9:58 pmALB-MDW
12h 59m1 stop
Multiple Airlines Logo
10:13 am - 9:32 amMDW-ALB
22h 19m1 stop
$266Multiple Airlines
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Thu, Dec 11 - Thu, Dec 18

Southwest flights from Vermont to Chicago Midway Airport

Our best Southwest deals on Vermont to Chicago Midway Airport flight tickets
Southwest
Feb 22
BDL5:10 amHartford Bradley Intl
2h 35m
MDW6:45 amChicago Midway
Feb 28
MDW6:05 pmChicago Midway
2h 00m
BDL9:05 pmHartford Bradley Intl
$225
Find similar
Southwest
Dec 11
BDL7:25 amHartford Bradley Intl
6h 35m
2 stops
MDW1:00 pmChicago Midway
Dec 16
MDW12:55 pmChicago Midway
6h 10m
1 stop
BDL8:05 pmHartford Bradley Intl
$227
Find similar
Southwest
Dec 11
BDL6:00 amHartford Bradley Intl
8h 00m
2 stops
MDW1:00 pmChicago Midway
Dec 16
MDW12:25 pmChicago Midway
8h 40m
2 stops
BDL10:05 pmHartford Bradley Intl
$232
Find similar

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
Nov 24
BDL12:10 pmHartford Bradley Intl
5h 29m
1 stop
MDW4:39 pmChicago Midway
Dec 2
MDW6:40 pmChicago Midway
3h 58m
1 stop
BDL11:38 pmHartford Bradley Intl
$245
Find similar
Delta
Nov 24
ALB6:00 amAlbany Intl
3h 54m
1 stop
MDW8:54 amChicago Midway
Nov 27
MDW6:00 amChicago Midway
6h 13m
1 stop
ALB1:13 pmAlbany Intl
$251
Find similar
Delta
Jan 12
BDL5:35 pmHartford Bradley Intl
5h 34m
1 stop
MDW10:09 pmChicago Midway
Jan 16
MDW6:30 pmChicago Midway
4h 10m
1 stop
BDL11:40 pmHartford Bradley Intl
$258
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 November 13, 2025.
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

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 - 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 - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/11

6:00 am-1:00 pm

2 stops8h 00m

Chicago Midway

Tue 12/16

12:25 pm-10:05 pm

2 stops8h 40m

$232

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 11/25

5:42 pm-4:57 pm

1 stop24h 15m

Chicago Midway

Tue 12/2

7:44 am-1:42 pm

2 stops28h 58m

$234

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/8

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Sat 1/10

6:40 am-11:55 am

1 stop4h 15m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 2/22

7:10 pm-8:45 pm

Nonstop2h 35m

Chicago Midway

Sat 2/28

5:40 am-3:40 pm

2 stops9h 00m

$240

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

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Mon 11/24

6:00 am-8:54 am

1 stop3h 54m

Chicago Midway

Thu 11/27

6:00 am-1:13 pm

1 stop6h 13m

$251

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 12/11

9:59 am-9:58 pm

1 stop12h 59m

Chicago Midway

Thu 12/18

10:13 am-9:32 am

1 stop22h 19m

$266

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?

Frontier, 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.
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  • 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
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?

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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