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Cheap flights from Vermont to Chicago from $145

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 7/1. 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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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.
Delta Logo
1:20 pm - 6:31 pm
BTV
-
MDW
6h 11m
1 stop
Delta Logo
6:00 am - 1:46 pm
MDW
-
BTV
6h 46m
1 stop
$288Delta
Wed, Jun 24 - Tue, Jun 30
Delta Logo
1:20 pm - 6:31 pm
BTV
-
MDW
6h 11m
1 stop
Delta Logo
9:17 am - 4:11 pm
MDW
-
BTV
5h 54m
1 stop
$289Delta
Fri, Jun 12 - Sun, Jun 14
Delta Logo
1:20 pm - 6:31 pm
BTV
-
MDW
6h 11m
1 stop
Delta Logo
1:26 pm - 11:27 pm
MDW
-
BTV
9h 01m
2 stops
$293Delta
Wed, Jun 24 - Tue, Jun 30
Delta Logo
12:09 pm - 10:36 pm
BTV
-
MDW
11h 27m
2 stops
Delta Logo
6:42 pm - 11:25 pm
MDW
-
BTV
3h 43m
1 stop
$294Delta
Wed, Aug 12 - Sat, Aug 15
Delta Logo
6:59 am - 6:01 pm
BTV
-
MDW
12h 02m
2 stops
Delta Logo
1:27 pm - 10:31 pm
MDW
-
BTV
8h 04m
2 stops
$300Delta
Wed, Aug 12 - Sat, Aug 15
Delta Logo
7:19 am - 12:46 pm
BTV
-
MDW
6h 27m
1 stop
Delta Logo
5:47 pm - 11:14 pm
MDW
-
BTV
4h 27m
1 stop
$308Delta
Thu, Jun 25 - Sat, Jun 27
Delta Logo
1:20 pm - 6:31 pm
BTV
-
MDW
6h 11m
1 stop
Delta Logo
9:17 am - 4:11 pm
MDW
-
BTV
5h 54m
1 stop
$309Delta
Thu, Jun 11 - Thu, Jun 18
Delta Logo
12:20 pm - 10:17 pm
BTV
-
MDW
10h 57m
2 stops
Delta Logo
5:47 pm - 11:14 pm
MDW
-
BTV
4h 27m
1 stop
$314Delta
Tue, Jun 23 - Sat, Jun 27
Southwest Logo
6:05 pm - 7:15 pm
ALB
-
MDW
2h 10mnonstop
Southwest Logo
7:45 am - 10:45 am
MDW
-
ALB
2h 00mnonstop
$319Southwest
Thu, Sep 3 - Sat, Sep 5
Southwest Logo
7:50 am - 9:00 am
ALB
-
MDW
2h 10mnonstop
Southwest Logo
9:10 am - 1:50 pm
MDW
-
ALB
3h 40m
1 stop
$325Southwest
Wed, Oct 7 - Sat, Oct 10

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
Jun 24
BTV1:20 pmBurlington
6h 11m
1 stop
MDW6:31 pmChicago Midway
Jun 30
MDW6:00 amChicago Midway
6h 46m
1 stop
BTV1:46 pmBurlington
$288
Delta
Jun 12
BTV1:20 pmBurlington
6h 11m
1 stop
MDW6:31 pmChicago Midway
Jun 14
MDW9:17 amChicago Midway
5h 54m
1 stop
BTV4:11 pmBurlington
$289
Delta
Jun 24
BTV1:20 pmBurlington
6h 11m
1 stop
MDW6:31 pmChicago Midway
Jun 30
MDW1:26 pmChicago Midway
9h 01m
2 stops
BTV11:27 pmBurlington
$293

Southwest flights from Vermont to Chicago Midway Airport

Our best Southwest deals on Vermont to Chicago Midway Airport flight tickets
Southwest
Sep 3
ALB6:05 pmAlbany Intl
2h 10m
MDW7:15 pmChicago Midway
Sep 5
MDW7:45 amChicago Midway
2h 00m
ALB10:45 amAlbany Intl
$319
Southwest
Oct 7
ALB7:50 amAlbany Intl
2h 10m
MDW9:00 amChicago Midway
Oct 10
MDW9:10 amChicago Midway
3h 40m
1 stop
ALB1:50 pmAlbany Intl
$325
Southwest
Jul 24
ALB7:15 pmAlbany Intl
2h 15m
MDW8:30 pmChicago Midway
Jul 28
MDW7:45 amChicago Midway
2h 00m
ALB10:45 amAlbany Intl
$327

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 May 25, 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

Cheapest round-trip

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 6/24

1:20 pm-6:31 pm

1 stop6h 11m

Chicago Midway

Tue 6/30

6:00 am-1:46 pm

1 stop6h 46m

$288

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Fri 6/12

1:20 pm-6:31 pm

1 stop6h 11m

Chicago Midway

Sun 6/14

9:17 am-4:11 pm

1 stop5h 54m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 6/24

1:20 pm-6:31 pm

1 stop6h 11m

Chicago Midway

Tue 6/30

1:26 pm-11:27 pm

2 stops9h 01m

$293

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 8/12

12:09 pm-10:36 pm

2 stops11h 27m

Chicago Midway

Sat 8/15

6:42 pm-11:25 pm

1 stop3h 43m

$294

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Wed 8/12

6:59 am-6:01 pm

2 stops12h 02m

Chicago Midway

Sat 8/15

1:27 pm-10:31 pm

2 stops8h 04m

$300

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 6/25

7:19 am-12:46 pm

1 stop6h 27m

Chicago Midway

Sat 6/27

5:47 pm-11:14 pm

1 stop4h 27m

$308

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Thu 6/11

1:20 pm-6:31 pm

1 stop6h 11m

Chicago Midway

Thu 6/18

9:17 am-4:11 pm

1 stop5h 54m

$309

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Tue 6/23

12:20 pm-10:17 pm

2 stops10h 57m

Chicago Midway

Sat 6/27

5:47 pm-11:14 pm

1 stop4h 27m

$314
Quickest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 9/3

6:05 pm-7:15 pm

Nonstop2h 10m

Chicago Midway

Sat 9/5

7:45 am-10:45 am

Nonstop2h 00m

$319

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 10/7

7:50 am-9:00 am

Nonstop2h 10m

Chicago Midway

Sat 10/10

9:10 am-1:50 pm

1 stop3h 40m

$325

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

Can stopping save me money on Vermont to Chicago Midway Airport flights?

You could potentially save up to 82% on your flight if you consider stops on a Vermont to Chicago Midway Airport flight.

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 05m

Direct flights

Every day
The fastest flight from Vermont to Chicago Midway Airport takes 2h 05m
Direct flights go from Vermont to Chicago Midway Airport every day.
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Frequently asked questions about flying from Vermont to Chicago Midway Airport

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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.

An easier way to manage your Chicago Midway Airport trip

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