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Cheap flights from Vermont to Chicago from $69

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 8/31. 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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Find the cheapest flights from Vermont to Chicago

Cheap round-trip flights

Southwest Logo
5:25 pm - 6:45 pmBDL-MDW
2h 20mnonstop
Southwest Logo
10:00 am - 1:10 pmMDW-BDL
2h 10mnonstop
$137Southwest
Find Deal
gio, set 25 - dom, set 28
Southwest Logo
5:45 am - 9:00 amBDL-MDW
4h 15m1 stop
Southwest Logo
10:00 am - 1:10 pmMDW-BDL
2h 10mnonstop
$147Southwest
Find Deal
gio, set 25 - dom, set 28
Southwest Logo
5:30 am - 6:50 amBDL-MDW
2h 20mnonstop
Southwest Logo
6:10 pm - 9:20 pmMDW-BDL
2h 10mnonstop
$177Southwest
Find Deal
lun, set 15 - mar, set 16
Southwest Logo
5:00 pm - 6:20 pmBDL-MDW
2h 20mnonstop
Southwest Logo
6:10 pm - 9:20 pmMDW-BDL
2h 10mnonstop
$187Southwest
Find Deal
sab, ago 23 - mar, ago 26
Delta Logo
7:00 am - 11:48 amBDL-MDW
5h 48m1 stop
Delta Logo
6:00 am - 1:36 pmMDW-BDL
6h 36m1 stop
$197Delta
Find Deal
gio, ago 21 - mar, ago 26
Delta Logo
7:20 am - 12:28 pmBTV-MDW
6h 08m1 stop
Delta Logo
4:25 pm - 10:42 pmMDW-BTV
5h 17m1 stop
$205Delta
Find Deal
mar, ago 26 - sab, ago 30
Delta Logo
6:00 am - 12:28 pmBTV-MDW
7h 28m2 stops
Delta Logo
4:25 pm - 10:42 pmMDW-BTV
5h 17m1 stop
$210Delta
Find Deal
mar, ago 26 - sab, ago 30
Frontier Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Frontier Logo
10:13 am - 7:52 pmMDW-BDL
8h 39m1 stop
$218Frontier
Find Deal
gio, set 11 - dom, set 14
Frontier Logo
8:39 pm - 9:51 amBDL-MDW
14h 12m1 stop
Frontier Logo
8:19 am - 7:57 pmMDW-BDL
10h 38m1 stop
$225Frontier
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ven, set 12 - lun, set 15
Frontier Logo
8:52 pm - 9:51 amBDL-MDW
13h 59m1 stop
Frontier Logo
8:19 am - 7:57 pmMDW-BDL
10h 38m1 stop
$233Frontier
Find Deal
ven, ott 3 - lun, ott 6

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
Aug 21
BDL7:00 amHartford Bradley Intl
5h 48m
1 stop
MDW11:48 amChicago Midway
Aug 26
MDW6:00 amChicago Midway
6h 36m
1 stop
BDL1:36 pmHartford Bradley Intl
$197
Find similar
Delta
Aug 26
BTV7:20 amBurlington
6h 08m
1 stop
MDW12:28 pmChicago Midway
Aug 30
MDW4:25 pmChicago Midway
5h 17m
1 stop
BTV10:42 pmBurlington
$205
Find similar
Delta
Aug 26
BTV6:00 amBurlington
7h 28m
2 stops
MDW12:28 pmChicago Midway
Aug 30
MDW4:25 pmChicago Midway
5h 17m
1 stop
BTV10:42 pmBurlington
$210
Find similar

Frontier flights from Vermont to Chicago Midway Airport

Our best Frontier deals on Vermont to Chicago Midway Airport flight tickets
Frontier
Sep 11
BDL10:30 amHartford Bradley Intl
6h 28m
1 stop
MDW3:58 pmChicago Midway
Sep 14
MDW10:13 amChicago Midway
8h 39m
1 stop
BDL7:52 pmHartford Bradley Intl
$218
Find similar
Frontier
Sep 12
BDL8:39 pmHartford Bradley Intl
14h 12m
1 stop
MDW9:51 amChicago Midway
Sep 15
MDW8:19 amChicago Midway
10h 38m
1 stop
BDL7:57 pmHartford Bradley Intl
$225
Find similar
Frontier
Oct 3
BDL8:52 pmHartford Bradley Intl
13h 59m
1 stop
MDW9:51 amChicago Midway
Oct 6
MDW8:19 amChicago Midway
10h 38m
1 stop
BDL7:57 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 agosto 2, 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

gio 9/25

5:25 pm-6:45 pm

Nonstop2h 20m

Chicago Midway

dom 9/28

10:00 am-1:10 pm

Nonstop2h 10m

$137

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

gio 9/25

5:45 am-9:00 am

1 stop4h 15m

Chicago Midway

dom 9/28

10:00 am-1:10 pm

Nonstop2h 10m

$147

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

lun 9/15

5:30 am-6:50 am

Nonstop2h 20m

Chicago Midway

mar 9/16

6:10 pm-9:20 pm

Nonstop2h 10m

$177

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

sab 8/23

5:00 pm-6:20 pm

Nonstop2h 20m

Chicago Midway

mar 8/26

6:10 pm-9:20 pm

Nonstop2h 10m

$187

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

gio 8/21

7:00 am-11:48 am

1 stop5h 48m

Chicago Midway

mar 8/26

6:00 am-1:36 pm

1 stop6h 36m

$197

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

mar 8/26

7:20 am-12:28 pm

1 stop6h 08m

Chicago Midway

sab 8/30

4:25 pm-10:42 pm

1 stop5h 17m

$205

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

mar 8/26

6:00 am-12:28 pm

2 stops7h 28m

Chicago Midway

sab 8/30

4:25 pm-10:42 pm

1 stop5h 17m

$210

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

gio 9/11

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

dom 9/14

10:13 am-7:52 pm

1 stop8h 39m

$218

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

ven 9/12

8:39 pm-9:51 am

1 stop14h 12m

Chicago Midway

lun 9/15

8:19 am-7:57 pm

1 stop10h 38m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

ven 10/3

8:52 pm-9:51 am

1 stop13h 59m

Chicago Midway

lun 10/6

8:19 am-7:57 pm

1 stop10h 38m

$233

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, Delta, and Frontier 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

Best Price Found

$69

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Vermont in the past 72 hours is $69. The best round-trip flight deal from Vermont to Chicago Midway Airport found on momondo in the last 72 hours is $137.
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
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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1 adult
gio 8/7
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