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Cheap flights from Vermont to Chicago from $99

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 10/21. 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

Frontier Logo
10:04 am - 8:21 pmBDL-MDW
11h 17m1 stop
Frontier Logo
6:15 am - 3:06 pmMDW-BDL
7h 51m1 stop
$188Frontier
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Thu, Oct 23 - Mon, Oct 27
Delta Logo
5:30 am - 8:54 amBDL-MDW
4h 24m1 stop
Delta Logo
6:48 pm - 11:22 pmMDW-BDL
3h 34m1 stop
$197Delta
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Thu, Nov 13 - Sun, Nov 16
Frontier Logo
4:20 pm - 11:46 pmBDL-MDW
8h 26m1 stop
Frontier Logo
12:09 pm - 10:46 amMDW-BDL
21h 37m1 stop
$200Frontier
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Fri, Oct 17 - Sun, Oct 19
Frontier Logo
10:04 am - 8:21 pmBDL-MDW
11h 17m1 stop
Frontier Logo
6:15 am - 9:09 amMDW-BDL
25h 54m1 stop
$210Frontier
Find Deal
Thu, Oct 16 - Sat, Oct 18
Frontier Logo
7:36 pm - 9:22 pmBDL-MDW
26h 46m1 stop
Frontier Logo
10:12 am - 2:12 pmMDW-BDL
27h 00m1 stop
$211Frontier
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Fri, Nov 14 - Sun, Nov 16
Frontier Logo
7:36 pm - 9:22 pmBDL-MDW
26h 46m1 stop
Frontier Logo
10:12 am - 2:12 pmMDW-BDL
27h 00m1 stop
$213Frontier
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Fri, Nov 14 - Sun, Nov 16
Southwest Logo
5:15 am - 6:45 amBDL-MDW
2h 30mnonstop
Southwest Logo
11:55 am - 2:55 pmMDW-BDL
2h 00mnonstop
$225Southwest
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Wed, Nov 12 - Sun, Nov 16
Multiple Airlines Logo
8:05 am - 9:12 amBDL-MDW
26h 07m1 stop
Multiple Airlines Logo
9:32 am - 9:48 pmMDW-BDL
11h 16m2 stops
$226Multiple Airlines
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Wed, Oct 29 - Fri, Oct 31
Southwest Logo
5:15 am - 6:45 amBDL-MDW
2h 30mnonstop
Southwest Logo
11:55 am - 2:55 pmMDW-BDL
2h 00mnonstop
$227Southwest
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Thu, Nov 13 - Sun, Nov 16
Multiple Airlines Logo
8:31 pm - 9:33 amBDL-MDW
14h 02m1 stop
Multiple Airlines Logo
9:45 am - 12:13 pmMDW-BDL
25h 28m2 stops
$228Multiple Airlines
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Thu, Oct 16 - Mon, Oct 20

Southwest flights from Vermont to Chicago Midway Airport

Our best Southwest deals on Vermont to Chicago Midway Airport flight tickets
Southwest
Nov 12
BDL5:15 amHartford Bradley Intl
2h 30m
MDW6:45 amChicago Midway
Nov 16
MDW11:55 amChicago Midway
2h 00m
BDL2:55 pmHartford Bradley Intl
$225
Find similar
Southwest
Nov 13
BDL5:15 amHartford Bradley Intl
2h 30m
MDW6:45 amChicago Midway
Nov 16
MDW11:55 amChicago Midway
2h 00m
BDL2:55 pmHartford Bradley Intl
$227
Find similar
Southwest
Oct 31
BDL4:40 pmHartford Bradley Intl
2h 30m
MDW6:10 pmChicago Midway
Nov 2
MDW5:05 amChicago Midway
5h 40m
1 stop
BDL11:45 amHartford Bradley Intl
$235
Find similar

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
Nov 13
BDL5:30 amHartford Bradley Intl
4h 24m
1 stop
MDW8:54 amChicago Midway
Nov 16
MDW6:48 pmChicago Midway
3h 34m
1 stop
BDL11:22 pmHartford Bradley Intl
$197
Find similar
Delta
Oct 23
BTV7:14 amBurlington
6h 14m
1 stop
MDW12:28 pmChicago Midway
Oct 25
MDW11:10 amChicago Midway
4h 25m
1 stop
BTV4:35 pmBurlington
$229
Find similar
Delta
Oct 23
BTV7:14 amBurlington
6h 14m
1 stop
MDW12:28 pmChicago Midway
Oct 28
MDW1:08 pmChicago Midway
8h 30m
2 stops
BTV10:38 pmBurlington
$234
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 September 24, 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

Thu 10/23

10:04 am-8:21 pm

1 stop11h 17m

Chicago Midway

Mon 10/27

6:15 am-3:06 pm

1 stop7h 51m

$188

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/13

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Sun 11/16

6:48 pm-11:22 pm

1 stop3h 34m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 10/17

4:20 pm-11:46 pm

1 stop8h 26m

Chicago Midway

Sun 10/19

12:09 pm-10:46 am

1 stop21h 37m

$200

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/16

10:04 am-8:21 pm

1 stop11h 17m

Chicago Midway

Sat 10/18

6:15 am-9:09 am

1 stop25h 54m

$210

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 11/14

7:36 pm-9:22 pm

1 stop26h 46m

Chicago Midway

Sun 11/16

10:12 am-2:12 pm

1 stop27h 00m

$211

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 11/14

7:36 pm-9:22 pm

1 stop26h 46m

Chicago Midway

Sun 11/16

10:12 am-2:12 pm

1 stop27h 00m

$213

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 11/12

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sun 11/16

11:55 am-2:55 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 10/29

8:05 am-9:12 am

1 stop26h 07m

Chicago Midway

Fri 10/31

9:32 am-9:48 pm

2 stops11h 16m

$226

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/13

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sun 11/16

11:55 am-2:55 pm

Nonstop2h 00m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/16

8:31 pm-9:33 am

1 stop14h 02m

Chicago Midway

Mon 10/20

9:45 am-12:13 pm

2 stops25h 28m

$228

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?

Delta, Frontier, and Southwest 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
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?

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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