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Cheap flights from Chicago Midway Airport to Vermont from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Vermont departing on 12/5. 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 Chicago Midway Airport to Vermont

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:50 am - 2:55 pmMDW-BDL
5h 05m1 stop
Southwest Logo
7:15 pm - 8:45 pmBDL-MDW
2h 30mnonstop
$167Southwest
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Thu, Dec 4 - Sun, Dec 7
Delta Logo
4:30 pm - 10:34 pmMDW-BDL
5h 04m1 stop
Delta Logo
5:30 am - 8:54 amBDL-MDW
4h 24m1 stop
$177Delta
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Sat, Jan 31 - Sun, Feb 1
Southwest Logo
8:50 am - 2:55 pmMDW-BDL
5h 05m1 stop
Southwest Logo
2:00 pm - 8:30 pmBDL-MDW
7h 30m2 stops
$182Southwest
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Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
3:52 pm - 2:49 pmMDW-BDL
21h 57m1 stop
Multiple Airlines Logo
2:07 pm - 8:46 amBDL-MDW
19h 39m2 stops
$192Multiple Airlines
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Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
3:52 pm - 2:49 pmMDW-BDL
21h 57m1 stop
Multiple Airlines Logo
12:48 pm - 6:12 pmBDL-MDW
6h 24m1 stop
$195Multiple Airlines
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Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
3:52 pm - 2:49 pmMDW-BDL
21h 57m1 stop
Multiple Airlines Logo
12:48 pm - 6:12 pmBDL-MDW
6h 24m1 stop
$212Multiple Airlines
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Fri, Dec 12 - Sun, Dec 14
Multiple Airlines Logo
6:20 am - 7:32 pmMDW-BDL
12h 12m2 stops
Multiple Airlines Logo
11:59 am - 7:42 pmBDL-MDW
8h 43m1 stop
$219Multiple Airlines
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Thu, Nov 20 - Fri, Dec 5
Southwest Logo
8:50 am - 2:55 pmMDW-BDL
5h 05m1 stop
Southwest Logo
12:20 pm - 7:05 pmBDL-MDW
7h 45m2 stops
$227Southwest
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Thu, Dec 11 - Sun, Dec 14
Frontier Logo
2:59 pm - 11:30 amMDW-BDL
19h 31m2 stops
Frontier Logo
2:07 pm - 9:58 pmBDL-MDW
8h 51m1 stop
$244Frontier
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Sat, Dec 6 - Mon, Dec 8
Frontier Logo
5:47 pm - 7:32 pmMDW-BDL
24h 45m1 stop
Frontier Logo
8:27 pm - 5:15 pmBDL-MDW
21h 48m2 stops
$306Frontier
Find Deal
Mon, Nov 24 - Sun, Nov 30

Delta flights from Chicago Midway Airport to Vermont

Our best Delta deals on Chicago Midway Airport to Vermont flight tickets
Delta
Jan 31
MDW4:30 pmChicago Midway
5h 04m
1 stop
BDL10:34 pmHartford Bradley Intl
Feb 1
BDL5:30 amHartford Bradley Intl
4h 24m
1 stop
MDW8:54 amChicago Midway
$177
Find similar
Delta
Dec 4
MDW6:40 pmChicago Midway
3h 52m
1 stop
BTV11:32 pmBurlington
Dec 11
BTV7:05 amBurlington
6h 29m
1 stop
MDW12:34 pmChicago Midway
$229
Find similar
Delta
Mar 3
MDW9:34 amChicago Midway
5h 48m
1 stop
BDL4:22 pmHartford Bradley Intl
Mar 4
BDL5:30 amHartford Bradley Intl
4h 24m
1 stop
MDW8:54 amChicago Midway
$245
Find similar

Southwest flights from Chicago Midway Airport to Vermont

Our best Southwest deals on Chicago Midway Airport to Vermont flight tickets
Southwest
Dec 4
MDW8:50 amChicago Midway
5h 05m
1 stop
BDL2:55 pmHartford Bradley Intl
Dec 7
BDL7:15 pmHartford Bradley Intl
2h 30m
MDW8:45 pmChicago Midway
$167
Find similar
Southwest
Dec 4
MDW8:50 amChicago Midway
5h 05m
1 stop
BDL2:55 pmHartford Bradley Intl
Dec 7
BDL2:00 pmHartford Bradley Intl
7h 30m
2 stops
MDW8:30 pmChicago Midway
$182
Find similar
Southwest
Dec 11
MDW8:50 amChicago Midway
5h 05m
1 stop
BDL2:55 pmHartford Bradley Intl
Dec 14
BDL12:20 pmHartford Bradley Intl
7h 45m
2 stops
MDW7:05 pmChicago Midway
$227
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Vermont 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 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Vermont that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 12/4

8:50 am-2:55 pm

1 stop5h 05m

Hartford Bradley Intl

Sun 12/7

7:15 pm-8:45 pm

Nonstop2h 30m

$167

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/31

4:30 pm-10:34 pm

1 stop5h 04m

Hartford Bradley Intl

Sun 2/1

5:30 am-8:54 am

1 stop4h 24m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 12/4

8:50 am-2:55 pm

1 stop5h 05m

Hartford Bradley Intl

Sun 12/7

2:00 pm-8:30 pm

2 stops7h 30m

$182

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 12/5

3:52 pm-2:49 pm

1 stop21h 57m

Hartford Bradley Intl

Mon 12/8

2:07 pm-8:46 am

2 stops19h 39m

$192

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 12/5

3:52 pm-2:49 pm

1 stop21h 57m

Hartford Bradley Intl

Sun 12/7

12:48 pm-6:12 pm

1 stop6h 24m

$195

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 12/12

3:52 pm-2:49 pm

1 stop21h 57m

Hartford Bradley Intl

Sun 12/14

12:48 pm-6:12 pm

1 stop6h 24m

$212

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 11/20

6:20 am-7:32 pm

2 stops12h 12m

Hartford Bradley Intl

Fri 12/5

11:59 am-7:42 pm

1 stop8h 43m

$219

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 12/11

8:50 am-2:55 pm

1 stop5h 05m

Hartford Bradley Intl

Sun 12/14

12:20 pm-7:05 pm

2 stops7h 45m

$227

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 12/6

2:59 pm-11:30 am

2 stops19h 31m

Hartford Bradley Intl

Mon 12/8

2:07 pm-9:58 pm

1 stop8h 51m

$244

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Mon 11/24

5:47 pm-7:32 pm

1 stop24h 45m

Hartford Bradley Intl

Sun 11/30

8:27 pm-5:15 pm

2 stops21h 48m

$306

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 Vermont from

How to get the cheapest flight ticket from Chicago Midway Airport to Vermont

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 Chicago Midway to Vermont?

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

Cheap Chicago Midway Airport to Vermont flight deals and tips

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

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Vermont

2 airports
The fastest flight from Chicago Midway Airport to Vermont takes 1h 50m
Direct flights go from Chicago Midway Airport to Vermont every day.
There are 2 airports near Vermont: Albany Intl (ALB), Hartford Bradley Intl (BDL)
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  • When did momondo last update prices for flights from Chicago Midway Airport to Vermont?

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

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

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

    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 Chicago Midway Airport to Vermont.

  • What documentation or ID do you need to fly to Vermont?

    The travel and health documents required for your trip to Vermont can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Vermont. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Vermont?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Vermont. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Vermont with flexible booking policies on momondo?

momondo does allow users to show only those flights to Vermont from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Vermont?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Vermont from Chicago.

I’m not ready to book a flight from Chicago to Vermont right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Vermont now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Vermont and let you know when they change.

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