Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Vermont to Chicago from $149

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 8/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Vermont to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:25 pm - 7:35 pm
ALB
-
MDW
2h 10mnonstop
Southwest Logo
6:50 pm - 9:45 pm
MDW
-
ALB
1h 55mnonstop
$268Southwest
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
7:25 am - 8:35 am
ALB
-
MDW
2h 10mnonstop
Southwest Logo
8:05 am - 11:10 am
MDW
-
ALB
2h 05mnonstop
$268Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
3:55 pm - 5:00 pm
ALB
-
MDW
2h 05mnonstop
Southwest Logo
8:05 am - 11:10 am
MDW
-
ALB
2h 05mnonstop
$268Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
6:00 am - 12:05 pm
ALB
-
MDW
7h 05m
2 stops
Southwest Logo
7:45 am - 10:45 am
MDW
-
ALB
2h 00mnonstop
$272Southwest
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
6:35 am - 5:20 pm
ALB
-
MDW
11h 45m
2 stops
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$272Southwest
Tue, Nov 10 - Mon, Nov 16
Southwest Logo
5:20 am - 12:30 pm
ALB
-
MDW
8h 10m
2 stops
Southwest Logo
7:45 am - 10:45 am
MDW
-
ALB
2h 00mnonstop
$272Southwest
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
12:15 pm - 7:25 pm
ALB
-
MDW
8h 10m
2 stops
Southwest Logo
7:45 am - 10:45 am
MDW
-
ALB
2h 00mnonstop
$272Southwest
Wed, Sep 9 - Sat, Sep 12
Southwest Logo
1:20 pm - 8:10 pm
ALB
-
MDW
7h 50m
2 stops
Southwest Logo
6:55 pm - 9:50 pm
MDW
-
ALB
1h 55mnonstop
$272Southwest
Thu, Nov 5 - Mon, Nov 9
Delta Logo
6:00 am - 9:17 am
ALB
-
MDW
4h 17m
1 stop
Delta Logo
6:05 am - 1:26 pm
MDW
-
ALB
6h 21m
1 stop
$277Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
6:00 am - 9:07 am
ALB
-
MDW
4h 07m
1 stop
Delta Logo
4:30 pm - 11:57 pm
MDW
-
ALB
6h 27m
1 stop
$277Delta
Thu, Sep 24 - Sat, Sep 26

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Vermont to Chicago Midway Airport

Our best Southwest deals on Vermont to Chicago Midway Airport flight tickets
Southwest
Sep 5
ALB7:25 amAlbany Intl
2h 10m
MDW8:35 amChicago Midway
Sep 7
MDW8:05 amChicago Midway
2h 05m
ALB11:10 amAlbany Intl
$268
Southwest
Aug 29
ALB5:20 amAlbany Intl
8h 10m
2 stops
MDW12:30 pmChicago Midway
Sep 5
MDW7:45 amChicago Midway
2h 00m
ALB10:45 amAlbany Intl
$272
Southwest
Sep 5
BDL7:55 amHartford Bradley Intl
2h 20m
MDW9:15 amChicago Midway
Sep 6
MDW8:45 amChicago Midway
2h 15m
BDL12:00 pmHartford Bradley Intl
$277

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
Sep 5
ALB6:00 amAlbany Intl
4h 17m
1 stop
MDW9:17 amChicago Midway
Sep 6
MDW6:05 amChicago Midway
6h 21m
1 stop
ALB1:26 pmAlbany Intl
$277
Delta
Aug 20
BDL7:00 amHartford Bradley Intl
5h 51m
1 stop
MDW11:51 amChicago Midway
Aug 24
MDW6:42 pmChicago Midway
4h 09m
1 stop
BDL11:51 pmHartford Bradley Intl
$297
Delta
Oct 1
ALB6:00 amAlbany Intl
4h 07m
1 stop
MDW9:07 amChicago Midway
Oct 3
MDW4:30 pmChicago Midway
6h 27m
1 stop
ALB11:57 pmAlbany Intl
$299

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 August 3, 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
Quickest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 10/27

6:25 pm-7:35 pm

Nonstop2h 10m

Chicago Midway

Fri 10/30

6:50 pm-9:45 pm

Nonstop1h 55m

$268

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 9/5

7:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Mon 9/7

8:05 am-11:10 am

Nonstop2h 05m

$268

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 9/5

3:55 pm-5:00 pm

Nonstop2h 05m

Chicago Midway

Mon 9/7

8:05 am-11:10 am

Nonstop2h 05m

$268

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 9/2

6:00 am-12:05 pm

2 stops7h 05m

Chicago Midway

Sat 9/5

7:45 am-10:45 am

Nonstop2h 00m

$272

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 11/10

6:35 am-5:20 pm

2 stops11h 45m

Chicago Midway

Mon 11/16

1:25 pm-4:15 pm

Nonstop1h 50m

$272

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 8/29

5:20 am-12:30 pm

2 stops8h 10m

Chicago Midway

Sat 9/5

7:45 am-10:45 am

Nonstop2h 00m

$272

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Wed 9/9

12:15 pm-7:25 pm

2 stops8h 10m

Chicago Midway

Sat 9/12

7:45 am-10:45 am

Nonstop2h 00m

$272

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 11/5

1:20 pm-8:10 pm

2 stops7h 50m

Chicago Midway

Mon 11/9

6:55 pm-9:50 pm

Nonstop1h 55m

$272

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 9/5

6:00 am-9:17 am

1 stop4h 17m

Chicago Midway

Sun 9/6

6:05 am-1:26 pm

1 stop6h 21m

$277

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 9/24

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Sat 9/26

4:30 pm-11:57 pm

1 stop6h 27m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 76% 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.
Search flight deals

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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 9/2
Wed 9/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago