Latest deals
Insights
FAQs
Price Alerts

Cheap flights from Vermont to Chicago from $117

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 4/23. 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
0 bags

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

Find the cheapest flights from Vermont to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:40 am - 10:14 am
BTV
-
MDW
5h 34m
1 stop
Delta Logo
5:10 pm - 11:44 pm
MDW
-
BTV
5h 34m
1 stop
$289Delta
Sat, May 2 - Sat, May 9
Delta Logo
5:40 am - 10:14 am
BTV
-
MDW
5h 34m
1 stop
Delta Logo
6:38 pm - 11:17 pm
MDW
-
BTV
3h 39m
1 stop
$291Delta
Sat, May 2 - Sat, May 2
Delta Logo
10:50 am - 5:58 pm
BTV
-
MDW
8h 08m
2 stops
Delta Logo
5:10 pm - 11:44 pm
MDW
-
BTV
5h 34m
1 stop
$294Delta
Sat, May 2 - Sat, May 9
Southwest Logo
6:40 pm - 7:50 pm
ALB
-
MDW
2h 10mnonstop
Southwest Logo
5:00 pm - 10:05 pm
MDW
-
ALB
4h 05m
1 stop
$295Southwest
Tue, May 26 - Wed, Jun 3
Southwest Logo
9:30 am - 1:10 pm
ALB
-
MDW
4h 40m
1 stop
Southwest Logo
12:45 pm - 3:40 pm
MDW
-
ALB
1h 55mnonstop
$297Southwest
Sat, May 16 - Tue, May 19
Multiple Airlines Logo
6:41 pm - 5:54 pm
ALB
-
MDW
24h 13m
1 stop
Multiple Airlines Logo
2:15 pm - 11:21 am
MDW
-
ALB
20h 06m
2 stops
$298Multiple Airlines
Thu, Apr 23 - Wed, Apr 29
Southwest Logo
7:50 am - 9:05 am
ALB
-
MDW
2h 15mnonstop
Southwest Logo
9:10 am - 2:30 pm
MDW
-
ALB
4h 20m
1 stop
$299Southwest
Sat, May 2 - Sat, May 9
Frontier Logo
8:42 pm - 7:59 am
BDL
-
MDW
12h 17m
1 stop
Frontier Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$332Frontier
Sat, Apr 18 - Fri, Apr 24
Frontier Logo
3:50 pm - 10:19 pm
BDL
-
MDW
7h 29m
1 stop
Frontier Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$337Frontier
Sun, Apr 19 - Thu, Apr 23
Multiple Airlines Logo
9:10 am - 7:31 pm
BDL
-
MDW
11h 21m
2 stops
Multiple Airlines Logo
2:15 pm - 2:49 pm
MDW
-
BDL
23h 34m
1 stop
$340Multiple Airlines
Tue, Apr 21 - Wed, Apr 22

Delta flights from Vermont to Chicago Midway Airport

Our best Delta deals on Vermont to Chicago Midway Airport flight tickets
Delta
May 2
BTV5:40 amBurlington
5h 34m
1 stop
MDW10:14 amChicago Midway
May 9
MDW5:10 pmChicago Midway
5h 34m
1 stop
BTV11:44 pmBurlington
$289
Delta
May 2
BTV5:40 amBurlington
5h 34m
1 stop
MDW10:14 amChicago Midway
May 2
MDW6:38 pmChicago Midway
3h 39m
1 stop
BTV11:17 pmBurlington
$291
Delta
May 2
BTV10:50 amBurlington
8h 08m
2 stops
MDW5:58 pmChicago Midway
May 9
MDW5:10 pmChicago Midway
5h 34m
1 stop
BTV11:44 pmBurlington
$294

Frontier flights from Vermont to Chicago Midway Airport

Our best Frontier deals on Vermont to Chicago Midway Airport flight tickets
Frontier
Apr 18
BDL8:42 pmHartford Bradley Intl
12h 17m
1 stop
MDW7:59 amChicago Midway
Apr 24
MDW6:00 amChicago Midway
7h 49m
1 stop
BDL2:49 pmHartford Bradley Intl
$332
Frontier
Apr 19
BDL3:50 pmHartford Bradley Intl
7h 29m
1 stop
MDW10:19 pmChicago Midway
Apr 23
MDW6:00 amChicago Midway
7h 49m
1 stop
BDL2:49 pmHartford Bradley Intl
$337
Frontier
Apr 23
BDL3:50 pmHartford Bradley Intl
7h 29m
1 stop
MDW10:19 pmChicago Midway
Apr 25
MDW7:34 pmChicago Midway
18h 15m
1 stop
BDL2:49 pmHartford Bradley Intl
$347

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 April 7, 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

Sat 5/2

5:40 am-10:14 am

1 stop5h 34m

Chicago Midway

Sat 5/9

5:10 pm-11:44 pm

1 stop5h 34m

$289

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 5/2

5:40 am-10:14 am

1 stop5h 34m

Chicago Midway

Sat 5/2

6:38 pm-11:17 pm

1 stop3h 39m

$291

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 5/2

10:50 am-5:58 pm

2 stops8h 08m

Chicago Midway

Sat 5/9

5:10 pm-11:44 pm

1 stop5h 34m

$294
Quickest round-trip

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Tue 5/26

6:40 pm-7:50 pm

Nonstop2h 10m

Chicago Midway

Wed 6/3

5:00 pm-10:05 pm

1 stop4h 05m

$295

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 5/16

9:30 am-1:10 pm

1 stop4h 40m

Chicago Midway

Tue 5/19

12:45 pm-3:40 pm

Nonstop1h 55m

$297

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Thu 4/23

6:41 pm-5:54 pm

1 stop24h 13m

Chicago Midway

Wed 4/29

2:15 pm-11:21 am

2 stops20h 06m

$298

AlbanyChicago

ALB - MDW

ALBMDW

Albany Intl

Sat 5/2

7:50 am-9:05 am

Nonstop2h 15m

Chicago Midway

Sat 5/9

9:10 am-2:30 pm

1 stop4h 20m

$299

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 4/18

8:42 pm-7:59 am

1 stop12h 17m

Chicago Midway

Fri 4/24

6:00 am-2:49 pm

1 stop7h 49m

$332

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 4/19

3:50 pm-10:19 pm

1 stop7h 29m

Chicago Midway

Thu 4/23

6:00 am-2:49 pm

1 stop7h 49m

$337

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 4/21

9:10 am-7:31 pm

2 stops11h 21m

Chicago Midway

Wed 4/22

2:15 pm-2:49 pm

1 stop23h 34m

$340

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

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
Thu 5/7
Thu 5/14
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago