How does KAYAK find such low prices on flights from Vermont to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Vermont to Chicago. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Vermont to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Vermont is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Vermont to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Vermont with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Vermont to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Vermont up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

$69 CHEAP FLIGHTS from Vermont to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$225

Overall average: $377

Southwest

Sun 2/22Sat 2/28

BDL - MDW • Non-stop

Cheapest one-way

$69

Typical prices: $147-$309

Frontier

Sat 11/22

BTV - ORD • 1 stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

Flight Deals

Cheap Flights from Vermont to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Vermont to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Vermont to Chicago

Sun, Feb 22 - Sat, Feb 28

5:10 am - 6:45 amBDL-MDW

2h 35mnonstop

6:05 pm - 9:05 pmMDW-BDL

2h 00mnonstop

$225Southwest

Find Deal

Fri, Dec 12 - Mon, Dec 15

11:59 am - 10:24 pmBDL-ORD

11h 25m1 stop

6:11 am - 5:26 pmORD-BDL

10h 15m2 stops

$225Multiple Airlines

Find Deal

Thu, Dec 11 - Tue, Dec 16

7:25 am - 1:00 pmBDL-MDW

6h 35m2 stops

12:55 pm - 8:05 pmMDW-BDL

6h 10m1 stop

$227Southwest

Find Deal

Thu, Dec 18 - Mon, Dec 22

12:05 pm - 5:38 pmBDL-MDW

6h 33m1 stop

6:15 am - 3:29 pmMDW-BDL

8h 14m1 stop

$228Frontier

Find Deal

Thu, Dec 11 - Sun, Dec 14

5:52 am - 7:55 amBDL-ORD

3h 03mnonstop

8:35 pm - 11:56 pmORD-BDL

2h 21mnonstop

$231American Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 7

5:52 am - 7:55 amBDL-ORD

3h 03mnonstop

8:35 pm - 11:56 pmORD-BDL

2h 21mnonstop

$233American Airlines

Find Deal

Tue, Dec 2 - Tue, Dec 9

7:05 am - 4:45 pmBTV-ORD

10h 40m2 stops

6:00 am - 4:15 pmORD-BTV

9h 15m2 stops

$239Delta

Find Deal

Tue, Mar 3 - Wed, Mar 4

5:30 am - 8:54 amBDL-MDW

4h 24m1 stop

9:34 am - 4:22 pmMDW-BDL

5h 48m1 stop

$245Delta

Find Deal

Sun, Jan 18 - Fri, May 8

6:12 am - 8:05 amBTV-ORD

2h 53mnonstop

10:42 am - 1:57 pmORD-BTV

2h 15mnonstop

$248United Airlines

Find Deal

Tue, Dec 16 - Wed, Dec 24

4:17 pm - 6:05 pmALB-ORD

2h 48mnonstop

6:00 pm - 9:05 pmORD-ALB

2h 05mnonstop

$250United Airlines

Find Deal

Useful Info

Low season	January
High season	July
Cheapest flight	$69

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 2% increase in price.

Flight from Burlington to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Vermont to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Vermont to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Vermont to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Vermont is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Vermont to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Vermont with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Vermont to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Vermont up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Vermont

First Class flights to Chicagofrom $698

Business Class flights to Chicagofrom $1,173

Prem Econ Class flights to Chicagofrom $1,615

Economy Class flights to Chicagofrom $261

$95 Find Cheap Flights from Vermont to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

Cheap Flights from Vermont to Chicago

Recent round-trip flight deals from Vermont to Chicago

Recent one-way flight deals from Vermont to Chicago

Recent last minute flight deals from Vermont to Chicago

Recent direct flight deals from Vermont to Chicago

Good to know

FAQs for booking flights from Vermont to Chicago

How does KAYAK find such low prices on flights from Vermont to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Vermont to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Vermont to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Vermont is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Vermont to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Vermont with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Vermont to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Vermont up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Vermont

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight