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>

$79 CHEAP FLIGHTS from Vermont to Chicago

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

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Flights 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

Thu, Aug 7 - Sun, Aug 10

5:25 pm - 6:45 pmBDL-MDW

2h 20mnonstop

10:00 am - 1:10 pmMDW-BDL

2h 10mnonstop

$157Southwest

Find Deal

Mon, Aug 25 - Wed, Aug 27

6:10 am - 7:53 amBDL-ORD

2h 43mnonstop

11:06 am - 2:24 pmORD-BDL

2h 18mnonstop

$157United Airlines

Find Deal

Fri, Aug 22 - Mon, Aug 25

9:44 am - 7:19 pmBDL-ORD

10h 35m1 stop

8:14 pm - 8:49 amORD-BDL

11h 35m1 stop

$193Spirit Airlines

Find Deal

Wed, Aug 6 - Sat, Aug 9

11:54 am - 1:38 pmBDL-ORD

2h 44mnonstop

8:30 pm - 11:59 pmORD-BDL

2h 29mnonstop

$194American Airlines

Find Deal

Wed, Jul 2 - Mon, Jul 7

6:27 am - 8:07 amBTV-ORD

2h 40mnonstop

2:03 pm - 5:21 pmORD-BTV

2h 18mnonstop

$194American Airlines

Find Deal

Fri, Aug 15 - Mon, Aug 18

11:25 am - 4:48 pmBDL-ORD

6h 23m1 stop

8:14 pm - 8:49 amORD-BDL

11h 35m1 stop

$195Spirit Airlines

Find Deal

Mon, Aug 11 - Tue, Aug 19

7:04 pm - 11:56 pmBDL-ORD

5h 52m1 stop

7:15 am - 12:03 pmORD-BDL

3h 48m1 stop

$197Delta

Find Deal

Fri, Jul 4 - Sat, Jul 19

7:20 am - 12:29 pmBTV-MDW

6h 09m1 stop

5:53 pm - 10:59 pmMDW-BTV

4h 06m1 stop

$214Delta

Find Deal

Mon, Jul 7 - Thu, Jul 10

10:58 am - 5:21 pmBDL-ORD

7h 23m1 stop

11:11 am - 9:20 amORD-BDL

21h 09m1 stop

$239

Find Deal

Fri, Sep 12 - Sun, Sep 14

11:00 am - 4:18 pmALB-ORD

6h 18m1 stop

4:12 pm - 5:16 pmORD-ALB

24h 04m1 stop

$258

Find Deal

Useful Info

Low season	January
High season	August
Cheapest flight	$79

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 10% lower on average.

Flight from Hartford to Chicago Midway 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.

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 $687

Business Class flights to Chicagofrom $446

Prem Econ Class flights to Chicagofrom $541

Economy Class flights to Chicagofrom $262

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$79 Find Cheap Flights from Vermont to Chicago

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

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.

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