$103 Find Cheap Flights from Vermont to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$225
Overall average: $399
Multiple Airlines
Fri 12/12Mon 12/15
BDL - ORD • 1 stop
Cheapest non-stop
$225
Typical prices: $333-$466
American Airlines
Wed 12/3Tue 12/9
BDL - ORD • Non-stop
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Flight Deals
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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.

Recent round-trip flight deals from Vermont to Chicago

Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
11:59 am - 10:24 pmBDL-ORD
11h 25m1 stop
Multiple Airlines Logo
6:11 am - 5:26 pmORD-BDL
10h 15m2 stops
$225Multiple Airlines
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Thu, Dec 4 - Fri, Dec 5
Southwest Logo
7:25 am - 1:45 pmBDL-MDW
7h 20m1 stop
Southwest Logo
1:45 pm - 4:45 pmMDW-BDL
2h 00mnonstop
$226Southwest
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Sat, Dec 6 - Tue, Dec 9
United Airlines Logo
6:00 am - 9:36 amBDL-ORD
4h 36m1 stop
United Airlines Logo
11:06 am - 2:16 pmORD-BDL
2h 10mnonstop
$226United Airlines
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Thu, Dec 11 - Sun, Dec 14
United Airlines Logo
6:10 am - 8:01 amBDL-ORD
2h 51mnonstop
United Airlines Logo
11:06 am - 2:16 pmORD-BDL
2h 10mnonstop
$227United Airlines
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Fri, Dec 12 - Sun, Dec 14
Frontier Logo
11:59 am - 7:42 pmBDL-MDW
8h 43m1 stop
Frontier Logo
6:37 pm - 1:12 pmMDW-BDL
17h 35m1 stop
$227Frontier
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Tue, Nov 18 - Mon, Nov 24
Delta Logo
9:43 am - 12:34 pmBDL-MDW
3h 51m1 stop
Delta Logo
6:48 pm - 11:22 pmMDW-BDL
3h 34m1 stop
$232Delta
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Thu, Dec 11 - Mon, Dec 15
Delta Logo
5:23 am - 8:54 amBDL-MDW
4h 31m1 stop
Delta Logo
6:40 pm - 11:38 pmMDW-BDL
3h 58m1 stop
$236Delta
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Wed, Dec 3 - Wed, Dec 10
JetBlue Logo
7:02 am - 9:52 pmBDL-ORD
15h 50m1 stop
JetBlue Logo
7:00 am - 10:42 pmORD-BDL
14h 42m1 stop
$243JetBlue
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Fri, Dec 5 - Mon, Dec 8
JetBlue Logo
7:02 am - 9:52 pmBDL-ORD
15h 50m1 stop
JetBlue Logo
7:00 am - 10:42 pmORD-BDL
14h 42m1 stop
$249JetBlue
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Thu, Nov 20 - Tue, Nov 25
Frontier Logo
10:54 am - 2:40 pmBDL-MDW
28h 46m1 stop
Frontier Logo
4:00 pm - 9:52 amMDW-BDL
40h 52m2 stops
$253Frontier
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$103
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 Albany to Chicago Midway Airport

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?

Book flights to Chicago if you plan to visit one of these locations
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 types available on flights to Vermont

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
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