$68 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 2/25. 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
$166
Overall average: $359
Frontier
Thu 2/5Mon 2/9
BDL - ORD • 1 stop
Cheapest non-stop
$209
Typical prices: $378-$481
American Airlines
Wed 4/8Sat 4/11
BTV - ORD • Non-stop
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Flight Deals
Useful Info
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

Thu, Feb 5 - Mon, Feb 9
Frontier Logo
8:31 pm - 10:35 am
BDL
-
ORD
15h 04m1 stop
Frontier Logo
11:51 am - 11:24 am
ORD
-
BDL
22h 33m1 stop
$166Frontier
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
10:52 am - 8:27 pm
BDL
-
MDW
10h 35m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$170Frontier
Mon, Mar 9 - Thu, Mar 12
Multiple Airlines Logo
6:00 am - 11:49 am
BDL
-
ORD
6h 49m1 stop
Multiple Airlines Logo
5:01 am - 12:12 pm
ORD
-
BDL
6h 11m1 stop
$182Multiple Airlines
Tue, Feb 10 - Tue, Feb 17
Southwest Logo
5:30 am - 6:55 am
ALB
-
MDW
2h 25mnonstop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$197Southwest
Tue, Feb 10 - Tue, Feb 17
Southwest Logo
1:00 pm - 7:00 pm
ALB
-
MDW
7h 00m1 stop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$207Southwest
Wed, Apr 8 - Sat, Apr 11
American Airlines Logo
6:10 pm - 8:00 pm
BTV
-
ORD
2h 50mnonstop
American Airlines Logo
2:04 pm - 5:25 pm
ORD
-
BTV
2h 21mnonstop
$209American Airlines
Mon, Feb 2 - Wed, Feb 4
Multiple Airlines Logo
10:00 am - 9:12 am
ALB
-
ORD
24h 12m2 stops
Multiple Airlines Logo
12:44 pm - 8:46 am
ORD
-
ALB
19h 02m1 stop
$210Multiple Airlines
Tue, Feb 17 - Tue, Feb 17
Delta Logo
5:30 am - 8:54 am
ALB
-
MDW
4h 24m1 stop
Delta Logo
6:20 pm - 11:24 pm
MDW
-
ALB
4h 04m1 stop
$217Delta
Fri, Apr 3 - Sun, Apr 5
Delta Logo
7:10 am - 12:29 pm
BTV
-
MDW
6h 19m1 stop
Delta Logo
9:35 am - 3:52 pm
MDW
-
BTV
5h 17m1 stop
$229Delta
Fri, May 15 - Mon, May 18
American Airlines Logo
6:10 pm - 8:00 pm
BTV
-
ORD
2h 50mnonstop
American Airlines Logo
6:43 pm - 10:07 pm
ORD
-
BTV
2h 24mnonstop
$247American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$68
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 Hartford 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 $1,262
Business Class flights to Chicagofrom $479
Prem Econ Class flights to Chicagofrom $839
Economy Class flights to Chicagofrom $264