$106 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 8/25. 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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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

Tue, Jul 28 - Sat, Aug 1
Delta Logo
1:20 pm - 6:29 pm
BTV
-
ORD
6h 09m
1 stop
Delta Logo
5:18 pm - 11:11 pm
ORD
-
BTV
4h 53m
1 stop
$260Delta
Thu, Jul 23 - Mon, Jul 27
United Airlines Logo
4:57 pm - 6:40 pm
BTV
-
ORD
2h 43mnonstop
United Airlines Logo
6:15 pm - 9:34 pm
ORD
-
BTV
2h 19mnonstop
$269United Airlines
Fri, Jun 26 - Mon, Jul 6
American Airlines Logo
7:47 pm - 9:40 pm
BTV
-
ORD
2h 53mnonstop
American Airlines Logo
8:47 pm - 12:09 am
ORD
-
BTV
2h 22mnonstop
$270American Airlines
Thu, Jun 25 - Sun, Jun 28
American Airlines Logo
6:33 am - 8:26 am
BTV
-
ORD
2h 53mnonstop
American Airlines Logo
8:35 pm - 11:58 pm
ORD
-
BTV
2h 23mnonstop
$271American Airlines
Thu, Jul 23 - Tue, Jul 28
United Airlines Logo
4:57 pm - 6:40 pm
BTV
-
ORD
2h 43mnonstop
United Airlines Logo
7:10 am - 3:10 pm
ORD
-
BTV
7h 00m
1 stop
$279United Airlines
Sat, Jun 20 - Sun, Jun 21
Southwest Logo
6:10 pm - 7:30 pm
ALB
-
MDW
2h 20mnonstop
Southwest Logo
7:40 pm - 10:35 pm
MDW
-
ALB
1h 55mnonstop
$335Southwest
Sun, Aug 23 - Thu, Aug 27
Multiple Airlines Logo
1:15 pm - 12:25 pm
ALB
-
ORD
24h 10m
1 stop
Multiple Airlines Logo
12:30 pm - 11:09 am
ORD
-
ALB
21h 39m
2 stops
$335Multiple Airlines
Fri, Jun 26 - Mon, Jun 29
Multiple Airlines Logo
7:53 pm - 12:24 pm
ALB
-
ORD
17h 31m
1 stop
Multiple Airlines Logo
7:52 am - 7:03 pm
ORD
-
ALB
10h 11m
1 stop
$336Multiple Airlines
Wed, Jul 1 - Tue, Jul 21
Southwest Logo
6:55 pm - 8:15 pm
ALB
-
MDW
2h 20mnonstop
Southwest Logo
7:45 am - 10:45 am
MDW
-
ALB
2h 00mnonstop
$338Southwest
Fri, Jul 10 - Sun, Jul 12
Sun Country Air Logo
7:18 pm - 5:19 pm
BDL
-
ORD
23h 01m
1 stop
Sun Country Air Logo
6:31 pm - 10:04 am
ORD
-
BDL
14h 33m
1 stop
$355Sun Country Air
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$105
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly with an average 8% 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
Schererville
Chesterton
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 $1,743
Business Class flights to Chicagofrom $497
Premium Economy Class flights to Chicagofrom $1,872
Economy Class flights to Chicagofrom $307