$97 Find Cheap Flights from Vermont to Chicago - Compare and Save

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 10/27. 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

Sat, Sep 5 - Mon, Sep 7
American Airlines Logo
8:13 pm - 10:00 pm
ALB
-
ORD
2h 47mnonstop
American Airlines Logo
4:24 pm - 7:41 pm
ORD
-
ALB
2h 17mnonstop
$268American Airlines
Tue, Oct 27 - Fri, Oct 30
American Airlines Logo
12:07 pm - 1:50 pm
ALB
-
ORD
2h 43mnonstop
American Airlines Logo
8:18 am - 11:36 am
ORD
-
ALB
2h 18mnonstop
$268American Airlines
Mon, Sep 7 - Fri, Sep 11
United Airlines Logo
8:10 am - 9:45 am
ALB
-
ORD
2h 35mnonstop
United Airlines Logo
11:59 am - 3:04 pm
ORD
-
ALB
2h 05mnonstop
$268United Airlines
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
6:25 pm - 7:35 pm
ALB
-
MDW
2h 10mnonstop
Southwest Logo
6:50 pm - 9:45 pm
MDW
-
ALB
1h 55mnonstop
$268Southwest
Sat, Sep 5 - Mon, Sep 7
Southwest Logo
7:25 am - 8:35 am
ALB
-
MDW
2h 10mnonstop
Southwest Logo
8:05 am - 11:10 am
MDW
-
ALB
2h 05mnonstop
$268Southwest
Sun, Sep 27 - Sat, Oct 3
Multiple Airlines Logo
11:15 am - 9:20 am
ALB
-
ORD
23h 05m
2 stops
Multiple Airlines Logo
7:11 am - 12:15 pm
ORD
-
ALB
28h 04m
1 stop
$273Multiple Airlines
Sat, Oct 3 - Tue, Oct 6
United Airlines Logo
12:38 pm - 2:23 pm
BDL
-
ORD
2h 45mnonstop
United Airlines Logo
7:30 am - 10:49 am
ORD
-
BDL
2h 19mnonstop
$277United Airlines
Sat, Sep 5 - Sun, Sep 6
Delta Logo
2:32 pm - 8:55 pm
ALB
-
ORD
7h 23m
1 stop
Delta Logo
6:40 am - 1:26 pm
ORD
-
ALB
5h 46m
1 stop
$277Delta
Tue, Sep 8 - Sat, Sep 12
Delta Logo
6:28 pm - 11:59 pm
ALB
-
ORD
6h 31m
1 stop
Delta Logo
11:17 am - 4:18 pm
ORD
-
ALB
4h 01m
1 stop
$277Delta
Tue, Aug 25 - Sun, Aug 30
Frontier Logo
1:42 pm - 11:27 pm
BDL
-
ORD
10h 45m
1 stop
Frontier Logo
12:44 am - 12:47 pm
ORD
-
BDL
11h 03m
1 stop
$279Frontier
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Good to know

Low season

January

Cheapest flight

$97
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Burlington to Chicago O'Hare 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
Munster
Schererville
Chesterton
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 $497
Business Class flights to Chicagofrom $569
Premium Economy Class flights to Chicagofrom $2,015
Economy Class flights to Chicagofrom $279