$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 1/12. 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
$170
Overall average: $323
Multiple Airlines
Mon 1/12Thu 1/15
BDL - ORD • 1 stop
Cheapest non-stop
$225
Typical prices: $327-$468
American Airlines
Wed 2/11Sat 2/14
BDL - ORD • Non-stop
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We hope you love your trip to Chicago!
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

Mon, Jan 12 - Thu, Jan 15
Multiple Airlines Logo
8:19 pm - 5:52 pm
BDL
-
ORD
22h 33m1 stop
Multiple Airlines Logo
7:45 am - 4:03 pm
ORD
-
BDL
7h 18m1 stop
$170Multiple Airlines
Mon, Jan 12 - Thu, Jan 15
Multiple Airlines Logo
8:19 pm - 1:13 pm
BDL
-
ORD
17h 54m1 stop
Multiple Airlines Logo
8:08 pm - 10:53 pm
ORD
-
BDL
25h 45m2 stops
$174Multiple Airlines
Sat, Jan 17 - Sun, Jan 18
Delta Logo
11:22 am - 4:29 pm
BDL
-
MDW
6h 07m1 stop
Delta Logo
6:14 pm - 11:40 pm
MDW
-
BDL
4h 26m1 stop
$177Delta
Mon, Jan 12 - Wed, Jan 14
Frontier Logo
8:19 pm - 12:08 pm
BDL
-
ORD
16h 49m2 stops
Frontier Logo
5:57 pm - 10:51 am
ORD
-
BDL
15h 54m1 stop
$180Frontier
Mon, Jan 12 - Wed, Jan 14
Frontier Logo
8:19 pm - 12:08 pm
BDL
-
ORD
16h 49m2 stops
Frontier Logo
5:57 pm - 10:51 am
ORD
-
BDL
15h 54m1 stop
$190Frontier
Wed, Jan 14 - Sat, Jan 17
Delta Logo
5:40 am - 8:52 am
BDL
-
MDW
4h 12m1 stop
Delta Logo
6:45 am - 1:33 pm
MDW
-
BDL
5h 48m1 stop
$245Delta
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
3:35 pm - 7:00 pm
ALB
-
MDW
4h 25m1 stop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$256Southwest
Tue, Jan 20 - Tue, Jan 20
Southwest Logo
5:30 am - 6:55 am
ALB
-
MDW
2h 25mnonstop
Southwest Logo
1:25 pm - 4:15 pm
MDW
-
ALB
1h 50mnonstop
$258Southwest
Sat, Jan 17 - Mon, Jan 19
American Airlines Logo
9:00 am - 10:53 am
ALB
-
ORD
2h 53mnonstop
American Airlines Logo
1:25 pm - 4:31 pm
ORD
-
ALB
2h 06mnonstop
$258American Airlines
Sat, Jan 17 - Sun, Jan 18
American Airlines Logo
9:00 am - 10:53 am
ALB
-
ORD
2h 53mnonstop
American Airlines Logo
6:00 am - 11:37 am
ORD
-
ALB
4h 37m1 stop
$268American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Hartford 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
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 $479
Business Class flights to Chicagofrom $1,663
Prem Econ Class flights to Chicagofrom $1,202
Economy Class flights to Chicagofrom $275