$71 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 12/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$201
Overall average: $379
Frontier
Sat 11/15Sun 11/16
BDL - MDW • 1 stop
Cheapest non-stop
$206
Typical prices: $333-$464
American Airlines
Fri 12/12Tue 12/16
BDL - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Sat, Nov 15 - Sun, Nov 16
Frontier Logo
11:13 am - 6:39 pmBDL-MDW
8h 26m1 stop
Frontier Logo
10:12 am - 2:12 pmMDW-BDL
27h 00m1 stop
$201Frontier
Find Deal
Wed, Dec 3 - Wed, Dec 3
United Airlines Logo
6:00 am - 9:36 amBDL-ORD
4h 36m1 stop
United Airlines Logo
6:15 pm - 11:59 pmORD-BDL
4h 44m1 stop
$201United Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Multiple Airlines Logo
1:36 pm - 10:10 pmBDL-MDW
9h 34m1 stop
Multiple Airlines Logo
6:06 pm - 12:13 pmMDW-BDL
17h 07m2 stops
$202Multiple Airlines
Find Deal
Sun, Nov 23 - Wed, Nov 26
Multiple Airlines Logo
8:27 pm - 11:06 pmBDL-ORD
27h 39m1 stop
Multiple Airlines Logo
6:15 pm - 7:32 pmORD-BDL
24h 17m1 stop
$202Multiple Airlines
Find Deal
Sat, Nov 8 - Mon, Nov 10
JetBlue Logo
7:10 am - 8:52 pmBDL-ORD
14h 42m1 stop
JetBlue Logo
6:45 am - 11:59 pmORD-BDL
16h 14m1 stop
$203JetBlue
Find Deal
Wed, Dec 10 - Sun, Dec 14
American Airlines Logo
12:07 pm - 4:51 pmBDL-ORD
5h 44m1 stop
American Airlines Logo
8:35 pm - 11:56 pmORD-BDL
2h 21mnonstop
$204American Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
American Airlines Logo
6:08 am - 11:03 amBDL-ORD
5h 55m1 stop
American Airlines Logo
8:35 pm - 11:56 pmORD-BDL
2h 21mnonstop
$206American Airlines
Find Deal
Mon, Dec 15 - Wed, Dec 17
Southwest Logo
5:15 am - 6:45 amBDL-MDW
2h 30mnonstop
Southwest Logo
8:50 am - 2:55 pmMDW-BDL
5h 05m1 stop
$207Southwest
Find Deal
Wed, Nov 5 - Thu, Nov 6
JetBlue Logo
7:00 am - 8:52 pmBDL-ORD
14h 52m1 stop
JetBlue Logo
7:45 am - 11:59 pmORD-BDL
15h 14m1 stop
$223JetBlue
Find Deal
Wed, Nov 12 - Thu, Nov 13
Southwest Logo
5:15 am - 6:45 amBDL-MDW
2h 30mnonstop
Southwest Logo
11:55 am - 2:55 pmMDW-BDL
2h 00mnonstop
$225Southwest
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$71
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 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
Munster
Schererville
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 $489
Prem Econ Class flights to Chicagofrom $1,694
Economy Class flights to Chicagofrom $250

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.