$75 Find Cheap Flights from Virginia 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 9/15. 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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Cheap Flights from Virginia to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Virginia 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 Virginia to Chicago

Tue, Sep 8 - Fri, Sep 11
Frontier Logo
6:20 am - 10:55 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
5h 35m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 5:18 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
9h 53m1 stop Atlanta Hartsfield-Jackson
$181Frontier
Fri, Sep 25 - Mon, Sep 28
Frontier Logo
7:50 am - 5:51 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
11h 01m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 5:18 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
9h 53m1 stop Atlanta Hartsfield-Jackson
$182Frontier
Wed, Nov 18 - Thu, Nov 19
Southwest Logo
2:40 pm - 5:45 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
4h 05m1 stop Lambert-St Louis
Southwest Logo
7:25 am - 10:15 amMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$183Southwest
Wed, Nov 11 - Sat, Nov 14
Southwest Logo
2:40 pm - 5:45 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
4h 05m1 stop Lambert-St Louis
Southwest Logo
11:05 am - 1:55 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$183Southwest
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
6:30 am - 7:58 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 28mnonstop
American Airlines Logo
7:47 am - 10:52 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 05mnonstop
$184American Airlines
Wed, Oct 28 - Fri, Oct 30
American Airlines Logo
11:30 am - 12:52 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 22mnonstop
American Airlines Logo
6:55 pm - 10:00 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 05mnonstop
$184American Airlines
Fri, Sep 11 - Mon, Sep 14
United Airlines Logo
6:13 am - 7:27 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mnonstop
United Airlines Logo
8:42 am - 11:49 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 07mnonstop
$184United Airlines
Wed, Oct 28 - Fri, Oct 30
United Airlines Logo
6:11 am - 7:30 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 19mnonstop
United Airlines Logo
6:07 pm - 9:10 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 03mnonstop
$184United Airlines
Tue, Sep 15 - Sat, Sep 26
Multiple Airlines Logo
9:04 pm - 11:51 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
15h 47m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:11 am - 6:33 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
10h 22m2 stops Fort Lauderdale Tampa
$194Multiple Airlines
Sun, Oct 4 - Wed, Oct 7
Multiple Airlines Logo
1:56 pm - 9:20 amRDU  Raleigh-Durham-ORD Chicago O'Hare Intl
20h 24m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
7:11 am - 10:02 amORD  Chicago O'Hare Intl-RDU Raleigh-Durham
25h 51m2 stops Fort Lauderdale Tallahassee
$232Multiple Airlines
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Good to know

Low season

January

Cheapest flight

$75
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Norfolk to Chicago O'Hare Airport

FAQs for booking flights from Virginia to Chicago

  • How does KAYAK find such low prices on flights from Virginia 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 Virginia to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Virginia to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Virginia 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 Virginia 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 Virginia with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Virginia 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 Virginia 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 Virginia

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 $430
Business Class flights to Chicagofrom $534
Premium Economy Class flights to Chicagofrom $499
Economy Class flights to Chicagofrom $233