$89 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 9/14. 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

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
6:55 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 04mnonstop
$185American Airlines
Mon, Aug 31 - Thu, Sep 10
Frontier Logo
6:09 pm - 12:50 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
19h 41m1 stop Fort Lauderdale
Frontier Logo
7:28 pm - 5:18 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
20h 50m1 stop Atlanta Hartsfield-Jackson
$187Frontier
Sun, Sep 6 - Fri, Sep 11
Southwest Logo
9:00 pm - 10:05 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
3:20 pm - 10:30 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
6h 10m1 stop Nashville Intl
$187Southwest
Sun, Sep 6 - Fri, Sep 11
Southwest Logo
6:15 pm - 7:20 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
3:10 pm - 10:45 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
6h 35m1 stop Atlanta Hartsfield-Jackson
$187Southwest
Fri, Sep 11 - Mon, Sep 14
Frontier Logo
10:27 pm - 11:40 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 13mnonstop
Frontier Logo
10:26 am - 5:18 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 52m1 stop Atlanta Hartsfield-Jackson
$188Frontier
Thu, Oct 1 - Mon, Oct 5
American Airlines Logo
8:40 am - 10:10 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 30mnonstop
American Airlines Logo
7:55 am - 10:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 04mnonstop
$191American Airlines
Sat, Sep 5 - Sun, Sep 6
Delta Logo
5:47 pm - 11:57 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
7h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:40 am - 1:43 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
6h 03m1 stop Atlanta Hartsfield-Jackson
$197Delta
Fri, Sep 11 - Fri, Sep 11
Delta Logo
6:10 am - 10:37 amIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 27m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:10 pm - 11:14 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
5h 04m1 stop Detroit Metropolitan Wayne County
$197Delta
Wed, Sep 2 - Sat, Sep 5
United Airlines Logo
10:27 pm - 11:40 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 13mnonstop
United Airlines Logo
2:30 pm - 5:37 pmORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 07mnonstop
$216United Airlines
Fri, Oct 30 - Tue, Nov 3
United Airlines Logo
10:25 pm - 11:39 pmIAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mnonstop
United Airlines Logo
6:04 am - 8:58 amORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
1h 54mnonstop
$216United Airlines
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Good to know

Low season

January

Cheapest flight

$89
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Reagan Washington National Airport 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
Munster
Chesterton
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 $537
Business Class flights to Chicagofrom $592
Premium Economy Class flights to Chicagofrom $499
Economy Class flights to Chicagofrom $233