$99 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 8/1. 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 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, Jul 21 - Fri, Jul 24
Multiple Airlines Logo
1:25 pm - 7:15 pm
DCA
-
ORD
6h 50m
1 stop
Multiple Airlines Logo
9:57 pm - 12:51 pm
ORD
-
DCA
13h 54m
1 stop
$245Multiple Airlines
Tue, Jul 14 - Wed, Jul 22
Frontier Logo
5:40 pm - 12:15 pm
IAD
-
ORD
19h 35m
1 stop
Frontier Logo
7:05 am - 5:14 pm
ORD
-
IAD
9h 09m
1 stop
$245Frontier
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
9:15 pm - 10:10 pm
DCA
-
MDW
1h 55mnonstop
Southwest Logo
9:00 pm - 11:55 pm
MDW
-
DCA
1h 55mnonstop
$245Southwest
Sat, Jul 25 - Mon, Aug 3
Frontier Logo
6:49 am - 11:07 am
IAD
-
MDW
5h 18m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$245Frontier
Thu, Aug 20 - Mon, Aug 24
JetBlue Logo
11:00 am - 7:27 pm
DCA
-
ORD
9h 27m
1 stop
JetBlue Logo
8:20 pm - 7:58 am
ORD
-
DCA
10h 38m
1 stop
$246JetBlue
Wed, Jul 29 - Mon, Aug 3
Southwest Logo
9:30 am - 10:25 am
DCA
-
MDW
1h 55mnonstop
Southwest Logo
7:15 am - 12:30 pm
MDW
-
DCA
4h 15m
1 stop
$247Southwest
Sat, Aug 1 - Mon, Aug 3
American Airlines Logo
8:06 pm - 9:42 pm
DCA
-
ORD
2h 36mnonstop
American Airlines Logo
5:07 am - 10:50 am
ORD
-
DCA
4h 43m
1 stop
$247American Airlines
Thu, Sep 3 - Sat, Sep 5
JetBlue Logo
2:25 pm - 7:55 pm
DCA
-
ORD
6h 30m
1 stop
JetBlue Logo
1:49 pm - 9:50 pm
ORD
-
DCA
7h 01m
1 stop
$248JetBlue
Thu, Aug 27 - Sat, Aug 29
Delta Logo
5:47 pm - 10:36 pm
IAD
-
MDW
5h 49m
1 stop
Delta Logo
6:11 am - 1:43 pm
MDW
-
IAD
6h 32m
1 stop
$248Delta
Fri, Aug 14 - Tue, Aug 18
American Airlines Logo
11:56 am - 4:00 pm
DCA
-
ORD
5h 04m
1 stop
American Airlines Logo
9:56 am - 12:57 pm
ORD
-
DCA
2h 01mnonstop
$253American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$99
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 7% 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
Schererville
Chesterton
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 $514
Business Class flights to Chicagofrom $597
Premium Economy Class flights to Chicagofrom $747
Economy Class flights to Chicagofrom $233