$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 6/30. 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

Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
8:43 pm - 10:11 pm
DCA
-
ORD
2h 28mnonstop
American Airlines Logo
6:43 pm - 11:59 pm
ORD
-
DCA
4h 16m
1 stop
$247American Airlines
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
8:47 pm - 8:03 am
IAD
-
ORD
12h 16m
1 stop
Frontier Logo
6:55 am - 4:20 pm
ORD
-
IAD
8h 25m
1 stop
$247Frontier
Tue, Aug 4 - Wed, Aug 5
Southwest Logo
12:15 pm - 7:15 pm
RDU
-
MDW
8h 00m
1 stop
Southwest Logo
8:35 am - 11:35 am
MDW
-
RDU
2h 00mnonstop
$247Southwest
Wed, Jul 15 - Thu, Jul 16
Southwest Logo
9:30 pm - 10:35 pm
DCA
-
MDW
2h 05mnonstop
Southwest Logo
6:00 am - 8:45 am
MDW
-
DCA
1h 45mnonstop
$247Southwest
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
11:11 am - 10:11 pm
IAD
-
MDW
12h 00m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$247Frontier
Fri, Aug 21 - Mon, Aug 24
JetBlue Logo
2:00 pm - 7:25 pm
DCA
-
ORD
6h 25m
1 stop
JetBlue Logo
10:56 am - 7:56 pm
ORD
-
DCA
8h 00m
1 stop
$248JetBlue
Wed, Aug 26 - Wed, Sep 2
Multiple Airlines Logo
2:30 pm - 12:25 pm
RDU
-
ORD
22h 55m
2 stops
Multiple Airlines Logo
1:50 pm - 12:29 am
ORD
-
RDU
9h 39m
1 stop
$248Multiple Airlines
Tue, Aug 4 - Mon, Aug 10
Delta Logo
9:39 am - 1:08 pm
DCA
-
ORD
4h 29m
1 stop
Delta Logo
1:59 pm - 6:45 pm
ORD
-
DCA
3h 46m
1 stop
$251Delta
Wed, Sep 16 - Mon, Sep 21
Delta Logo
6:10 am - 9:07 am
DCA
-
MDW
3h 57m
1 stop
Delta Logo
5:10 pm - 11:43 pm
MDW
-
DCA
5h 33m
1 stop
$251Delta
Tue, Jul 7 - Mon, Jul 13
JetBlue Logo
2:25 pm - 7:31 pm
DCA
-
ORD
6h 06m
1 stop
JetBlue Logo
10:56 am - 6:00 pm
ORD
-
DCA
6h 04m
1 stop
$252JetBlue
Useful Info

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 with an average 6% increase in price.
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
Schererville
Munster
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 $499
Business Class flights to Chicagofrom $534
Premium Economy Class flights to Chicagofrom $551
Economy Class flights to Chicagofrom $233