$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 7/15. 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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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
3:41 pm - 5:14 pm
DCA
-
ORD
2h 33mnonstop
American Airlines Logo
7:03 am - 10:00 am
ORD
-
DCA
1h 57mnonstop
$247American Airlines
Tue, Jul 28 - Wed, Jul 29
Frontier Logo
9:50 am - 5:37 am
IAD
-
ORD
20h 47m
1 stop
Frontier Logo
1:50 pm - 10:55 pm
ORD
-
IAD
8h 05m
1 stop
$247Frontier
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
7:00 pm - 8:00 pm
RDU
-
MDW
2h 00mnonstop
Southwest Logo
2:40 pm - 9:55 pm
MDW
-
RDU
6h 15m
1 stop
$247Southwest
Wed, Jul 15 - Thu, Jul 16
Southwest Logo
7:55 pm - 11:15 pm
DCA
-
MDW
4h 20m
1 stop
Southwest Logo
6:00 am - 8:45 am
MDW
-
DCA
1h 45mnonstop
$247Southwest
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
11:13 am - 4:46 pm
RDU
-
ORD
6h 33m
1 stop
American Airlines Logo
8:18 am - 11:38 am
ORD
-
RDU
2h 20mnonstop
$247American Airlines
Thu, Sep 3 - Thu, Sep 10
JetBlue Logo
1:25 pm - 7:25 pm
DCA
-
ORD
7h 00m
1 stop
JetBlue Logo
2:15 pm - 9:00 pm
ORD
-
DCA
5h 45m
1 stop
$248JetBlue
Tue, Jun 30 - Tue, Jul 7
Frontier Logo
8:57 pm - 8:03 am
IAD
-
ORD
12h 06m
1 stop
Frontier Logo
8:05 am - 7:38 pm
ORD
-
IAD
10h 33m
1 stop
$248Frontier
Fri, Aug 21 - Sat, Sep 5
United Airlines Logo
6:30 am - 7:44 am
DCA
-
ORD
2h 14mnonstop
United Airlines Logo
3:00 pm - 6:09 pm
ORD
-
DCA
2h 09mnonstop
$253United Airlines
Fri, Aug 21 - Sat, Sep 5
United Airlines Logo
10:27 pm - 11:40 pm
IAD
-
ORD
2h 13mnonstop
United Airlines Logo
6:15 pm - 9:20 pm
ORD
-
IAD
2h 05mnonstop
$253United Airlines
Tue, Jul 7 - Wed, Jul 8
JetBlue Logo
9:38 am - 5:34 pm
RIC
-
ORD
8h 56m
2 stops
JetBlue Logo
10:56 am - 5:25 pm
ORD
-
RIC
5h 29m
1 stop
$321JetBlue
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 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
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