$55 Find Cheap Flights from Virginia to Chicago

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 1/8. 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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Everything you should know

Cheapest round-trip
$124
Overall average: $350
Frontier
Fri 12/5Thu 12/11
RDU - ORD • 1 stop
Cheapest non-stop
$128
Typical prices: $260-$423
Frontier
Tue 12/23Sun 12/28
RDU - ORD • Non-stop
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We hope you love your trip to Chicago!
Flight Deals
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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

Fri, Dec 5 - Thu, Dec 11
Frontier Logo
6:00 am - 2:40 pmRDU-ORD
9h 40m1 stop
Frontier Logo
11:44 am - 12:12 amORD-RDU
11h 28m1 stop
$124Frontier
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Thu, Dec 11 - Sun, Dec 14
Frontier Logo
1:03 pm - 10:12 pmRDU-MDW
10h 09m1 stop
Frontier Logo
6:15 am - 12:08 pmMDW-RDU
4h 53m1 stop
$124Frontier
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Mon, Nov 24 - Thu, Nov 27
Multiple Airlines Logo
4:05 pm - 5:30 pmRDU-ORD
2h 25mnonstop
Multiple Airlines Logo
10:12 am - 11:32 pmORD-RDU
12h 20m2 stops
$131Multiple Airlines
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Wed, Dec 10 - Wed, Dec 17
Southwest Logo
6:30 pm - 7:35 pmRDU-MDW
2h 05mnonstop
Southwest Logo
6:05 pm - 8:55 pmMDW-RDU
1h 50mnonstop
$139Southwest
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Tue, Nov 18 - Wed, Nov 19
JetBlue Logo
4:55 pm - 8:52 pmDCA-ORD
4h 57m1 stop
JetBlue Logo
6:45 am - 2:36 pmORD-DCA
6h 51m1 stop
$192JetBlue
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Fri, Feb 20 - Sun, Feb 22
Spirit Airlines Logo
6:45 am - 5:28 pmORF-ORD
11h 43m1 stop
Spirit Airlines Logo
12:44 pm - 9:50 pmORD-ORF
8h 06m1 stop
$192Spirit Airlines
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Tue, Nov 18 - Thu, Nov 20
JetBlue Logo
4:55 pm - 8:52 pmDCA-ORD
4h 57m1 stop
JetBlue Logo
8:20 am - 2:59 pmORD-DCA
5h 39m1 stop
$195JetBlue
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Mon, Dec 15 - Wed, Dec 17
Multiple Airlines Logo
8:38 am - 11:57 pmORF-ORD
16h 19m2 stops
Multiple Airlines Logo
1:34 pm - 10:03 pmORD-ORF
7h 29m1 stop
$195Multiple Airlines
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Mon, Dec 8 - Mon, Dec 15
Spirit Airlines Logo
8:38 am - 9:48 pmORF-ORD
14h 10m1 stop
Spirit Airlines Logo
9:14 pm - 7:16 pmORD-ORF
21h 02m2 stops
$199Spirit Airlines
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Wed, Dec 24 - Wed, Dec 31
Southwest Logo
3:20 pm - 4:30 pmDCA-MDW
2h 10mnonstop
Southwest Logo
8:10 pm - 10:55 pmMDW-DCA
1h 45mnonstop
$237Southwest
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$55
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Richmond to Chicago Midway 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
Schererville
Munster
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 $473
Business Class flights to Chicagofrom $902
Prem Econ Class flights to Chicagofrom $405
Economy Class flights to Chicagofrom $163