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$37 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 8/21. 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
0 bags
Fri 6/21
Fri 6/28

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In the last 7 days travelers have searched 43,423,329 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

June

Cheapest flight

$37
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Raleigh 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.

See more FAQs

Prefer to fly non-stop from Virginia to Chicago?

Find which airlines fly direct from Virginia to Chicago, which days they fly and book direct flights.

Nonstop departures

Virginia to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Virginia

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Book cheap flights from Virginia to Chicago

Recent round-trip flight deals

6/4Tue
nonstopFrontier
2h 17mRDU-ORD
6/11Tue
nonstopFrontier
1h 58mORD-RDU
$58
6/5Wed
nonstopFrontier
2h 00mRDU-MDW
6/12Wed
nonstopFrontier
1h 53mMDW-RDU
$58
6/4Tue
1 stop
9h 53mRDU-ORD
6/11Tue
nonstop
1h 58mORD-RDU
$69
6/5Wed
1 stop
9h 17mRDU-ORD
6/11Tue
nonstop
1h 58mORD-RDU
$79
6/3Mon
1 stopSpirit Airlines
16h 50mRDU-ORD
6/5Wed
1 stopSpirit Airlines
11h 35mORD-RDU
$82
6/4Tue
1 stopSpirit Airlines
14h 26mRIC-ORD
6/11Tue
1 stopSpirit Airlines
13h 38mORD-RIC
$100
7/10Wed
nonstopAmerican Airlines
2h 19mRDU-ORD
7/10Wed
nonstopAmerican Airlines
2h 15mORD-RDU
$152
7/17Wed
nonstopUnited Airlines
2h 18mRDU-ORD
7/23Tue
nonstopUnited Airlines
2h 06mORD-RDU
$157
6/11Tue
nonstopAmerican Airlines
2h 14mDCA-ORD
6/11Tue
nonstopAmerican Airlines
1h 48mORD-DCA
$169
6/11Tue
nonstopUnited Airlines
2h 11mIAD-ORD
6/12Wed
nonstopUnited Airlines
2h 02mORD-IAD
$169

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Recent one-way flight deals

8/21Wed
nonstopFrontier
2h 01mRDU-MDW
$37
7/23Tue
nonstopFrontier
2h 15mRDU-ORD
$39
5/28Tue
1 stopSpirit Airlines
24h 52mRIC-ORD
$43
5/29Wed
1 stopSpirit Airlines
6h 24mRDU-ORD
$45
6/16Sun
1 stopSun Country Air
13h 10mIAD-ORD
$76
7/20Sat
nonstopUnited Airlines
2h 22mRDU-ORD
$79
6/25Tue
nonstopUnited Airlines
2h 10mIAD-ORD
$85
6/25Tue
nonstopAmerican Airlines
2h 14mDCA-ORD
$85
7/29Mon
1 stopSun Country Air
7h 53mRIC-ORD
$86
6/12Wed
nonstopAmerican Airlines
2h 20mRDU-ORD
$89

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Search by price

Last minute flights from Virginia to Chicago

Last minute flight, train and bus deals

5/26Sun
multi-stopSpirit Airlines
9h 53mRDU-ORD
5/30Thu
multi-stopSpirit Airlines
7h 36mORD-RDU
$208
5/26Sun
multi-stopFrontier
9h 46mRDU-MDW
5/29Wed
nonstopFrontier
2h 00mMDW-RDU
$225
5/26Sun
nonstop
2h 17mRDU-ORD
5/29Wed
multi-stop
7h 36mORD-RDU
$244
5/23Thu
nonstop
2h 17mRDU-ORD
5/28Tue
multi-stop
18h 55mORD-RDU
$280
5/25Sat
nonstopAmerican Airlines
2h 19mRDU-ORD
5/28Tue
nonstopAmerican Airlines
1h 53mORD-RDU
$315
5/25Sat
multi-stopDelta
4h 16mRDU-MDW
5/28Tue
multi-stopDelta
4h 48mMDW-RDU
$334
5/27Mon
nonstopUnited Airlines
2h 10mIAD-ORD
6/3Mon
nonstopUnited Airlines
2h 02mORD-IAD
$374
5/26Sun
nonstopUnited Airlines
2h 10mIAD-ORD
5/26Sun
multi-stopUnited Airlines
12h 43mORD-IAD
$403
5/23Thu
nonstopAmerican Airlines
2h 15mDCA-ORD
6/4Tue
multi-stopAmerican Airlines
3h 39mORD-DCA
$408
5/24Fri
multi-stopDelta
5h 56mRDU-MDW
6/5Wed
multi-stopDelta
6h 47mMDW-RDU
$443

Search by stops

Search by airline

Search by price