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Cheap flights from Virginia to Chicago from $39

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Virginia to Chicago departing on 4/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Virginia to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Virginia to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Virginia to Chicago.

Cheap last minute flights

Planning a quick getaway from Virginia to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Virginia to Chicago

Find recent round-trip train or bus tickets from Virginia to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:20 pm - 12:17 amRDU-MDW
7h 57m1 stop
7:15 am - 4:20 pmMDW-RDU
8h 05m1 stop
$106Frontier
Find Deal
Mon, Jan 27 - Thu, Jan 30
3:07 pm - 10:27 pmRDU-ORD
8h 20m1 stop
7:25 am - 4:20 pmORD-RDU
7h 55m1 stop
$107Frontier
Find Deal
Mon, Jan 20 - Thu, Jan 23
5:30 am - 4:06 pmRDU-ORD
11h 36m1 stop
9:35 am - 7:52 amORD-RDU
21h 17m1 stop
Tue, Dec 10 - Thu, Dec 12
12:10 pm - 7:51 pmRDU-ORD
8h 41m1 stop
10:22 pm - 6:59 amORD-RDU
7h 37m1 stop
Fri, Dec 20 - Wed, Dec 25
5:15 am - 11:04 amRDU-ORD
6h 49m1 stop
5:11 am - 1:21 pmORD-RDU
7h 10m1 stop
$161Spirit Airlines
Find Deal
Wed, Jan 8 - Sun, Jan 12
7:00 am - 2:32 pmRIC-ORD
8h 32m1 stop
7:10 am - 6:23 pmORD-RIC
10h 13m1 stop
$179Spirit Airlines
Find Deal
Thu, Feb 6 - Mon, Feb 24
10:41 am - 5:53 pmRIC-ORD
8h 12m1 stop
11:00 am - 6:20 pmORD-RIC
6h 20m1 stop
$180JetBlue
Find Deal
Sun, Jan 12 - Sun, Jan 19
10:45 am - 5:59 pmDCA-ORD
8h 14m1 stop
7:00 am - 5:00 pmORD-DCA
9h 00m1 stop
$182JetBlue
Find Deal
Tue, Jan 7 - Sat, Jan 11
6:15 am - 10:53 amGSO-ORD
5h 38m1 stop
11:05 am - 4:30 pmORD-GSO
4h 25m1 stop
$228Delta
Find Deal
Tue, Jan 14 - Tue, Jan 21
6:00 am - 9:09 amDCA-ORD
4h 09m1 stop
6:45 am - 12:00 pmORD-DCA
4h 15m1 stop
$248Delta
Find Deal
Sat, Jan 4 - Mon, Jan 6
10:59 am - 12:16 pmRDU-ORD
2h 17mnonstop
$39Frontier
Find Deal
Tue, Apr 1
5:20 pm - 12:44 amRDU-ORD
8h 24m1 stop
$53Frontier
Find Deal
Mon, Mar 3
10:20 am - 8:13 pmRIC-ORD
10h 53m1 stop
$79Spirit Airlines
Find Deal
Wed, Jan 15
5:15 am - 11:04 amRDU-ORD
6h 49m1 stop
$79Spirit Airlines
Find Deal
Wed, Jan 8
11:15 am - 5:59 pmRIC-ORD
7h 44m1 stop
$90JetBlue
Find Deal
Sun, Jan 12
10:45 am - 5:59 pmDCA-ORD
8h 14m1 stop
$91JetBlue
Find Deal
Sat, Jan 25
9:43 am - 11:03 amDCA-ORD
2h 20mnonstop
$105American Airlines
Find Deal
Wed, Dec 11
7:41 am - 8:55 amGSO-ORD
2h 14mnonstop
$105American Airlines
Find Deal
Wed, Feb 26
3:40 pm - 7:47 amRIC-ORD
17h 07m1 stop
Mon, Jan 6
3:32 pm - 7:40 amRDU-ORD
17h 08m1 stop
Sat, May 10
12:10 pm - 2:31 pmRDU-ORD
27h 21m1 stop
5:00 am - 5:36 pmORD-RDU
11h 36m1 stop
$312Spirit Airlines
Find Deal
Mon, Dec 2 - Sat, Dec 14
7:00 am - 1:40 pmDCA-MDW
7h 40m1 stop
7:15 am - 4:59 pmMDW-DCA
8h 44m1 stop
$328Frontier
Find Deal
Mon, Dec 2 - Fri, Dec 6
12:10 pm - 9:20 amRDU-ORD
22h 10m1 stop
10:59 am - 11:50 amORD-RDU
23h 51m1 stop
Mon, Dec 2 - Fri, Dec 13
2:54 pm - 7:26 pmDCA-ORD
5h 32m1 stop
8:28 pm - 11:24 pmORD-DCA
1h 56mnonstop
$373American Airlines
Find Deal
Fri, Nov 29 - Fri, Nov 29
4:15 pm - 9:20 amRDU-ORD
18h 05m2 stops
5:00 am - 5:36 pmORD-RDU
11h 36m1 stop
Mon, Dec 2 - Sat, Dec 14
5:15 pm - 6:55 pmIAD-ORD
26h 40m1 stop
9:10 pm - 11:59 pmORD-IAD
1h 49mnonstop
$419United Airlines
Find Deal
Thu, Nov 28 - Fri, Nov 29
9:25 am - 10:30 amDCA-MDW
2h 05mnonstop
11:30 am - 2:15 pmMDW-DCA
1h 45mnonstop
$435Southwest
Find Deal
Fri, Nov 29 - Thu, Dec 19
10:55 am - 3:10 pmDCA-MDW
5h 15m1 stop
8:10 pm - 10:55 pmMDW-DCA
1h 45mnonstop
$444Southwest
Find Deal
Fri, Nov 29 - Thu, Dec 19
11:59 am - 1:12 pmDCA-ORD
2h 13mnonstop
12:01 pm - 2:55 pmORD-DCA
1h 54mnonstop
$469American Airlines
Find Deal
Fri, Nov 29 - Thu, Dec 19
1:05 pm - 2:19 pmIAD-ORD
2h 14mnonstop
6:08 pm - 9:00 pmORD-IAD
1h 52mnonstop
$469United Airlines
Find Deal
Mon, Dec 2 - Tue, Dec 31
5:59 pm - 7:24 pmDCA-ORD
2h 25mnonstop
6:05 am - 9:00 amORD-DCA
1h 55mnonstop
$219American Airlines
Find Deal
Tue, Dec 17 - Sat, Dec 21
6:30 am - 7:48 amDCA-ORD
2h 18mnonstop
9:05 pm - 11:59 pmORD-DCA
1h 54mnonstop
$229United Airlines
Find Deal
Sun, Dec 29 - Mon, Dec 30
7:00 am - 8:20 amIAD-ORD
2h 20mnonstop
9:05 pm - 11:59 pmORD-IAD
1h 54mnonstop
$229United Airlines
Find Deal
Thu, Dec 19 - Sun, Dec 22
2:55 pm - 4:05 pmDCA-MDW
2h 10mnonstop
3:15 pm - 6:00 pmMDW-DCA
1h 45mnonstop
$230Southwest
Find Deal
Fri, Jan 10 - Mon, Jan 13
6:42 am - 8:03 amDCA-ORD
2h 21mnonstop
8:05 am - 10:56 amORD-DCA
1h 51mnonstop
$230American Airlines
Find Deal
Fri, Jan 10 - Mon, Jan 13
11:59 am - 1:17 pmDCA-ORD
2h 18mnonstop
6:00 am - 8:55 amORD-DCA
1h 55mnonstop
$231American Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
11:59 am - 1:21 pmDCA-ORD
2h 22mnonstop
1:42 pm - 4:29 pmORD-DCA
1h 47mnonstop
$243American Airlines
Find Deal
Tue, Dec 10 - Tue, Dec 17
5:00 pm - 6:23 pmGSO-ORD
2h 23mnonstop
5:55 pm - 8:54 pmORD-GSO
1h 59mnonstop
$244United Airlines
Find Deal
Sat, Jan 11 - Mon, Jan 13
6:55 am - 8:05 amDCA-MDW
2h 10mnonstop
8:10 pm - 10:55 pmMDW-DCA
1h 45mnonstop
$264Southwest
Find Deal
Thu, Dec 19 - Mon, Dec 23
10:59 am - 12:16 pmRDU-ORD
2h 17mnonstop
7:00 am - 9:59 amORD-RDU
1h 59mnonstop
$319Frontier
Find Deal
Thu, Apr 3 - Sun, Apr 6

Spirit Airlines flights from Virginia to Chicago

Our best Spirit Airlines deals on Virginia to Chicago flight tickets
Spirit Airlines
Jan 8
RDU5:15 amRaleigh-Durham
6h 49m
1 stop
ORD11:04 amChicago O'Hare Intl
Jan 12
ORD5:11 amChicago O'Hare Intl
7h 10m
1 stop
RDU1:21 pmRaleigh-Durham
Spirit Airlines
Feb 6
RIC7:00 amRichmond Byrd Intl
8h 32m
1 stop
ORD2:32 pmChicago O'Hare Intl
Feb 24
ORD7:10 amChicago O'Hare Intl
10h 13m
1 stop
RIC6:23 pmRichmond Byrd Intl
Spirit Airlines
Dec 7
RDU5:30 amRaleigh-Durham
11h 36m
1 stop
ORD4:06 pmChicago O'Hare Intl
Dec 10
ORD9:58 amChicago O'Hare Intl
11h 38m
1 stop
RDU10:36 pmRaleigh-Durham

Frontier flights from Virginia to Chicago

Our best Frontier deals on Virginia to Chicago flight tickets
Frontier
Jan 27
RDU5:20 pmRaleigh-Durham
7h 57m
1 stop
MDW12:17 amChicago Midway
Jan 30
MDW7:15 amChicago Midway
8h 05m
1 stop
RDU4:20 pmRaleigh-Durham
Frontier
Jan 20
RDU3:07 pmRaleigh-Durham
8h 20m
1 stop
ORD10:27 pmChicago O'Hare Intl
Jan 23
ORD7:25 amChicago O'Hare Intl
7h 55m
1 stop
RDU4:20 pmRaleigh-Durham
Frontier
Jan 30
DCA7:00 amWashington, D.C. Reagan-National
8h 02m
1 stop
ORD2:02 pmChicago O'Hare Intl
Feb 3
ORD7:50 amChicago O'Hare Intl
13h 09m
1 stop
DCA9:59 pmWashington, D.C. Reagan-National

See travel insights to Chicago from

How to get the cheapest flight ticket from Virginia to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $314. If you’re not able to fly to Chicago in January, then March is your next best option. Flight prices from Virginia to Chicago during March average around $320.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $338. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Virginia to Chicago for around $391.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Virginia to Chicago during this time can be as low as $344. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $405.

What is the cheapest Virginia to Chicago flight route?

Fly from Norfolk to Chicago Midway for the best Virginia - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Virginia is 36 days out, which is when prices tend to be around $355. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $185.

What cabin class options are available on Virginia to Chicago flights?

There are 4 cabin classes available to choose from on Virginia to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Virginia to Chicago flights?

You could potentially save up to 35% on your flight if you consider stops on a Virginia to Chicago flight.

Cheap Virginia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Virginia to Chicago

Best Price Found

$39

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Virginia in the past 72 hours is $39. The best round-trip flight deal from Virginia to Chicago found on momondo in the last 72 hours is $106.
The fastest flight from Virginia to Chicago takes 2h 00m
Direct flights go from Virginia to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • When did momondo last update prices for flights from Virginia to Chicago?

    Prices for flights from Virginia to Chicago refresh daily.

  • How many operators does momondo search for flights from Virginia to Chicago?

  • How old do you have to be to fly from Virginia to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Virginia to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Virginia to Chicago?


Best airlines flying from Virginia to Chicago

Compare and see reviews for airlines that fly from Virginia to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $105Free CancellationRating
6.3
8,172 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $148Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $175Free CancellationRating
8.0
8,730 reviews
Search Delta flights
United AirlinesPriceFrom $190Free CancellationRating
7.4
9,146 reviews
Search United Airlines flights
SouthwestPriceFrom $257Free CancellationRating
8.1
4,979 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Virginia to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Virginia to Chicago for you.

Can I find flights from Virginia to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Virginia on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Virginia to Chicago?

momondo helps you find the best flight between Virginia and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Virginia to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Virginia to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago