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Cheap flights from Virginia to Chicago from $64

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 6/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Virginia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:48 pm - 11:09 am
RDU
-
MDW
18h 21m
2 stops
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
$201Frontier
Sun, May 31 - Tue, Jun 2
Multiple Airlines Logo
10:03 pm - 10:02 pm
RDU
-
MDW
24h 59m
2 stops
Multiple Airlines Logo
6:00 am - 12:29 am
MDW
-
RDU
17h 29m
1 stop
$203Multiple Airlines
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
6:15 am - 11:07 am
RDU
-
MDW
5h 52m
1 stop
Frontier Logo
12:11 pm - 12:25 am
MDW
-
RDU
11h 14m
1 stop
$204Frontier
Tue, Jul 14 - Sat, Jul 18
Frontier Logo
11:56 am - 10:02 pm
RDU
-
MDW
11h 06m
1 stop
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
$205Frontier
Sat, Jun 6 - Sun, Jun 14
Frontier Logo
12:23 pm - 10:02 pm
RDU
-
MDW
10h 39m
1 stop
Frontier Logo
6:00 am - 12:04 pm
MDW
-
RDU
5h 04m
1 stop
$206Frontier
Sat, May 16 - Tue, May 19
Multiple Airlines Logo
12:10 pm - 10:11 pm
RDU
-
MDW
11h 01m
1 stop
Multiple Airlines Logo
8:20 pm - 9:19 am
MDW
-
RDU
35h 59m
2 stops
$212Multiple Airlines
Wed, Jun 10 - Mon, Jun 15
Delta Logo
6:08 am - 10:00 am
IAD
-
MDW
4h 52m
1 stop
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
$228Delta
Tue, May 26 - Thu, May 28
Delta Logo
6:00 am - 10:00 am
DCA
-
MDW
5h 00m
1 stop
Delta Logo
10:45 am - 6:28 pm
MDW
-
DCA
6h 43m
1 stop
$228Delta
Wed, May 27 - Sat, May 30
Southwest Logo
9:05 am - 3:45 pm
DCA
-
MDW
7h 40m
2 stops
Southwest Logo
6:35 pm - 9:30 pm
MDW
-
DCA
1h 55mnonstop
$233Southwest
Wed, May 27 - Sat, May 30
Southwest Logo
2:40 pm - 9:45 pm
DCA
-
MDW
8h 05m
2 stops
Southwest Logo
7:45 am - 5:35 pm
MDW
-
DCA
8h 50m
2 stops
$238Southwest
Wed, May 27 - Sat, May 30

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Southwest flights from Virginia to Chicago Midway Airport

Our best Southwest deals on Virginia to Chicago Midway Airport flight tickets
Southwest
May 27
DCA2:40 pmWashington, D.C. Reagan-National
8h 05m
2 stops
MDW9:45 pmChicago Midway
Jun 4
MDW11:15 amChicago Midway
1h 45m
DCA2:00 pmWashington, D.C. Reagan-National
$233
Southwest
Jun 2
RDU6:40 pmRaleigh-Durham
2h 00m
MDW7:40 pmChicago Midway
Jun 3
MDW6:05 pmChicago Midway
1h 50m
RDU8:55 pmRaleigh-Durham
$237
Southwest
Jun 6
DCA6:10 amWashington, D.C. Reagan-National
2h 00m
MDW7:10 amChicago Midway
Jun 6
MDW12:55 pmChicago Midway
1h 55m
DCA3:50 pmWashington, D.C. Reagan-National
$239

Delta flights from Virginia to Chicago Midway Airport

Our best Delta deals on Virginia to Chicago Midway Airport flight tickets
Delta
May 27
DCA6:00 amWashington, D.C. Reagan-National
5h 00m
1 stop
MDW10:00 amChicago Midway
May 30
MDW10:45 amChicago Midway
6h 43m
1 stop
DCA6:28 pmWashington, D.C. Reagan-National
$228
Delta
May 27
DCA6:05 amWashington, D.C. Reagan-National
3h 38m
1 stop
MDW8:43 amChicago Midway
Jun 4
MDW5:15 pmChicago Midway
5h 29m
1 stop
DCA11:44 pmWashington, D.C. Reagan-National
$238
Delta
Jun 10
IAD12:37 pmWashington, D.C. Dulles Intl
4h 39m
1 stop
MDW4:16 pmChicago Midway
Jun 17
MDW11:05 amChicago Midway
4h 42m
1 stop
IAD4:47 pmWashington, D.C. Dulles Intl
$248

momondo Fare Finder

 
Customize your flight search to find flights from Virginia to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Virginia to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 5/31

5:48 pm-11:09 am

2 stops18h 21m

Chicago Midway

Tue 6/2

6:00 am-11:59 am

1 stop4h 59m

$201

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/3

10:03 pm-10:02 pm

2 stops24h 59m

Chicago Midway

Tue 6/9

6:00 am-12:29 am

1 stop17h 29m

$203

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 7/14

6:15 am-11:07 am

1 stop5h 52m

Chicago Midway

Sat 7/18

12:11 pm-12:25 am

1 stop11h 14m

$204

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 6/6

11:56 am-10:02 pm

1 stop11h 06m

Chicago Midway

Sun 6/14

6:00 am-11:59 am

1 stop4h 59m

$205

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 5/16

12:23 pm-10:02 pm

1 stop10h 39m

Chicago Midway

Tue 5/19

6:00 am-12:04 pm

1 stop5h 04m

$206

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 6/10

12:10 pm-10:11 pm

1 stop11h 01m

Chicago Midway

Mon 6/15

8:20 pm-9:19 am

2 stops35h 59m

$212
Quickest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 5/26

6:08 am-10:00 am

1 stop4h 52m

Chicago Midway

Thu 5/28

6:36 pm-10:56 pm

1 stop3h 20m

$228

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/27

6:00 am-10:00 am

1 stop5h 00m

Chicago Midway

Sat 5/30

10:45 am-6:28 pm

1 stop6h 43m

$228

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/27

9:05 am-3:45 pm

2 stops7h 40m

Chicago Midway

Sat 5/30

6:35 pm-9:30 pm

Nonstop1h 55m

$233

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/27

2:40 pm-9:45 pm

2 stops8h 05m

Chicago Midway

Sat 5/30

7:45 am-5:35 pm

2 stops8h 50m

$238

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Virginia to Chicago Midway Airport

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 Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Virginia, with most prices found around $152. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Virginia during the month October is also very affordable. Most momondo users find prices during this month for around $154.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Virginia. The lowest ticket price found for a Tuesday departure recently was $434. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Virginia because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $496.

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

Flying to Chicago Midway Airport from Virginia in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $395 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $475. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Virginia to Chicago Midway flight route?

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

Can stopping save me money on Virginia to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Virginia to Chicago Midway Airport.

Cheap Virginia to Chicago Midway Airport flight deals and tips

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

Best Price Found

$193

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Virginia in the past 72 hours is $193. The best round-trip flight deal from Virginia to Chicago Midway Airport found on momondo in the last 72 hours is $414.
The fastest flight from Virginia to Chicago Midway Airport takes 1h 50m
Direct flights go from Virginia to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Virginia to Chicago Midway Airport

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

    Prices for flights from Virginia to Chicago Midway Airport are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Virginia to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport 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 Midway Airport. 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 Midway Airport?

Best airlines flying from Virginia to Chicago Midway Airport

Compare and see reviews for airlines that fly from Virginia to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $154Free CancellationRating
5.6
2,964 reviews
Search Frontier flights
SouthwestPriceFrom $178Free CancellationRating
7.9
4,305 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,458 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Virginia to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

momondo does allow users to show only those flights to Chicago from Virginia which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Virginia to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Virginia and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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