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Cheap flights from Chicago Midway Airport to Virginia from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Virginia departing on 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Virginia

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:36 am - 6:17 pmMDW-RDU
5h 41m1 stop
Frontier Logo
8:31 am - 2:33 pmRDU-MDW
7h 02m1 stop
$110Frontier
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Sat, Nov 15 - Mon, Nov 17
Frontier Logo
8:05 am - 7:09 pmMDW-RDU
10h 04m1 stop
Frontier Logo
1:03 pm - 6:12 pmRDU-MDW
6h 09m1 stop
$124Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
11:36 am - 6:17 pmMDW-RDU
5h 41m1 stop
Frontier Logo
9:35 pm - 8:32 amRDU-MDW
11h 57m1 stop
$128Frontier
Find Deal
Sat, Nov 15 - Sun, Nov 16
Southwest Logo
10:00 am - 1:00 pmMDW-RDU
2h 00mnonstop
Southwest Logo
1:40 pm - 2:45 pmRDU-MDW
2h 05mnonstop
$139Southwest
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Tue, Dec 2 - Tue, Dec 9
Frontier Logo
6:15 am - 12:08 pmMDW-RDU
4h 53m1 stop
Frontier Logo
1:03 pm - 6:12 pmRDU-MDW
6h 09m1 stop
$142Frontier
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Sun, Dec 7 - Sun, Dec 14
Southwest Logo
6:05 pm - 8:55 pmMDW-RDU
1h 50mnonstop
Southwest Logo
1:50 pm - 8:15 pmRDU-MDW
7h 25m1 stop
$149Southwest
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Wed, Dec 24 - Wed, Dec 31
Multiple Airlines Logo
6:15 am - 4:24 pmMDW-IAD
9h 09m1 stop
Multiple Airlines Logo
9:20 pm - 10:12 pmIAD-MDW
25h 52m2 stops
$171Multiple Airlines
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Fri, Dec 5 - Sun, Dec 7
Multiple Airlines Logo
6:15 am - 4:24 pmMDW-IAD
9h 09m1 stop
Multiple Airlines Logo
9:20 pm - 10:12 pmIAD-MDW
25h 52m2 stops
$177Multiple Airlines
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Fri, Dec 5 - Sun, Dec 7
Delta Logo
9:34 am - 4:20 pmMDW-RDU
5h 46m1 stop
Delta Logo
1:00 pm - 4:31 pmRDU-MDW
4h 31m1 stop
$187Delta
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Wed, Jan 14 - Sat, Jan 17
Delta Logo
1:14 pm - 5:40 pmMDW-RDU
3h 26m1 stop
Delta Logo
5:29 am - 8:54 amRDU-MDW
4h 25m1 stop
$197Delta
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Fri, Dec 5 - Sun, Dec 7

Southwest flights from Chicago Midway Airport to Virginia

Our best Southwest deals on Chicago Midway Airport to Virginia flight tickets
Southwest
Dec 2
MDW10:00 amChicago Midway
2h 00m
RDU1:00 pmRaleigh-Durham
Dec 9
RDU1:40 pmRaleigh-Durham
2h 05m
MDW2:45 pmChicago Midway
$139
Find similar
Southwest
Dec 24
MDW6:05 pmChicago Midway
1h 50m
RDU8:55 pmRaleigh-Durham
Dec 31
RDU1:50 pmRaleigh-Durham
7h 25m
1 stop
MDW8:15 pmChicago Midway
$149
Find similar
Southwest
Jan 17
MDW9:45 amChicago Midway
1h 50m
RDU12:35 pmRaleigh-Durham
Jan 21
RDU6:00 amRaleigh-Durham
2h 15m
MDW7:15 amChicago Midway
$158
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Frontier flights from Chicago Midway Airport to Virginia

Our best Frontier deals on Chicago Midway Airport to Virginia flight tickets
Frontier
Nov 15
MDW11:36 amChicago Midway
5h 41m
1 stop
RDU6:17 pmRaleigh-Durham
Nov 17
RDU8:31 amRaleigh-Durham
7h 02m
1 stop
MDW2:33 pmChicago Midway
$110
Find similar
Frontier
Dec 4
MDW8:05 amChicago Midway
10h 04m
1 stop
RDU7:09 pmRaleigh-Durham
Dec 7
RDU1:03 pmRaleigh-Durham
6h 09m
1 stop
MDW6:12 pmChicago Midway
$124
Find similar
Frontier
Nov 15
MDW11:36 amChicago Midway
5h 41m
1 stop
RDU6:17 pmRaleigh-Durham
Nov 16
RDU9:35 pmRaleigh-Durham
11h 57m
1 stop
MDW8:32 amChicago Midway
$128
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Virginia 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 November 3, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Virginia that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Sat 11/15

11:36 am-6:17 pm

1 stop5h 41m

Raleigh-Durham

Mon 11/17

8:31 am-2:33 pm

1 stop7h 02m

$110

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Thu 12/4

8:05 am-7:09 pm

1 stop10h 04m

Raleigh-Durham

Sun 12/7

1:03 pm-6:12 pm

1 stop6h 09m

$124

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Sat 11/15

11:36 am-6:17 pm

1 stop5h 41m

Raleigh-Durham

Sun 11/16

9:35 pm-8:32 am

1 stop11h 57m

$128

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Tue 12/2

10:00 am-1:00 pm

Nonstop2h 00m

Raleigh-Durham

Tue 12/9

1:40 pm-2:45 pm

Nonstop2h 05m

$139

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Sun 12/7

6:15 am-12:08 pm

1 stop4h 53m

Raleigh-Durham

Sun 12/14

1:03 pm-6:12 pm

1 stop6h 09m

$142

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Wed 12/24

6:05 pm-8:55 pm

Nonstop1h 50m

Raleigh-Durham

Wed 12/31

1:50 pm-8:15 pm

1 stop7h 25m

$149

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 12/5

6:15 am-4:24 pm

1 stop9h 09m

Washington, D.C. Dulles Intl

Sun 12/7

9:20 pm-10:12 pm

2 stops25h 52m

$171

ChicagoWashington, D.C.

MDW - IAD

MDWIAD

Chicago Midway

Fri 12/5

6:15 am-4:24 pm

1 stop9h 09m

Washington, D.C. Dulles Intl

Sun 12/7

9:20 pm-10:12 pm

2 stops25h 52m

$177

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Wed 1/14

9:34 am-4:20 pm

1 stop5h 46m

Raleigh-Durham

Sat 1/17

1:00 pm-4:31 pm

1 stop4h 31m

$187

ChicagoRaleigh

MDW - RDU

MDWRDU

Chicago Midway

Fri 12/5

1:14 pm-5:40 pm

1 stop3h 26m

Raleigh-Durham

Sun 12/7

5:29 am-8:54 am

1 stop4h 25m

$197

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 Virginia from

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

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 day to depart on your flight to Virginia?

On average, the least expensive day to fly to Virginia from Chicago Midway Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $350. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Virginia on Saturday is $422.

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

Our data shows that the cheapest Chicago Midway Airport to Virginia flights are usually those with departure times in the afternoon. Our users have found flights to Virginia in the afternoon for as low as $371. At noon is when there is more demand to fly to Virginia, so prices are often more expensive at around $416 per ticket.

What is the cheapest Chicago Midway to Virginia flight route?

Fly from Chicago Midway to Richmond Byrd Intl for the best Chicago Midway - Virginia flight prices

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

There is only 1 cabin class available to choose from on Chicago Midway to Virginia 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 Chicago Midway Airport to Virginia flights?

You could potentially save up to 14% on your flight if you consider stops on a Chicago Midway Airport to Virginia flight.

Cheap Chicago Midway Airport to Virginia flight deals and tips

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

Fastest flight time

1h 45m

Direct flights

Every day

Airports in Virginia

2 airports
The fastest flight from Chicago Midway Airport to Virginia takes 1h 45m
Direct flights go from Chicago Midway Airport to Virginia every day.
There are 2 airports near Virginia: Raleigh-Durham (RDU), Washington, D.C. Reagan-National (DCA)
Search flight deals

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

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

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

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

    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 Chicago Midway Airport to Virginia.

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

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

Best airlines flying from Chicago Midway Airport to Virginia

Compare and see reviews for airlines that fly from Chicago Midway Airport to Virginia with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $230Free CancellationRating
8.0
4,238 reviews
Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Virginia from Chicago.

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

Yes. momondo allows you to filter the results for Chicago to Virginia flights to just show those with flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Virginia.

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

Yes. momondo can track prices for Chicago to Virginia flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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