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Cheap flights from Virginia to Chicago 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 Virginia to Chicago departing on 1/8. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:11 am - 7:31 pmRDU-MDW
11h 20m1 stop
Frontier Logo
6:05 am - 6:19 pmMDW-RDU
11h 14m1 stop
$127Frontier
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Thu, Nov 20 - Sun, Nov 23
Frontier Logo
5:45 am - 1:59 pmRDU-MDW
9h 14m1 stop
Frontier Logo
3:52 pm - 4:44 pmMDW-RDU
23h 52m1 stop
$128Frontier
Find Deal
Sat, Dec 6 - Fri, Dec 12
Frontier Logo
12:53 pm - 11:25 pmRDU-MDW
11h 32m1 stop
Frontier Logo
2:12 pm - 12:10 amMDW-RDU
8h 58m1 stop
$129Frontier
Find Deal
Sun, Jan 11 - Sun, Jan 18
Frontier Logo
11:13 am - 7:42 pmRDU-MDW
9h 29m1 stop
Frontier Logo
6:15 am - 12:08 pmMDW-RDU
4h 53m1 stop
$138Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
5:10 pm - 6:15 pmRDU-MDW
2h 05mnonstop
Southwest Logo
9:50 am - 12:45 pmMDW-RDU
1h 55mnonstop
$139Southwest
Find Deal
Sat, Dec 6 - Sat, Dec 13
Southwest Logo
1:40 pm - 2:45 pmRDU-MDW
2h 05mnonstop
Southwest Logo
10:00 am - 1:00 pmMDW-RDU
2h 00mnonstop
$149Southwest
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Tue, Dec 2 - Tue, Dec 9
Delta Logo
5:29 am - 8:54 amRDU-MDW
4h 25m1 stop
Delta Logo
6:00 am - 11:37 amMDW-RDU
4h 37m1 stop
$178Delta
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Tue, Dec 2 - Tue, Dec 9
Multiple Airlines Logo
3:00 pm - 6:46 pmIAD-MDW
4h 46m1 stop
Multiple Airlines Logo
5:30 pm - 7:45 amMDW-IAD
13h 15m1 stop
$182Multiple Airlines
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Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
8:39 pm - 11:42 amRDU-MDW
16h 03m1 stop
Multiple Airlines Logo
5:57 pm - 11:18 amMDW-RDU
16h 21m1 stop
$186Multiple Airlines
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Sat, Nov 22 - Wed, Nov 26
Delta Logo
9:57 am - 12:34 pmRDU-MDW
3h 37m1 stop
Delta Logo
1:14 pm - 5:40 pmMDW-RDU
3h 26m1 stop
$187Delta
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Thu, Dec 11 - Sat, Dec 13

Southwest flights from Virginia to Chicago Midway Airport

Our best Southwest deals on Virginia to Chicago Midway Airport flight tickets
Southwest
Dec 6
RDU5:10 pmRaleigh-Durham
2h 05m
MDW6:15 pmChicago Midway
Dec 13
MDW9:50 amChicago Midway
1h 55m
RDU12:45 pmRaleigh-Durham
$139
Find similar
Southwest
Dec 2
RDU1:40 pmRaleigh-Durham
2h 05m
MDW2:45 pmChicago Midway
Dec 9
MDW10:00 amChicago Midway
2h 00m
RDU1:00 pmRaleigh-Durham
$149
Find similar
Southwest
Dec 6
RDU5:10 pmRaleigh-Durham
2h 05m
MDW6:15 pmChicago Midway
Dec 7
MDW7:30 pmChicago Midway
1h 50m
RDU10:20 pmRaleigh-Durham
$158
Find similar

Frontier flights from Virginia to Chicago Midway Airport

Our best Frontier deals on Virginia to Chicago Midway Airport flight tickets
Frontier
Nov 20
RDU9:11 amRaleigh-Durham
11h 20m
1 stop
MDW7:31 pmChicago Midway
Nov 23
MDW6:05 amChicago Midway
11h 14m
1 stop
RDU6:19 pmRaleigh-Durham
$127
Find similar
Frontier
Dec 6
RDU5:45 amRaleigh-Durham
9h 14m
1 stop
MDW1:59 pmChicago Midway
Dec 12
MDW3:52 pmChicago Midway
23h 52m
1 stop
RDU4:44 pmRaleigh-Durham
$128
Find similar
Frontier
Jan 11
RDU12:53 pmRaleigh-Durham
11h 32m
1 stop
MDW11:25 pmChicago Midway
Jan 18
MDW2:12 pmChicago Midway
8h 58m
1 stop
RDU12:10 amRaleigh-Durham
$129
Find similar

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 November 6, 2025.
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

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 11/20

9:11 am-7:31 pm

1 stop11h 20m

Chicago Midway

Sun 11/23

6:05 am-6:19 pm

1 stop11h 14m

$127

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:45 am-1:59 pm

1 stop9h 14m

Chicago Midway

Fri 12/12

3:52 pm-4:44 pm

1 stop23h 52m

$128

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sun 1/11

12:53 pm-11:25 pm

1 stop11h 32m

Chicago Midway

Sun 1/18

2:12 pm-12:10 am

1 stop8h 58m

$129

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Fri 12/5

11:13 am-7:42 pm

1 stop9h 29m

Chicago Midway

Sun 12/7

6:15 am-12:08 pm

1 stop4h 53m

$138

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 12/6

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Sat 12/13

9:50 am-12:45 pm

Nonstop1h 55m

$139

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 12/2

1:40 pm-2:45 pm

Nonstop2h 05m

Chicago Midway

Tue 12/9

10:00 am-1:00 pm

Nonstop2h 00m

$149

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Tue 12/2

5:29 am-8:54 am

1 stop4h 25m

Chicago Midway

Tue 12/9

6:00 am-11:37 am

1 stop4h 37m

$178

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 11/21

3:00 pm-6:46 pm

1 stop4h 46m

Chicago Midway

Sun 11/23

5:30 pm-7:45 am

1 stop13h 15m

$182

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 11/22

8:39 pm-11:42 am

1 stop16h 03m

Chicago Midway

Wed 11/26

5:57 pm-11:18 am

1 stop16h 21m

$186

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 12/11

9:57 am-12:34 pm

1 stop3h 37m

Chicago Midway

Sat 12/13

1:14 pm-5:40 pm

1 stop3h 26m

$187

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Virginia, with most prices found around $261. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Virginia during the month April is also very affordable. Most momondo users find prices during this month for around $335.

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 $428. 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, Saturday 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 $520.

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 $390 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $486. 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 Richmond Byrd Intl to Chicago Midway for the best Virginia - Chicago Midway flight prices

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

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

You could potentially save up to 44% on your flight if you consider stops on a Virginia to Chicago Midway Airport flight.

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

$137

Fastest flight time

2h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Virginia in the past 72 hours is $137. The best round-trip flight deal from Virginia to Chicago Midway Airport found on momondo in the last 72 hours is $386.
The fastest flight from Virginia to Chicago Midway Airport takes 2h 00m
Direct flights go from Virginia to Chicago Midway Airport every day.
Search flight deals

  • 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
DeltaPriceFrom $228Free CancellationRating
7.9
8,001 reviews
Search Delta flights
SouthwestPriceFrom $229Free CancellationRating
8.0
4,241 reviews
Search Southwest flights

Traveling to a place near Chicago?

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