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Cheap flights from Virginia to Chicago from $70

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 9/24. 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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Cheap round-trip flights

Southwest Logo
6:00 pm - 7:00 pmRDU-MDW
2h 00mnonstop
Southwest Logo
10:00 am - 12:55 pmMDW-RDU
1h 55mnonstop
$139Southwest
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Tue, Sep 16 - Tue, Sep 23
Frontier Logo
6:10 am - 4:00 pmIAD-MDW
10h 50m1 stop
Frontier Logo
5:20 pm - 12:15 amMDW-IAD
5h 55m1 stop
$142Frontier
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Fri, Oct 3 - Mon, Oct 6
Frontier Logo
1:55 pm - 11:20 pmIAD-MDW
10h 25m1 stop
Frontier Logo
5:15 pm - 12:15 amMDW-IAD
6h 00m1 stop
$143Frontier
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Fri, Sep 5 - Mon, Sep 8
Frontier Logo
6:38 pm - 11:20 pmRDU-MDW
5h 42m1 stop
Frontier Logo
8:15 am - 1:38 pmMDW-RDU
4h 23m1 stop
$143Frontier
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Thu, Sep 4 - Mon, Sep 8
Frontier Logo
6:10 am - 4:00 pmIAD-MDW
10h 50m1 stop
Frontier Logo
6:20 am - 12:55 pmMDW-IAD
5h 35m1 stop
$144Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
4:14 pm - 8:21 pmORF-MDW
5h 07m1 stop
Frontier Logo
6:20 am - 2:54 pmMDW-ORF
7h 34m1 stop
$144Frontier
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Thu, Oct 23 - Sun, Oct 26
Frontier Logo
8:49 am - 5:27 pmRDU-MDW
9h 38m1 stop
Frontier Logo
8:25 am - 1:41 pmMDW-RDU
4h 16m1 stop
$144Frontier
Find Deal
Mon, Oct 20 - Thu, Oct 23
Southwest Logo
6:40 am - 7:35 amRDU-MDW
1h 55mnonstop
Southwest Logo
9:45 am - 12:35 pmMDW-RDU
1h 50mnonstop
$158Southwest
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Wed, Oct 1 - Fri, Oct 3
Delta Logo
5:45 am - 8:40 amRDU-MDW
3h 55m1 stop
Delta Logo
6:23 pm - 10:58 pmMDW-RDU
3h 35m1 stop
$197Delta
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Sat, Oct 4 - Mon, Oct 6
Delta Logo
5:45 am - 8:40 amRDU-MDW
3h 55m1 stop
Delta Logo
6:00 am - 11:13 amMDW-RDU
4h 13m1 stop
$207Delta
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Thu, Sep 11 - Tue, Sep 16

Southwest flights from Virginia to Chicago Midway Airport

Our best Southwest deals on Virginia to Chicago Midway Airport flight tickets
Southwest
Sep 16
RDU6:00 pmRaleigh-Durham
2h 00m
MDW7:00 pmChicago Midway
Sep 23
MDW10:00 amChicago Midway
1h 55m
RDU12:55 pmRaleigh-Durham
$139
Find similar
Southwest
Oct 1
RDU6:40 amRaleigh-Durham
1h 55m
MDW7:35 amChicago Midway
Oct 3
MDW9:45 amChicago Midway
1h 50m
RDU12:35 pmRaleigh-Durham
$158
Find similar
Southwest
Oct 2
RDU12:05 pmRaleigh-Durham
2h 00m
MDW1:05 pmChicago Midway
Oct 5
MDW8:20 pmChicago Midway
1h 50m
RDU11:10 pmRaleigh-Durham
$177
Find similar

Frontier flights from Virginia to Chicago Midway Airport

Our best Frontier deals on Virginia to Chicago Midway Airport flight tickets
Frontier
Oct 3
IAD6:10 amWashington, D.C. Dulles Intl
10h 50m
1 stop
MDW4:00 pmChicago Midway
Oct 6
MDW5:20 pmChicago Midway
5h 55m
1 stop
IAD12:15 amWashington, D.C. Dulles Intl
$142
Find similar
Frontier
Sep 4
RDU6:38 pmRaleigh-Durham
5h 42m
1 stop
MDW11:20 pmChicago Midway
Sep 8
MDW8:15 amChicago Midway
4h 23m
1 stop
RDU1:38 pmRaleigh-Durham
$143
Find similar
Frontier
Oct 23
ORF4:14 pmNorfolk
5h 07m
1 stop
MDW8:21 pmChicago Midway
Oct 26
MDW6:20 amChicago Midway
7h 34m
1 stop
ORF2:54 pmNorfolk
$144
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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 August 18, 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

Tue 9/16

6:00 pm-7:00 pm

Nonstop2h 00m

Chicago Midway

Tue 9/23

10:00 am-12:55 pm

Nonstop1h 55m

$139

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 10/3

6:10 am-4:00 pm

1 stop10h 50m

Chicago Midway

Mon 10/6

5:20 pm-12:15 am

1 stop5h 55m

$142

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/5

1:55 pm-11:20 pm

1 stop10h 25m

Chicago Midway

Mon 9/8

5:15 pm-12:15 am

1 stop6h 00m

$143

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 9/4

6:38 pm-11:20 pm

1 stop5h 42m

Chicago Midway

Mon 9/8

8:15 am-1:38 pm

1 stop4h 23m

$143

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Fri 9/5

6:10 am-4:00 pm

1 stop10h 50m

Chicago Midway

Mon 9/8

6:20 am-12:55 pm

1 stop5h 35m

$144

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 10/23

4:14 pm-8:21 pm

1 stop5h 07m

Chicago Midway

Sun 10/26

6:20 am-2:54 pm

1 stop7h 34m

$144

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 10/20

8:49 am-5:27 pm

1 stop9h 38m

Chicago Midway

Thu 10/23

8:25 am-1:41 pm

1 stop4h 16m

$144

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 10/1

6:40 am-7:35 am

Nonstop1h 55m

Chicago Midway

Fri 10/3

9:45 am-12:35 pm

Nonstop1h 50m

$158

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Sat 10/4

5:45 am-8:40 am

1 stop3h 55m

Chicago Midway

Mon 10/6

6:23 pm-10:58 pm

1 stop3h 35m

$197

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Thu 9/11

5:45 am-8:40 am

1 stop3h 55m

Chicago Midway

Tue 9/16

6:00 am-11:13 am

1 stop4h 13m

$207

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 $328. 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 $435. 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 $518.

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 $396 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 are 1 cabin classes 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?

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

$70

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Virginia in the past 72 hours is $70. The best round-trip flight deal from Virginia to Chicago Midway Airport found on momondo in the last 72 hours is $139.
The fastest flight from Virginia to Chicago Midway Airport takes 1h 55m
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
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $231Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
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Portage
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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