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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 4/25. 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
12:33 pm - 11:04 am
RDU
-
MDW
23h 31m
1 stop
Frontier Logo
6:00 am - 11:59 am
MDW
-
RDU
4h 59m
1 stop
$167Frontier
Fri, May 8 - Sun, May 10
Frontier Logo
3:42 pm - 10:19 pm
RDU
-
MDW
7h 37m
1 stop
Frontier Logo
8:21 am - 4:42 pm
MDW
-
RDU
7h 21m
1 stop
$168Frontier
Mon, Apr 27 - Thu, Apr 30
Frontier Logo
6:15 am - 11:09 am
RDU
-
MDW
5h 54m
1 stop
Frontier Logo
11:59 am - 12:29 am
MDW
-
RDU
11h 30m
1 stop
$169Frontier
Wed, May 6 - Sat, May 16
Frontier Logo
12:33 pm - 10:02 pm
RDU
-
MDW
10h 29m
1 stop
Frontier Logo
4:52 pm - 9:21 am
MDW
-
RDU
15h 29m
1 stop
$171Frontier
Wed, May 13 - Mon, May 18
Southwest Logo
10:55 am - 5:00 pm
DCA
-
MDW
7h 05m
1 stop
Southwest Logo
6:35 pm - 9:30 pm
MDW
-
DCA
1h 55mnonstop
$215Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
12:15 pm - 2:45 pm
DCA
-
MDW
3h 30m
1 stop
Southwest Logo
1:55 pm - 6:40 pm
MDW
-
DCA
3h 45m
1 stop
$216Southwest
Sat, May 9 - Tue, May 12
Delta Logo
6:00 am - 8:47 am
IAD
-
MDW
3h 47m
1 stop
Delta Logo
9:27 am - 4:15 pm
MDW
-
IAD
5h 48m
1 stop
$224Delta
Tue, Apr 14 - Thu, Apr 16
Delta Logo
6:05 am - 8:43 am
DCA
-
MDW
3h 38m
1 stop
Delta Logo
1:22 pm - 6:59 pm
MDW
-
DCA
4h 37m
1 stop
$224Delta
Sat, May 9 - Tue, May 12
Multiple Airlines Logo
12:20 pm - 7:31 pm
RIC
-
MDW
8h 11m
1 stop
Multiple Airlines Logo
6:00 am - 7:50 pm
MDW
-
RIC
12h 50m
2 stops
$304Multiple Airlines
Thu, Apr 23 - Thu, Apr 30
Multiple Airlines Logo
12:20 pm - 7:31 pm
RIC
-
MDW
8h 11m
1 stop
Multiple Airlines Logo
2:00 pm - 7:50 pm
MDW
-
RIC
28h 50m
2 stops
$305Multiple Airlines
Thu, Apr 23 - Sun, Apr 26

Frontier flights from Virginia to Chicago Midway Airport

Our best Frontier deals on Virginia to Chicago Midway Airport flight tickets
Frontier
May 8
RDU12:33 pmRaleigh-Durham
23h 31m
1 stop
MDW11:04 amChicago Midway
May 10
MDW6:00 amChicago Midway
4h 59m
1 stop
RDU11:59 amRaleigh-Durham
$167
Frontier
Apr 27
RDU3:42 pmRaleigh-Durham
7h 37m
1 stop
MDW10:19 pmChicago Midway
Apr 30
MDW8:21 amChicago Midway
7h 21m
1 stop
RDU4:42 pmRaleigh-Durham
$168
Frontier
May 6
RDU6:15 amRaleigh-Durham
5h 54m
1 stop
MDW11:09 amChicago Midway
May 16
MDW11:59 amChicago Midway
11h 30m
1 stop
RDU12:29 amRaleigh-Durham
$169

Southwest flights from Virginia to Chicago Midway Airport

Our best Southwest deals on Virginia to Chicago Midway Airport flight tickets
Southwest
Apr 22
RDU6:40 pmRaleigh-Durham
2h 00m
MDW7:40 pmChicago Midway
Apr 29
MDW7:25 amChicago Midway
6h 30m
1 stop
RDU2:55 pmRaleigh-Durham
$211
Southwest
Apr 22
RDU5:00 pmRaleigh-Durham
7h 05m
1 stop
MDW11:05 pmChicago Midway
Apr 29
MDW7:40 amChicago Midway
1h 50m
RDU10:30 amRaleigh-Durham
$213
Southwest
Apr 22
DCA3:40 pmWashington, D.C. Reagan-National
2h 10m
MDW4:50 pmChicago Midway
Apr 29
MDW1:55 pmChicago Midway
3h 45m
1 stop
DCA6:40 pmWashington, D.C. Reagan-National
$215

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 March 25, 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

Fri 5/8

12:33 pm-11:04 am

1 stop23h 31m

Chicago Midway

Sun 5/10

6:00 am-11:59 am

1 stop4h 59m

$167

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Mon 4/27

3:42 pm-10:19 pm

1 stop7h 37m

Chicago Midway

Thu 4/30

8:21 am-4:42 pm

1 stop7h 21m

$168

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 5/6

6:15 am-11:09 am

1 stop5h 54m

Chicago Midway

Sat 5/16

11:59 am-12:29 am

1 stop11h 30m

$169

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

Wed 5/13

12:33 pm-10:02 pm

1 stop10h 29m

Chicago Midway

Mon 5/18

4:52 pm-9:21 am

1 stop15h 29m

$171

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 5/5

10:55 am-5:00 pm

1 stop7h 05m

Chicago Midway

Sat 5/9

6:35 pm-9:30 pm

Nonstop1h 55m

$215
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/9

12:15 pm-2:45 pm

1 stop3h 30m

Chicago Midway

Tue 5/12

1:55 pm-6:40 pm

1 stop3h 45m

$216

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 4/14

6:00 am-8:47 am

1 stop3h 47m

Chicago Midway

Thu 4/16

9:27 am-4:15 pm

1 stop5h 48m

$224

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/9

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Tue 5/12

1:22 pm-6:59 pm

1 stop4h 37m

$224

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 4/23

12:20 pm-7:31 pm

1 stop8h 11m

Chicago Midway

Thu 4/30

6:00 am-7:50 pm

2 stops12h 50m

$304

RichmondChicago

RIC - MDW

RICMDW

Richmond Byrd Intl

Thu 4/23

12:20 pm-7:31 pm

1 stop8h 11m

Chicago Midway

Sun 4/26

2:00 pm-7:50 pm

2 stops28h 50m

$305

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 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 $414. 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 $479.

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 $388 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $469. 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.

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

$183

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 $183. The best round-trip flight deal from Virginia to Chicago Midway Airport found on momondo in the last 72 hours is $379.
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

  • 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
5.7
3,017 reviews
Search Frontier flights
SouthwestPriceFrom $178Free CancellationRating
8.0
4,333 reviews
Search Southwest flights
DeltaPriceFrom $228Free CancellationRating
7.9
8,326 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
Schererville
Munster
Crown Point
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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