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Cheap flights from Virginia to Chicago from $78

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 9/10. 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
1 adult, Economy, 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.
Southwest Logo
11:50 am - 12:45 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
11:15 am - 2:05 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$184Southwest
Sun, Sep 6 - Sat, Sep 12
Southwest Logo
4:35 pm - 5:35 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
12:00 pm - 2:50 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$184Southwest
Tue, Sep 1 - Thu, Sep 10
Southwest Logo
9:35 am - 10:30 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
11:05 am - 1:55 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 50mnonstop
$184Southwest
Wed, Sep 2 - Sun, Sep 6
Frontier Logo
7:50 am - 5:46 pmIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
10h 56m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 5:18 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
9h 53m1 stop Atlanta Hartsfield-Jackson
$186Frontier
Tue, Sep 22 - Sat, Oct 3
Frontier Logo
6:20 am - 10:55 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
5h 35m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:05 am - 5:14 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
10h 09m1 stop Atlanta Hartsfield-Jackson
$187Frontier
Wed, Sep 2 - Fri, Sep 4
Frontier Logo
7:00 am - 10:58 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 58m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:03 pm - 12:28 amMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
11h 25m1 stop Atlanta Hartsfield-Jackson
$192Frontier
Tue, Nov 10 - Wed, Nov 11
Delta Logo
6:10 am - 9:07 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
3h 57m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:03 pm - 11:14 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
5h 11m1 stop Detroit Metropolitan Wayne County
$197Delta
Fri, Sep 11 - Fri, Sep 11
Delta Logo
6:10 am - 9:17 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 4:30 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
6h 01m1 stop Detroit Metropolitan Wayne County
$197Delta
Sun, Sep 6 - Fri, Sep 11
Multiple Airlines Logo
9:01 pm - 10:58 amRDU  Raleigh-Durham-MDW Chicago Midway
14h 57m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:03 pm - 12:17 amMDW  Chicago Midway-RDU Raleigh-Durham
11h 14m1 stop Atlanta Hartsfield-Jackson
$239Multiple Airlines
Fri, Oct 30 - Mon, Nov 9
Multiple Airlines Logo
7:00 am - 10:58 amIAD  Washington, D.C. Dulles Intl-MDW Chicago Midway
4h 58m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:26 pm - 8:21 pmMDW  Chicago Midway-IAD Washington, D.C. Dulles Intl
29h 55m2 stops Knoxville McGhee Tyson Fort Lauderdale
$286Multiple Airlines
Fri, Oct 23 - Mon, Oct 26

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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
Sep 6
DCA11:50 amWashington, D.C. Reagan-National
1h 55m
MDW12:45 pmChicago Midway
Sep 12
MDW11:15 amChicago Midway
1h 50m
DCA2:05 pmWashington, D.C. Reagan-National
$184
Southwest
Sep 11
DCA9:15 pmWashington, D.C. Reagan-National
2h 00m
MDW10:15 pmChicago Midway
Sep 15
MDW8:40 amChicago Midway
6h 10m
2 stops
DCA3:50 pmWashington, D.C. Reagan-National
$185
Southwest
Sep 10
DCA12:15 pmWashington, D.C. Reagan-National
4h 15m
1 stop
MDW3:30 pmChicago Midway
Sep 10
MDW9:00 pmChicago Midway
1h 55m
DCA11:55 pmWashington, D.C. Reagan-National
$187

Frontier flights from Virginia to Chicago Midway Airport

Our best Frontier deals on Virginia to Chicago Midway Airport flight tickets
Frontier
Sep 22
IAD7:50 amWashington, D.C. Dulles Intl
10h 56m
1 stop
MDW5:46 pmChicago Midway
Oct 3
MDW6:25 amChicago Midway
9h 53m
1 stop
IAD5:18 pmWashington, D.C. Dulles Intl
$186
Frontier
Sep 2
IAD6:20 amWashington, D.C. Dulles Intl
5h 35m
1 stop
MDW10:55 amChicago Midway
Sep 4
MDW6:05 amChicago Midway
10h 09m
1 stop
IAD5:14 pmWashington, D.C. Dulles Intl
$187
Frontier
Sep 1
IAD11:05 amWashington, D.C. Dulles Intl
12h 42m
2 stops
MDW10:47 pmChicago Midway
Sep 5
MDW6:05 amChicago Midway
10h 09m
1 stop
IAD5:14 pmWashington, D.C. Dulles Intl
$192

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 13, 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
Quickest round-trip

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Sun 9/6

11:50 am-12:45 pm

Nonstop1h 55m

Chicago Midway

Sat 9/12

11:15 am-2:05 pm

Nonstop1h 50m

$184

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Tue 9/1

4:35 pm-5:35 pm

Nonstop2h 00m

Chicago Midway

Thu 9/10

12:00 pm-2:50 pm

Nonstop1h 50m

$184

Washington, D.C.Chicago

DCA Washington, D.C. Reagan-National - MDW Chicago Midway

DCAMDW

Washington, D.C. Reagan-National

Wed 9/2

9:35 am-10:30 am

Nonstop1h 55m

Chicago Midway

Sun 9/6

11:05 am-1:55 pm

Nonstop1h 50m

$184

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 9/22

7:50 am-5:46 pm

1 stop10h 56m

Chicago Midway

Sat 10/3

6:25 am-5:18 pm

1 stop9h 53m

$186

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Wed 9/2

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Fri 9/4

6:05 am-5:14 pm

1 stop10h 09m

$187

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Tue 11/10

7:00 am-10:58 am

1 stop4h 58m

Chicago Midway

Wed 11/11

12:03 pm-12:28 am

1 stop11h 25m

$192

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Fri 9/11

6:10 am-9:07 am

1 stop3h 57m

Chicago Midway

Fri 9/11

5:03 pm-11:14 pm

1 stop5h 11m

$197

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Sun 9/6

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Fri 9/11

9:29 am-4:30 pm

1 stop6h 01m

$197

RaleighChicago

RDU Raleigh-Durham - MDW Chicago Midway

RDUMDW

Raleigh-Durham

Fri 10/30

9:01 pm-10:58 am

2 stops14h 57m

Chicago Midway

Mon 11/9

12:03 pm-12:17 am

1 stop11h 14m

$239

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - MDW Chicago Midway

IADMDW

Washington, D.C. Dulles Intl

Fri 10/23

7:00 am-10:58 am

1 stop4h 58m

Chicago Midway

Mon 10/26

1:26 pm-8:21 pm

2 stops29h 55m

$286

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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Virginia, with most prices found around $286. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Virginia during the month October is also very affordable. Most momondo users find prices during this month for around $330.

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 $440. 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 $522.

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 $422 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $519. 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

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

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

$233

Fastest flight time

1h 50m

Direct flights

Mon, Tue, Wed, Thu, Fri and Sat
The best one-way flight to Chicago Midway Airport from Virginia in the past 72 hours is $233. The best round-trip flight deal from Virginia to Chicago Midway Airport found on momondo in the last 72 hours is $370.
The fastest flight from Virginia to Chicago Midway Airport takes 1h 50m
Direct flights go from Virginia to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday, Friday and Saturday. There are no airlines offering direct flights.
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
2,695 reviews
Search Frontier flights
SouthwestPriceFrom $178Free CancellationRating
8.0
4,218 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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