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Cheap flights from Virginia to Chicago from $100

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Virginia to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:16 pm - 12:01 amORF  Norfolk-MDW Chicago Midway
5h 45m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:35 pm - 4:19 pmMDW  Chicago Midway-ORF Norfolk
18h 44m1 stop Orlando
$305Frontier
Mon, Dec 21 - Tue, Dec 22
Frontier Logo
7:26 pm - 4:06 pmORF  Norfolk-MDW Chicago Midway
21h 40m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:02 pm - 6:31 pmMDW  Chicago Midway-ORF Norfolk
24h 29m1 stop Atlanta Hartsfield-Jackson
$305Frontier
Wed, Dec 9 - Fri, Dec 11
Frontier Logo
7:26 pm - 4:06 pmORF  Norfolk-MDW Chicago Midway
21h 40m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
5:02 pm - 4:14 pmMDW  Chicago Midway-ORF Norfolk
22h 12m2 stops Atlanta Hartsfield-Jackson Orlando
$306Frontier
Wed, Dec 9 - Sun, Dec 13
Southwest Logo
3:15 pm - 8:15 pmORF  Norfolk-MDW Chicago Midway
6h 00m1 stop Baltimore/Washington
Southwest Logo
7:10 pm - 10:20 pmMDW  Chicago Midway-ORF Norfolk
2h 10mnonstop
$307Southwest
Fri, Jan 15 - Mon, Jan 18
Southwest Logo
8:00 am - 9:15 amORF  Norfolk-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
4:25 pm - 9:15 pmMDW  Chicago Midway-ORF Norfolk
3h 50m1 stop Baltimore/Washington
$307Southwest
Thu, Dec 3 - Sat, Dec 5
Frontier Logo
7:16 pm - 12:01 amORF  Norfolk-MDW Chicago Midway
5h 45m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:30 pm - 5:27 pmMDW  Chicago Midway-ORF Norfolk
19h 57m1 stop Orlando
$307Frontier
Sat, Dec 26 - Sun, Jan 10
Southwest Logo
12:15 pm - 8:25 pmRIC  Richmond Byrd Intl-MDW Chicago Midway
9h 10m2 stops Nashville Intl Atlanta Hartsfield-Jackson
Southwest Logo
1:15 pm - 4:00 pmMDW  Chicago Midway-RIC Richmond Byrd Intl
1h 45mnonstop
$312Southwest
Tue, Dec 8 - Thu, Dec 10
Southwest Logo
6:10 am - 3:15 pmRIC  Richmond Byrd Intl-MDW Chicago Midway
10h 05m2 stops Baltimore/Washington Tampa
Southwest Logo
1:15 pm - 4:00 pmMDW  Chicago Midway-RIC Richmond Byrd Intl
1h 45mnonstop
$312Southwest
Sat, Dec 5 - Wed, Dec 9
Southwest Logo
6:15 am - 2:55 pmRIC  Richmond Byrd Intl-MDW Chicago Midway
9h 40m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson
Southwest Logo
7:40 am - 10:40 amMDW  Chicago Midway-RIC Richmond Byrd Intl
2h 00mnonstop
$312Southwest
Wed, Jan 6 - Sat, Jan 9
Southwest Logo
7:05 am - 8:10 amRIC  Richmond Byrd Intl-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
11:10 am - 7:50 pmMDW  Chicago Midway-RIC Richmond Byrd Intl
7h 40m2 stops Lambert-St Louis Nashville Intl
$312Southwest
Tue, Dec 15 - Thu, Dec 17

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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
Dec 3
ORF8:00 amNorfolk
2h 15m
MDW9:15 amChicago Midway
Dec 10
MDW8:50 amChicago Midway
3h 40m
1 stop
ORF1:30 pmNorfolk
$303
Southwest
Dec 3
ORF8:00 amNorfolk
2h 15m
MDW9:15 amChicago Midway
Dec 5
MDW4:25 pmChicago Midway
3h 50m
1 stop
ORF9:15 pmNorfolk
$307
Southwest
Jan 15
ORF3:15 pmNorfolk
6h 00m
2 stops
MDW8:15 pmChicago Midway
Jan 18
MDW7:10 pmChicago Midway
2h 10m
ORF10:20 pmNorfolk
$312

Frontier flights from Virginia to Chicago Midway Airport

Our best Frontier deals on Virginia to Chicago Midway Airport flight tickets
Frontier
Dec 9
ORF7:26 pmNorfolk
21h 40m
1 stop
MDW4:06 pmChicago Midway
Dec 11
MDW5:02 pmChicago Midway
24h 29m
1 stop
ORF6:31 pmNorfolk
$305
Frontier
Dec 9
ORF7:26 pmNorfolk
21h 40m
1 stop
MDW4:06 pmChicago Midway
Dec 13
MDW5:02 pmChicago Midway
22h 12m
2 stops
ORF4:14 pmNorfolk
$306
Frontier
Dec 2
ORF7:24 pmNorfolk
21h 43m
1 stop
MDW4:07 pmChicago Midway
Dec 9
MDW12:28 pmChicago Midway
5h 03m
1 stop
ORF6:31 pmNorfolk
$316

momondo Fare Finder

 
Use the filters below to find and compare flights from Virginia to Chicago Midway Airport that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Mon 12/21

7:16 pm-12:01 am

1 stop5h 45m

Chicago Midway

Tue 12/22

8:35 pm-4:19 pm

1 stop18h 44m

$305

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Wed 12/9

7:26 pm-4:06 pm

1 stop21h 40m

Chicago Midway

Fri 12/11

5:02 pm-6:31 pm

1 stop24h 29m

$305

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Wed 12/9

7:26 pm-4:06 pm

1 stop21h 40m

Chicago Midway

Sun 12/13

5:02 pm-4:14 pm

2 stops22h 12m

$306

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Fri 1/15

3:15 pm-8:15 pm

1 stop6h 00m

Chicago Midway

Mon 1/18

7:10 pm-10:20 pm

Nonstop2h 10m

$307
Quickest round-trip

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Thu 12/3

8:00 am-9:15 am

Nonstop2h 15m

Chicago Midway

Sat 12/5

4:25 pm-9:15 pm

1 stop3h 50m

$307

NorfolkChicago

ORF Norfolk - MDW Chicago Midway

ORFMDW

Norfolk

Sat 12/26

7:16 pm-12:01 am

1 stop5h 45m

Chicago Midway

Sun 1/10

8:30 pm-5:27 pm

1 stop19h 57m

$307

RichmondChicago

RIC Richmond Byrd Intl - MDW Chicago Midway

RICMDW

Richmond Byrd Intl

Tue 12/8

12:15 pm-8:25 pm

2 stops9h 10m

Chicago Midway

Thu 12/10

1:15 pm-4:00 pm

Nonstop1h 45m

$312

RichmondChicago

RIC Richmond Byrd Intl - MDW Chicago Midway

RICMDW

Richmond Byrd Intl

Sat 12/5

6:10 am-3:15 pm

2 stops10h 05m

Chicago Midway

Wed 12/9

1:15 pm-4:00 pm

Nonstop1h 45m

$312

RichmondChicago

RIC Richmond Byrd Intl - MDW Chicago Midway

RICMDW

Richmond Byrd Intl

Wed 1/6

6:15 am-2:55 pm

2 stops9h 40m

Chicago Midway

Sat 1/9

7:40 am-10:40 am

Nonstop2h 00m

$312

RichmondChicago

RIC Richmond Byrd Intl - MDW Chicago Midway

RICMDW

Richmond Byrd Intl

Tue 12/15

7:05 am-8:10 am

Nonstop2h 05m

Chicago Midway

Thu 12/17

11:10 am-7:50 pm

2 stops7h 40m

$312

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 March is, on average, the cheapest month to fly to Chicago Midway Airport from Virginia, with most prices found around $347. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Virginia during the month January is also very affordable. Most momondo users find prices during this month for around $350.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Virginia. The lowest ticket price found for a Friday departure recently was $464. 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 $514.

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 $443 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $526. 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 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?

You could potentially save up to 31% 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

$100

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 $100. The best round-trip flight deal from Virginia to Chicago Midway Airport found on momondo in the last 72 hours is $305.
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

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
SouthwestPriceFrom $290Free CancellationRating
8.0
4,214 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
Lansing
Benton Harbor
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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