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Midway

$64+ Cheap flights from Virginia to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MDW
jan 22 — jan 291
qui 1/22
qui 1/29
1 adult, Economy
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Cheap flight deals from Virginia to Midway

Cheapest flights from Virginia to Midway
Explore the most affordable flight options available from Virginia to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on dezembro 23, 2025.

This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 12/311:05 pmRDU - MDW
1 stop10h 07mFrontier
seg 1/56:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/22$162
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 12/306:14 pmRDU - MDW
1 stop21h 23mFrontier
seg 1/124:31 pmMDW - RDU
1 stop20h 27mFrontier
Deal found 12/22$180
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/2512:55 pmRDU - MDW
1 stop5h 43mFrontier
qui 1/812:41 pmMDW - RDU
1 stop10h 31mFrontier
Deal found 12/22$213
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 12/311:05 pmRDU - MDW
1 stop10h 07mFrontier
sex 1/26:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/22$217
This Expedia deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 12/291:15 pmRDU - MDW
1 stop9h 57mFrontier
seg 1/126:10 amMDW - RDU
1 stop9h 53mFrontier
Deal found 12/22$232
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 12/316:05 amIAD - MDW
1 stop8h 16mFrontier
qui 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/21$238
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 12/316:05 amIAD - MDW
1 stop8h 16mFrontier
seg 1/58:15 amMDW - IAD
1 stop9h 01mFrontier
Deal found 12/21$264
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/2512:55 pmRDU - MDW
1 stop5h 43mFrontier
qui 1/16:12 amMDW - RDU
1 stop4h 48mFrontier
Deal found 12/21$265
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/2512:55 pmRDU - MDW
1 stop10h 17mFrontier
sex 1/26:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/21$269
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 12/305:37 pmIAD - MDW
1 stop5h 35mFrontier
qui 1/16:12 amMDW - IAD
1 stop11h 04mFrontier
Deal found 12/21$282
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 12/261:15 pmRDU - MDW
1 stop9h 57mFrontier
seg 1/56:12 amMDW - RDU
1 stop5h 08mFrontier
Deal found 12/22$282
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 12/291:15 pmRDU - MDW
1 stop9h 57mFrontier
qua 12/316:12 amMDW - RDU
1 stop4h 48mFrontier
Deal found 12/22$283

Find flight deals from Virginia to Midway

Keep the following information in mind while searching for Virginia to Midway flight deals. Data was last updated dezembro 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$129
(CheapOair)

One-way from

$64
(Priceline)

Popular in

December

Cheapest in

September

Average price

$390

Good round-trip deal

$384 or less

Good one-way deal

$163 or less
Provider with most accurate pricing for Norfolk-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago (CHI) flights.
Search Deals
From Virginia to Chicago Midway
Search Deals
One-way flight from Virginia to Chicago Midway
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Virginia to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Virginia to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated dezembro 23, 2025.
Use the filters below to find and compare flights from Virginia to Chicago Midway Airport that are best for you.

Fly from

Virginia

Fly to

Midway

Route

Depart

Return

Price

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

qua 12/31

1:05 pm-10:12 pm

1 stop10h 07m

Chicago Midway

seg 1/5

6:12 am-12:20 pm

1 stop5h 08m

$162

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

sáb 1/17

6:15 am-7:25 am

Nonstop2h 10m

Chicago Midway

dom 1/18

1:25 pm-4:15 pm

Nonstop1h 50m

$163

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

qui 2/5

6:10 am-11:45 am

1 stop6h 35m

Chicago Midway

qui 2/12

6:25 am-6:00 pm

1 stop10h 35m

$164

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

dom 2/1

5:37 pm-10:19 pm

1 stop5h 42m

Chicago Midway

qui 2/5

6:20 am-4:28 pm

1 stop9h 08m

$174

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

seg 1/19

8:51 am-10:19 pm

1 stop14h 28m

Chicago Midway

seg 1/26

6:20 am-4:28 pm

1 stop9h 08m

$175

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

qui 2/19

5:37 pm-10:37 pm

1 stop6h 00m

Chicago Midway

dom 2/22

9:04 pm-10:40 am

1 stop12h 36m

$176

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

sex 2/6

9:35 am-7:52 pm

1 stop11h 17m

Chicago Midway

dom 2/8

6:20 am-4:33 pm

1 stop9h 13m

$179

RaleighChicago

RDU - MDW

RDUMDW

Raleigh-Durham

sex 2/27

6:10 am-6:38 pm

1 stop13h 28m

Chicago Midway

dom 3/1

9:04 pm-4:15 pm

1 stop18h 11m

$182

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

qui 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

dom 1/11

9:15 am-8:56 pm

1 stop10h 41m

$197

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

qui 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

sex 1/9

6:10 am-4:46 pm

1 stop9h 36m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Best time to book a flight from Virginia to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Virginia with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Virginia to Chicago Midway Airport

What is the cheapest month to book a flight from Virginia to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Virginia to Chicago Midway Airport (average of $175). Flying from Virginia to Chicago Midway Airport in January is currently the most expensive (average of $353). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from VA to MDW?

Find hourly flight availability from Virginia to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated dezembro 23, 2025.

It’s optimal to fly from Virginia to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Virginia to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Midway. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Virginia to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Virginia to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Virginia to Chicago Midway Airport?

    Departing from Virginia to Chicago Midway Airport will take you 2h 10m. Virginia and Chicago Midway Airport are separated by a distance of 631 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Virginia to Chicago Midway Airport?

    The most popular route from Virginia to Chicago Midway Airport is Washington, D.C. Dulles Intl - Chicago Midway. You may also consider Washington, D.C. Reagan-National - Chicago Midway or Raleigh-Durham - Chicago Midway.

  • What are the cheapest flights from Virginia to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $120. While the most popular route (Washington, D.C. Dulles Intl - Chicago Midway) can be booked for $146 on average, our data indicates $367 when flying from Virginia to Chicago Midway Airport.

  • Can I find deals for flights from Virginia to Midway that include hotel bookings?

    Yes. In addition to deals on Virginia to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia to Midway.

  • Can I find deals for business class flights from Virginia to Midway?

    Yes. Cheapflights offers flight deals from Virginia to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Virginia to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Virginia to Chicago Midway Airport (average of $175). Flying from Virginia to Chicago Midway Airport in January is currently the most expensive (average of $353). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Virginia to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Virginia to Midway

Discover the top 2 airlines that operate flights from Virginia to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated dezembro 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$181Average$364FlexibilityNo cancel feeOn-time63%
DeltaCheapest$228Average$351FlexibilityNo cancel feeOn-timeN/A

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