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Midway

$70+ Cheap flights from Norfolk (ORF) 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORF — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Norfolk to Midway

Cheapest flights from Norfolk to Midway
Explore the most affordable flight options available from Norfolk to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This Priceline deal was found by Cheapflights users on 12/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:11 pmORF - MDW
1 stop7h 47mFrontier
Mon 1/56:12 amMDW - ORF
1 stop5h 57mFrontier
Deal found 12/11$264
This Frontier deal was found by Cheapflights users on 12/10. 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.
Wed 12/3111:44 amORF - MDW
1 stop11h 28mFrontier
Mon 1/56:12 amMDW - ORF
1 stop5h 57mFrontier
Deal found 12/10$283
This Priceline deal was found by Cheapflights users on 12/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:11 pmORF - MDW
1 stop7h 47mFrontier
Sat 1/38:15 amMDW - ORF
1 stop7h 12mFrontier
Deal found 12/10$307
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Tue 12/307:40 pmORF - MDW
2 stops27h 32mMultiple Airlines
Fri 1/26:12 amMDW - ORF
1 stop6h 27mMultiple Airlines
Deal found 12/9$331
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Tue 12/303:11 pmORF - MDW
2 stops32h 01mMultiple Airlines
Mon 1/53:10 pmMDW - ORF
1 stop26h 35mMultiple Airlines
Deal found 12/11$359
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/233:11 pmORF - MDW
1 stop7h 47mMultiple Airlines
Sun 1/410:50 pmMDW - ORF
2 stops42h 55mMultiple Airlines
Deal found 12/10$363
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Mon 12/227:40 pmORF - MDW
1 stop27h 18mMultiple Airlines
Sat 1/36:12 amMDW - ORF
1 stop9h 15mMultiple Airlines
Deal found 12/10$384
This Priceline deal was found by Cheapflights users on 12/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/192:34 pmORF - MDW
1 stop8h 38mFrontier
Mon 12/296:12 amMDW - ORF
1 stop5h 57mFrontier
Deal found 12/10$392
This Southwest deal was found by Cheapflights users on 12/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:05 amORF - MDW
1 stop6h 55mSouthwest
Mon 12/299:40 pmMDW - ORF
1 stop10h 50mSouthwest
Deal found 12/10$397

Find flight deals from Norfolk to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Norfolk (ORF) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$264
(Priceline)

One-way from

$70
(Expedia)

Popular in

March

Cheapest in

September

Average price

$359

Good round-trip deal

$370 or less

Good one-way deal

$254 or less
Provider with most accurate pricing for Norfolk-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Chicago Midway flights.
Search Deals
From Norfolk to Chicago Midway
Search Deals
One-way flight from Norfolk to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 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 Norfolk to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Norfolk to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Norfolk 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 December 12, 2025.
Use the filters below to find and compare flights from Norfolk to Chicago Midway Airport that are best for you.

Fly from

Norfolk

Fly to

Midway

Route

Depart

Return

Price

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 12/31

11:44 am-10:12 pm

1 stop11h 28m

Chicago Midway

Mon 1/5

6:12 am-1:09 pm

1 stop5h 57m

$283

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 1/14

6:30 am-11:35 am

1 stop6h 05m

Chicago Midway

Wed 1/14

5:30 pm-8:30 pm

Nonstop2h 00m

$302

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 1/6

5:35 pm-6:50 pm

Nonstop2h 15m

Chicago Midway

Wed 1/14

1:15 pm-5:50 pm

1 stop3h 35m

$302

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 1/17

6:14 pm-10:07 pm

1 stop4h 53m

Chicago Midway

Sun 1/18

5:59 pm-12:16 am

1 stop5h 17m

$317

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 1/7

6:30 am-1:55 pm

2 stops8h 25m

Chicago Midway

Fri 1/9

5:30 pm-8:30 pm

Nonstop2h 00m

$319

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 1/26

8:50 am-2:55 pm

1 stop7h 05m

Chicago Midway

Thu 1/29

5:30 pm-8:30 pm

Nonstop2h 00m

$333

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 3/11

10:50 am-4:53 pm

1 stop7h 03m

Chicago Midway

Sat 3/14

9:32 am-4:16 pm

1 stop5h 44m

$343

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 1/19

5:20 am-11:59 am

1 stop7h 39m

Chicago Midway

Thu 1/22

6:14 pm-12:16 am

1 stop5h 02m

$343

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 1/24

6:16 pm-10:22 pm

1 stop5h 06m

Chicago Midway

Sun 1/25

6:00 am-2:29 pm

1 stop7h 29m

$349

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 1/8

6:30 am-1:10 pm

2 stops7h 40m

Chicago Midway

Mon 1/12

1:15 pm-5:50 pm

1 stop3h 35m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 22 results
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2
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Compare providers for flights from Norfolk to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Norfolk to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Norfolk-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Norfolk-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Norfolk-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Norfolk-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Norfolk-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Norfolk to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Norfolk 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 Norfolk to Chicago Midway Airport

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

Currently, September is the cheapest month in which you can book a flight from Norfolk to Chicago Midway Airport (average of $175). Flying from Norfolk 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 ORF to MDW?

Find hourly flight availability from Norfolk 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 December 12, 2025.

When flying from Norfolk to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 21% versus a flight in the evening.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated December 12, 2025.
See what other customers who have flown with Southwest from Norfolk to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,253 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

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

  • What airport do you fly from for flights from Norfolk to Chicago Midway?

    Norfolk (ORF), located 5.9 mi from the city center, is the airport you fly out of when you book flights from Norfolk to Chicago Midway. 1 airline have flights from Norfolk to Chicago Midway on a regular basis. Booking flights from Norfolk to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

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

    Frontier, Southwest, and Delta can get you from Norfolk to Chicago Midway Airport in just under 4h 53m. Your travel time can differ by up to 6h 35m. There are 702 mi between Norfolk and Chicago Midway Airport. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Norfolk to Chicago Midway Airport round-trip?

    Southwest, at $261, was found to be the cheapest airline from Norfolk to Chicago Midway Airport.. You may be able to fly from Norfolk to Chicago Midway Airport for 30% less than the average price by searching for this airline.

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

    Looking for the cheapest flight from Norfolk to Chicago Midway Airport? While on average our users pay $370, our data indicates the cheapest price to be $137. The most popular route (Norfolk - Chicago Midway), is priced around $188.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Norfolk 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 Norfolk to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Norfolk to Chicago Midway Airport (average of $175). Flying from Norfolk 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 Norfolk to Midway

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Top airline flying from Norfolk to Midway

Discover the top airline that operate flights from Norfolk 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$261Average$379FlexibilityNo cancel feeOn-time63%

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