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$55+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORF — MDW
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(Kiwi.com)

One-way from

$55
(Priceline)

Popular in

March

Cheapest in

September

Average price

$354

Good round-trip deal

$416 or less

Good one-way deal

$273 or less
Provider with most accurate pricing for Norfolk-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Chicago Midway flights.
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From Norfolk to Chicago Midway
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One-way flight from Norfolk to Chicago Midway
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Norfolk to Chicago Midway.
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Price to beat on a one-way flight from Norfolk to Chicago Midway.
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Find 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/268:02 pmORF - MDW
2 stops27h 41mMultiple Airlines
Mon 12/15:47 pmMDW - ORF
1 stop25h 44mMultiple Airlines
Deal found 10/29$207
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 11/126:33 pmORF - MDW
1 stop15h 39mMultiple Airlines
Mon 11/176:06 pmMDW - ORF
1 stop20h 35mMultiple Airlines
Deal found 10/28$214
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 12/58:11 pmORF - MDW
2 stops18h 48mMultiple Airlines
Sun 12/76:37 pmMDW - ORF
1 stop12h 06mMultiple Airlines
Deal found 10/29$216
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 11/144:57 pmORF - MDW
1 stop18h 29mMultiple Airlines
Mon 11/171:37 pmMDW - ORF
2 stops27h 01mMultiple Airlines
Deal found 10/28$217
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/118:38 amORF - MDW
2 stops14h 34mMultiple Airlines
Mon 12/156:15 amMDW - ORF
1 stop9h 05mMultiple Airlines
Deal found 10/27$218
This Frontier deal was found by Cheapflights users on 10/27. 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.
Mon 11/1711:29 amORF - MDW
1 stop11h 42mFrontier
Fri 11/216:05 amMDW - ORF
1 stop8h 16mFrontier
Deal found 10/27$230

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 October 29, 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

Fri 11/14

7:00 am-4:57 pm

1 stop10h 57m

Chicago Midway

Sun 11/16

6:06 pm-10:18 pm

1 stop27h 12m

$250

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 12/6

8:11 pm-1:01 pm

2 stops17h 50m

Chicago Midway

Mon 12/8

6:15 am-4:20 pm

1 stop9h 05m

$274

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 12/12

5:30 am-6:40 am

Nonstop2h 10m

Chicago Midway

Wed 12/17

6:05 pm-9:05 pm

Nonstop2h 00m

$290

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 12/30

7:40 pm-9:58 pm

1 stop27h 18m

Chicago Midway

Sat 1/3

6:12 am-4:27 pm

1 stop9h 15m

$293

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 12/6

5:30 pm-6:40 pm

Nonstop2h 10m

Chicago Midway

Mon 12/8

6:05 pm-9:05 pm

Nonstop2h 00m

$294

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 3/3

9:40 am-4:25 pm

1 stop7h 45m

Chicago Midway

Wed 3/4

5:59 pm-11:29 pm

1 stop4h 30m

$295

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 11/26

9:26 pm-10:43 pm

2 stops26h 17m

Chicago Midway

Sun 11/30

5:30 pm-9:43 am

1 stop15h 13m

$300

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 1/27

5:35 pm-6:50 pm

Nonstop2h 15m

$133

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 2/18

5:35 pm-6:50 pm

Nonstop2h 15m

$138

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 2/4

5:35 pm-6:50 pm

Nonstop2h 15m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 18 results
1
2

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 October.
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 December is currently the most expensive (average of $366). 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 October 29, 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 20% 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 October 29, 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
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 1 outbound flight to Chicago Midway per day.

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

    Southwest can get you from Norfolk to Chicago Midway Airport in just under 2h 10m. Your travel time will be generally consistent. There are 702 mi between Norfolk and Chicago Midway Airport. Most flights are nonstop.

  • 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 $401, our data indicates the cheapest price to be $154. The most popular route (Norfolk - Chicago Midway), is priced around $139.

  • 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 December is currently the most expensive (average of $366). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Norfolk to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$261Average$390FlexibilityNo cancel feeOn-time63%

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