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$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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORF — MDW
May 24 — May 311
Sun 5/24
Sun 5/31
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 April 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/148:34 pm
ORF
-
MDW
1 stop20h 23m
Multiple Airlines
Mon 5/186:00 am
MDW
-
ORF
2 stops10h 39m
Multiple Airlines
Deal found 4/20$281
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/2212:06 pm
ORF
-
MDW
1 stop10h 56m
Frontier
Mon 5/2512:04 pm
MDW
-
ORF
1 stop22h 07m
Frontier
Deal found 4/20$284
This Expedia deal was found by Cheapflights users on 4/19. 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.
Thu 4/2311:27 am
ORF
-
MDW
1 stop11h 52m
Frontier
Sat 4/259:14 am
MDW
-
ORF
1 stop8h 07m
Frontier
Deal found 4/19$285
This Southwest deal was found by Cheapflights users on 4/23. 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.
Tue 5/126:25 pm
ORF
-
MDW
Nonstop2h 10m
Southwest
Sat 5/167:50 am
MDW
-
ORF
Nonstop2h 00m
Southwest
Deal found 4/23$294
This Trip.com deal was found by Cheapflights users on 4/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:27 am
ORF
-
MDW
1 stop11h 52m
Frontier
Sat 5/29:14 am
MDW
-
ORF
1 stop8h 07m
Frontier
Deal found 4/19$296
This Southwest deal was found by Cheapflights users on 4/19. 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.
Tue 5/196:25 pm
ORF
-
MDW
Nonstop2h 10m
Southwest
Tue 5/266:05 pm
MDW
-
ORF
Nonstop2h 05m
Southwest
Deal found 4/19$297
This Southwest deal was found by Cheapflights users on 4/23. 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.
Tue 5/266:25 pm
ORF
-
MDW
Nonstop2h 10m
Southwest
Wed 5/276:05 pm
MDW
-
ORF
Nonstop2h 05m
Southwest
Deal found 4/23$298
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 6/512:06 pm
ORF
-
MDW
1 stop10h 56m
Frontier
Mon 6/86:00 am
MDW
-
ORF
2 stops13h 17m
Frontier
Deal found 4/19$299
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
ORF
-
MDW
1 stop3h 43m
Delta
Mon 6/85:11 pm
MDW
-
ORF
1 stop5h 27m
Delta
Deal found 4/21$301
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:06 pm
ORF
-
MDW
1 stop10h 56m
Multiple Airlines
Fri 5/84:52 pm
MDW
-
ORF
1 stop24h 57m
Multiple Airlines
Deal found 4/21$302
This Frontier deal was found by Cheapflights users on 4/21. 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.
Sat 4/2511:27 am
ORF
-
MDW
1 stop8h 10m
Frontier
Mon 4/279:14 am
MDW
-
ORF
1 stop9h 52m
Frontier
Deal found 4/21$305
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 7/2812:21 pm
ORF
-
MDW
1 stop10h 50m
Multiple Airlines
Fri 8/712:04 pm
MDW
-
ORF
2 stops9h 44m
Multiple Airlines
Deal found 4/19$306

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 April 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Kiwi.com)

One-way from

$70
(Trip.com)

Popular in

May

Cheapest in

September

Average price

$378

Good round-trip deal

$437 or less

Good one-way deal

$229 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 ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 24, 2026.
Use the filters below to find and compare flights from Norfolk to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 5/12

8:40 am-4:15 pm

1 stop8h 35m

Chicago Midway

Sat 5/16

7:50 am-10:50 am

Nonstop2h 00m

$309

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 5/19

12:45 pm-4:45 pm

1 stop5h 00m

Chicago Midway

Tue 5/26

11:35 am-9:55 pm

2 stops9h 20m

$322

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 6/4

6:00 am-8:43 am

1 stop3h 43m

Chicago Midway

Mon 6/8

5:11 pm-11:38 pm

1 stop5h 27m

$350

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 7/1

7:00 pm-8:10 pm

Nonstop2h 10m

Chicago Midway

Tue 7/7

12:00 pm-3:00 pm

Nonstop2h 00m

$363
Quickest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 7/8

7:50 am-8:50 am

Nonstop2h 00m

Chicago Midway

Mon 7/13

7:40 am-10:45 am

Nonstop2h 05m

$365

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 6/5

6:10 pm-10:00 pm

1 stop4h 50m

Chicago Midway

Sun 6/7

7:00 pm-10:00 pm

Nonstop2h 00m

$373

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 6/27

6:35 pm-7:40 pm

Nonstop2h 05m

Chicago Midway

Tue 6/30

5:30 pm-10:35 pm

1 stop4h 05m

$375

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 6/12

6:17 pm-10:17 pm

1 stop5h 00m

Chicago Midway

Tue 6/16

6:05 am-11:27 am

1 stop4h 22m

$385
Cheapest one-way

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 6/24

12:21 pm-10:11 pm

1 stop10h 50m

$88

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 7/19

12:21 pm-11:07 am

1 stop23h 46m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 19 resultsSorted by cheapest first
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Norfolk-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 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 April 24, 2026.

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 18% versus a flight in the evening.

How much does it cost to fly round-trip from Norfolk to Chicago Midway Airport?

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 April 24, 2026.
See what other customers who have flown with Southwest and Frontier 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
4,334 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,980 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. 2 airlines 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?

    Southwest and Delta can get you from Norfolk to Chicago Midway Airport in just under 3h 43m. Your travel time can differ by up to 4h 52m. 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 are the cheapest airlines flying from Norfolk to Chicago Midway Airport round-trip?

    Frontier, at $154, was found to be the cheapest airline from Norfolk to Chicago Midway Airport. An alternate airline flying to your destination would be Southwest. You may be able to fly from Norfolk to Chicago Midway Airport for 58% less than the average price by searching for these airlines.

  • 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 $378, our data indicates the cheapest price to be $201. The most popular route (Norfolk - Chicago Midway), is priced around $214.

  • 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 2 airlines flying from Norfolk to Midway

Discover the top 2 airlines 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 April 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$154Average$315FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$231Average$375FlexibilityNo cancel feeOn-time63%

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