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$99+ Cheap flights from Norfolk (ORF) to Chicago (CHI)

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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORF — CHI
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Cheapflights Tip: The best prices from Norfolk to Chicago are usually found in September or December, booked 2 days in advance, depart on a Thursday or Wednesday and return on a Saturday

Cheap flight deals from Norfolk to Chicago

Cheapest flights from Norfolk to Chicago
Explore the most affordable flight options available from Norfolk to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2026.

This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:16 pm
ORF
-
MDW
1 stop10h 47m
Frontier
Wed 8/196:05 am
MDW
-
ORF
1 stop5h 20m
Frontier
Deal found 7/28$312
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/31:20 pm
ORF
-
ORD
1 stop19h 33m
Frontier
Sun 9/68:30 pm
ORD
-
ORF
2 stops14h 55m
Frontier
Deal found 7/27$312
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 10/87:30 am
ORF
-
ORD
2 stops13h 58m
Multiple Airlines
Sun 10/119:33 pm
ORD
-
ORF
1 stop13h 29m
Multiple Airlines
Deal found 7/27$313
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/217:00 am
ORF
-
MDW
2 stops17h 44m
Multiple Airlines
Thu 9/246:25 am
MDW
-
ORF
1 stop5h 04m
Multiple Airlines
Deal found 7/30$316
This Justfly.com deal was found by Cheapflights users on 7/31. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORF
-
ORD
1 stop8h 39m
JetBlue
Mon 8/2411:01 am
ORD
-
ORF
1 stop5h 09m
JetBlue
Deal found 7/31$316
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:45 pm
ORF
-
MDW
Nonstop2h 05m
Southwest
Mon 8/246:50 pm
MDW
-
ORF
Nonstop2h 05m
Southwest
Deal found 7/29$317
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:05 am
ORF
-
ORD
Nonstop2h 29m
United Airlines
Mon 9/1411:30 am
ORD
-
ORF
Nonstop2h 22m
United Airlines
Deal found 7/29$317
This Frontier deal was found by Cheapflights users on 8/1. 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.
Fri 9/41:20 pm
ORF
-
MDW
1 stop10h 27m
Frontier
Mon 9/76:05 am
MDW
-
ORF
1 stop5h 20m
Frontier
Deal found 8/1$318
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:24 am
ORF
-
ORD
Nonstop2h 36m
American Airlines
Mon 8/247:21 pm
ORD
-
ORF
Nonstop2h 21m
American Airlines
Deal found 7/30$318
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Sun 11/112:57 pm
ORF
-
MDW
1 stop9h 56m
Multiple Airlines
Mon 11/27:25 am
MDW
-
ORF
2 stops14h 18m
Multiple Airlines
Deal found 7/31$321
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Thu 8/201:20 pm
ORF
-
ORD
1 stop7h 39m
Frontier
Sat 8/222:41 pm
ORD
-
ORF
2 stops20h 44m
Frontier
Deal found 7/28$321
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:05 am
ORF
-
MDW
Nonstop2h 00m
Southwest
Fri 9/116:50 pm
MDW
-
ORF
Nonstop2h 10m
Southwest
Deal found 7/27$322

Find flight deals from Norfolk to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Norfolk (ORF) to Chicago (CHI). 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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$312
(Trip.com)

One-way from

$99
(Trip.com)

Popular in

July

Cheapest in

September

Average price

$367

Good round-trip deal

$378 or less

Good one-way deal

$233 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 Norfolk to Chicago (CHI)
Search Deals
One-way flight from Norfolk to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($44 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 August 2026
Search Deals
Price to beat on a round-trip flight from Norfolk to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Norfolk to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Norfolk to Chicago 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 August 1, 2026.
Use the filters below to find and compare flights from Norfolk to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 8/20

6:45 pm-7:50 pm

Nonstop2h 05m

Chicago Midway

Mon 8/24

6:50 pm-9:55 pm

Nonstop2h 05m

$317

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 9/11

6:45 pm-7:50 pm

Nonstop2h 05m

Chicago Midway

Tue 9/15

6:25 pm-9:35 pm

Nonstop2h 10m

$322

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Wed 9/16

6:05 am-7:34 am

Nonstop2h 29m

Chicago O'Hare Intl

Thu 9/17

4:00 pm-11:43 pm

1 stop6h 43m

$327

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 9/11

10:41 am-4:29 pm

1 stop6h 48m

Chicago O'Hare Intl

Tue 9/15

6:59 am-10:29 am

Nonstop2h 30m

$332

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Wed 9/16

10:05 am-7:35 pm

2 stops10h 30m

Chicago Midway

Thu 9/17

6:50 pm-10:00 pm

Nonstop2h 10m

$332

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 10/22

7:00 pm-8:10 pm

Nonstop2h 10m

Chicago Midway

Fri 10/23

6:45 pm-9:45 pm

Nonstop2h 00m

$338

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 9/24

1:05 pm-4:15 pm

1 stop4h 10m

Chicago Midway

Mon 9/28

2:35 pm-9:40 pm

2 stops6h 05m

$342

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Sat 8/29

11:30 am-1:04 pm

Nonstop2h 34m

Chicago O'Hare Intl

Tue 9/1

6:15 pm-9:48 pm

Nonstop2h 33m

$345

NorfolkChicago

ORF - ORD

ORFORD

Norfolk

Fri 9/4

10:41 am-4:52 pm

1 stop7h 11m

Chicago O'Hare Intl

Mon 9/7

7:30 am-11:00 am

Nonstop2h 30m

$348

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 9/25

10:10 am-2:05 pm

1 stop4h 55m

Chicago Midway

Tue 9/29

6:25 pm-9:35 pm

Nonstop2h 10m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 48 resultsSorted by cheapest first
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5

Compare providers for flights from Norfolk to Chicago

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 Chicago in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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 flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Norfolk-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Norfolk-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Norfolk-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, October is the cheapest month in which you can book a flight from Norfolk to Chicago (average of $317). Flying from Norfolk to Chicago in March is currently the most expensive (average of $439). 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 CHI?

Find hourly flight availability from Norfolk to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 1, 2026.

It’s typically best to fly out from Norfolk to Chicago in the afternoon. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Norfolk to Chicago

Explore weekly flight availability from Norfolk to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 1, 2026.

The most flights from ORF to CHI are scheduled on a Friday (25 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (11 on average).

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

Airfare is below average for this route at the moment.
Norfolk to Chicago flights typically cost between $327 and $460 in August.
The cheapest round-trip price found within the last 5 days was $312 on Frontier (Aug 15-Aug 19).

How far ahead should I book a flight from Norfolk to Chicago?

The price you pay for your flight from Norfolk to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 59 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Norfolk to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Norfolk to Chicago. Price data was last updated on August 1, 2026.

Travelers seeking maximum savings on their Norfolk to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 1, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Norfolk to Chicago 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
4,229 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,062 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,740 reviews
Southwest
8.0
Very good
4,229 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Norfolk to Chicago. 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?

    For a flight from Norfolk to Chicago, you will be flying from Norfolk. Norfolk (ORF) is just 5.9 mi from the center of the city. Norfolk is the only Norfolk airport and it handles 17 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Norfolk on a regular basis.

  • How long is the flight from Norfolk to Chicago?

    Departing from Norfolk to Chicago will take you 2h 05m. The distance between Norfolk and Chicago is about 702 mi. All flights are typically nonstop.

  • What are the cheapest airlines flying from Norfolk to Chicago round-trip?

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $72. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $217 and $243, respectively. Frontier is currently priced 80% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Norfolk to Chicago one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Norfolk to Chicago for a low price.

  • What are the most popular routes from Norfolk to Chicago?

    Most travelers choose Norfolk - Chicago O'Hare Intl, Norfolk - Chicago Midway or Norfolk - Chicago Greater Rockford when deciding on the best route from Norfolk to Chicago.

  • What are the most reliable airlines from Norfolk to Chicago?

    Consider ANA (84%), SkyWest Airlines (80%) or Envoy Air (78%) when booking your flight. These represent the most reliable airlines when flying from Norfolk to Chicago.

  • What are the cheapest flights from Norfolk to Chicago?

    On average you can expect to pay $1,190 for a flight from Norfolk to Chicago. The cheapest flight overall is $158 while the most popular route, (Norfolk - Chicago O'Hare Intl) is currently priced at $204.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Norfolk to Chicago 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?

    Currently, October is the cheapest month in which you can book a flight from Norfolk to Chicago (average of $317). Flying from Norfolk to Chicago in March is currently the most expensive (average of $439). 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?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 4 airlines flying from Norfolk to Chicago

Discover the top 4 airlines that operate flights from Norfolk to Chicago. 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$369FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$243Average$433FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$290Average$386FlexibilityNo cancel feeOn-time63%

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