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Cheap flights from Norfolk to Chicago from $95

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Norfolk to Chicago departing on 8/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Norfolk to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:45 pm - 10:20 pm
ORF
-
MDW
7h 35m
2 stops
Southwest Logo
8:10 am - 5:55 pm
MDW
-
ORF
8h 45m
2 stops
$326Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
3:45 pm - 9:00 pm
ORF
-
MDW
6h 15m
1 stop
Southwest Logo
7:45 am - 10:55 am
MDW
-
ORF
2h 10mnonstop
$327Southwest
Thu, Aug 6 - Sat, Aug 8
Southwest Logo
6:45 pm - 7:50 pm
ORF
-
MDW
2h 05mnonstop
Southwest Logo
6:55 pm - 10:00 pm
MDW
-
ORF
2h 05mnonstop
$330Southwest
Fri, Aug 28 - Sun, Aug 30
Southwest Logo
7:15 pm - 8:20 pm
ORF
-
MDW
2h 05mnonstop
Southwest Logo
8:45 am - 12:00 pm
MDW
-
ORF
2h 15mnonstop
$333Southwest
Fri, Jul 31 - Tue, Aug 4
Delta Logo
6:00 am - 9:07 am
ORF
-
MDW
4h 07m
1 stop
Delta Logo
6:05 am - 2:09 pm
MDW
-
ORF
7h 04m
1 stop
$334Delta
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
12:10 pm - 7:15 pm
ORF
-
MDW
8h 05m
2 stops
Southwest Logo
10:00 am - 5:05 pm
MDW
-
ORF
6h 05m
2 stops
$335Southwest
Thu, Oct 8 - Sun, Oct 11
Delta Logo
6:14 pm - 10:36 pm
ORF
-
MDW
5h 22m
1 stop
Delta Logo
6:11 am - 12:45 pm
MDW
-
ORF
5h 34m
1 stop
$339Delta
Thu, Aug 13 - Sat, Aug 15
Southwest Logo
6:45 pm - 7:50 pm
ORF
-
MDW
2h 05mnonstop
Southwest Logo
8:50 am - 2:30 pm
MDW
-
ORF
4h 40m
1 stop
$340Southwest
Fri, Aug 28 - Sun, Aug 30
Frontier Logo
12:10 pm - 10:03 pm
ORF
-
MDW
10h 53m
1 stop
Frontier Logo
6:05 am - 11:15 am
MDW
-
ORF
28h 10m
1 stop
$342Frontier
Thu, Jul 30 - Sun, Aug 2
Southwest Logo
6:10 pm - 10:00 pm
ORF
-
MDW
4h 50m
1 stop
Southwest Logo
8:45 am - 12:00 pm
MDW
-
ORF
2h 15mnonstop
$343Southwest
Fri, Jul 31 - Tue, Aug 4

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Frontier flights from Norfolk to Chicago Midway Airport

Our best Frontier deals on Norfolk to Chicago Midway Airport flight tickets
Frontier
Jul 30
ORF12:10 pmNorfolk
10h 53m
1 stop
MDW10:03 pmChicago Midway
Aug 2
MDW6:05 amChicago Midway
28h 10m
1 stop
ORF11:15 amNorfolk
$342
Frontier
Jul 25
ORF12:16 pmNorfolk
10h 47m
1 stop
MDW10:03 pmChicago Midway
Jul 28
MDW12:11 pmChicago Midway
22h 04m
1 stop
ORF11:15 amNorfolk
$349
Frontier
Jul 29
ORF12:10 pmNorfolk
10h 53m
1 stop
MDW10:03 pmChicago Midway
Aug 3
MDW6:05 amChicago Midway
28h 10m
1 stop
ORF11:15 amNorfolk
$354

Southwest flights from Norfolk to Chicago Midway Airport

Our best Southwest deals on Norfolk to Chicago Midway Airport flight tickets
Southwest
Aug 13
ORF3:45 pmNorfolk
7h 35m
2 stops
MDW10:20 pmChicago Midway
Aug 17
MDW8:10 amChicago Midway
8h 45m
2 stops
ORF5:55 pmNorfolk
$326
Southwest
Aug 6
ORF3:45 pmNorfolk
6h 15m
1 stop
MDW9:00 pmChicago Midway
Aug 8
MDW7:45 amChicago Midway
2h 10m
ORF10:55 amNorfolk
$327
Southwest
Aug 28
ORF6:45 pmNorfolk
2h 05m
MDW7:50 pmChicago Midway
Aug 30
MDW6:55 pmChicago Midway
2h 05m
ORF10:00 pmNorfolk
$330

momondo Fare Finder

 
Customize your flight search to find flights from Norfolk to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated July 11, 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

Thu 8/13

3:45 pm-10:20 pm

2 stops7h 35m

Chicago Midway

Mon 8/17

8:10 am-5:55 pm

2 stops8h 45m

$326

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 8/6

3:45 pm-9:00 pm

1 stop6h 15m

Chicago Midway

Sat 8/8

7:45 am-10:55 am

Nonstop2h 10m

$327
Quickest round-trip

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 8/28

6:45 pm-7:50 pm

Nonstop2h 05m

Chicago Midway

Sun 8/30

6:55 pm-10:00 pm

Nonstop2h 05m

$330

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 7/31

7:15 pm-8:20 pm

Nonstop2h 05m

Chicago Midway

Tue 8/4

8:45 am-12:00 pm

Nonstop2h 15m

$333

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 9/11

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Tue 9/15

6:05 am-2:09 pm

1 stop7h 04m

$334

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 10/8

12:10 pm-7:15 pm

2 stops8h 05m

Chicago Midway

Sun 10/11

10:00 am-5:05 pm

2 stops6h 05m

$335

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 8/13

6:14 pm-10:36 pm

1 stop5h 22m

Chicago Midway

Sat 8/15

6:11 am-12:45 pm

1 stop5h 34m

$339

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 8/28

6:45 pm-7:50 pm

Nonstop2h 05m

Chicago Midway

Sun 8/30

8:50 am-2:30 pm

1 stop4h 40m

$340

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 7/30

12:10 pm-10:03 pm

1 stop10h 53m

Chicago Midway

Sun 8/2

6:05 am-11:15 am

1 stop28h 10m

$342

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 7/31

6:10 pm-10:00 pm

1 stop4h 50m

Chicago Midway

Tue 8/4

8:45 am-12:00 pm

Nonstop2h 15m

$343

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Norfolk to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Norfolk and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Norfolk, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Norfolk during the month September is also very affordable. Most momondo users find prices during this month for around $261.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Norfolk. The lowest ticket price found for a Tuesday departure recently was $440. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Norfolk because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $507.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Norfolk in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $416 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $519. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Norfolk to Chicago Midway flight route?

Fly from Norfolk to Chicago Midway for the best Norfolk - Chicago Midway flight prices

What cabin class options are available on Norfolk to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Norfolk to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Norfolk to Chicago Midway Airport flights?

You could potentially save up to 25% on your flight if you consider stops on a Norfolk to Chicago Midway Airport flight.

How have Norfolk to Chicago Midway Airport flight prices changed over time?

When to book flights from Norfolk to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Norfolk to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Norfolk to Chicago Midway Airport (ORF to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Norfolk to Chicago Midway Airport

Best Price Found

$233

Fastest flight time

2h 05m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Norfolk in the past 72 hours is $233. The best round-trip flight deal from Norfolk to Chicago Midway Airport found on momondo in the last 72 hours is $389.
The fastest flight from Norfolk to Chicago Midway Airport takes 2h 05m
Direct flights go from Norfolk to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Norfolk to Chicago Midway Airport

  • How far is Norfolk to Chicago Midway by plane?

    A flight from Norfolk to Chicago Midway will travel around 699.6 mi. Flights usually cover this in 2h 05m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Norfolk Airport to Chicago Midway Airport?

    Prices for flights from Norfolk Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Norfolk Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Norfolk Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Norfolk Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Norfolk to Chicago Midway Airport?

  • What is the most popular airline from Norfolk to Chicago Midway Airport?

Best airlines flying from Norfolk to Chicago Midway Airport

Compare and see reviews for airlines that fly from Norfolk to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $154Free CancellationRating
5.6
2,831 reviews
Search Frontier flights
SouthwestPriceFrom $231Free CancellationRating
7.9
4,248 reviews
Search Southwest flights

  • Southwest Flights From Norfolk to Chicago Midway Airport

    Across 12 Southwest flights from Norfolk to Chicago Midway Airport this week, the average price was $385, with the best Southwest deals starting from $231 round-trip. 4,250 users have rated Southwest on momondo, with an average score of 7.9/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Munster
Chesterton
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Crown Point
Porter
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Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Norfolk to Chicago?

It is quick and easy to find Norfolk to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Norfolk to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Norfolk which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Norfolk to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Norfolk.

I’m not ready to book a flight from Norfolk to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Norfolk to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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