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Cheap flights from Norfolk to Chicago from $80

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 11/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:20 pm - 10:03 pmORF-MDW
7h 43m1 stop
Multiple Airlines Logo
9:30 am - 10:58 pmMDW-ORF
12h 28m1 stop
$219Multiple Airlines
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Thu, Nov 13 - Thu, Nov 20
Multiple Airlines Logo
7:00 am - 4:57 pmORF-MDW
10h 57m1 stop
Multiple Airlines Logo
10:12 am - 12:24 pmMDW-ORF
25h 12m1 stop
$220Multiple Airlines
Find Deal
Fri, Nov 14 - Sun, Nov 16
Frontier Logo
11:41 am - 6:39 pmORF-MDW
7h 58m1 stop
Frontier Logo
6:06 pm - 10:47 amMDW-ORF
15h 41m2 stops
$244Frontier
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Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
5:38 pm - 11:25 pmORF-MDW
30h 47m2 stops
Multiple Airlines Logo
11:36 am - 1:16 pmMDW-ORF
24h 40m1 stop
$248Multiple Airlines
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Mon, Oct 27 - Sat, Nov 1
Multiple Airlines Logo
7:00 am - 2:22 pmORF-MDW
8h 22m1 stop
Multiple Airlines Logo
6:06 pm - 10:18 pmMDW-ORF
27h 12m1 stop
$262Multiple Airlines
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Fri, Oct 31 - Sun, Nov 2
Frontier Logo
11:42 am - 6:39 pmORF-MDW
7h 57m1 stop
Frontier Logo
1:56 pm - 12:21 pmMDW-ORF
45h 25m2 stops
$269Frontier
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Fri, Oct 31 - Tue, Nov 4
Southwest Logo
5:30 pm - 6:40 pmORF-MDW
2h 10mnonstop
Southwest Logo
6:05 pm - 9:05 pmMDW-ORF
2h 00mnonstop
$270Southwest
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Sat, Nov 8 - Tue, Nov 11
Delta Logo
5:40 am - 12:34 pmORF-MDW
7h 54m1 stop
Delta Logo
6:48 pm - 11:22 pmMDW-ORF
3h 34m1 stop
$276Delta
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Thu, Nov 20 - Mon, Nov 24
Southwest Logo
5:45 pm - 10:35 pmORF-MDW
5h 50m1 stop
Southwest Logo
8:50 am - 4:45 pmMDW-ORF
6h 55m1 stop
$285Southwest
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Sat, Nov 8 - Tue, Nov 11
Delta Logo
5:40 am - 12:34 pmORF-MDW
7h 54m1 stop
Delta Logo
9:34 am - 11:22 pmMDW-ORF
12h 48m1 stop
$286Delta
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Thu, Nov 20 - Mon, Nov 24

Frontier flights from Norfolk to Chicago Midway Airport

Our best Frontier deals on Norfolk to Chicago Midway Airport flight tickets
Frontier
Oct 23
ORF4:14 pmNorfolk
5h 07m
1 stop
MDW8:21 pmChicago Midway
Oct 25
MDW6:15 amChicago Midway
5h 12m
1 stop
ORF12:27 pmNorfolk
$218
Find similar
Frontier
Nov 6
ORF11:41 amNorfolk
7h 58m
1 stop
MDW6:39 pmChicago Midway
Nov 9
MDW6:06 pmChicago Midway
15h 41m
2 stops
ORF10:47 amNorfolk
$244
Find similar
Frontier
Oct 31
ORF11:42 amNorfolk
7h 57m
1 stop
MDW6:39 pmChicago Midway
Nov 4
MDW1:56 pmChicago Midway
45h 25m
2 stops
ORF12:21 pmNorfolk
$269
Find similar

Southwest flights from Norfolk to Chicago Midway Airport

Our best Southwest deals on Norfolk to Chicago Midway Airport flight tickets
Southwest
Nov 8
ORF5:30 pmNorfolk
2h 10m
MDW6:40 pmChicago Midway
Nov 11
MDW6:05 pmChicago Midway
2h 00m
ORF9:05 pmNorfolk
$270
Find similar
Southwest
Nov 8
ORF5:45 pmNorfolk
5h 50m
1 stop
MDW10:35 pmChicago Midway
Nov 11
MDW8:50 amChicago Midway
6h 55m
1 stop
ORF4:45 pmNorfolk
$285
Find similar
Southwest
Nov 20
ORF5:30 pmNorfolk
2h 10m
MDW6:40 pmChicago Midway
Nov 24
MDW5:05 amChicago Midway
7h 20m
1 stop
ORF1:25 pmNorfolk
$296
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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 October 16, 2025.
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

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/13

3:20 pm-10:03 pm

1 stop7h 43m

Chicago Midway

Thu 11/20

9:30 am-10:58 pm

1 stop12h 28m

$219

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 11/14

7:00 am-4:57 pm

1 stop10h 57m

Chicago Midway

Sun 11/16

10:12 am-12:24 pm

1 stop25h 12m

$220

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/6

11:41 am-6:39 pm

1 stop7h 58m

Chicago Midway

Sun 11/9

6:06 pm-10:47 am

2 stops15h 41m

$244

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Mon 10/27

5:38 pm-11:25 pm

2 stops30h 47m

Chicago Midway

Sat 11/1

11:36 am-1:16 pm

1 stop24h 40m

$248

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 10/31

7:00 am-2:22 pm

1 stop8h 22m

Chicago Midway

Sun 11/2

6:06 pm-10:18 pm

1 stop27h 12m

$262

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 10/31

11:42 am-6:39 pm

1 stop7h 57m

Chicago Midway

Tue 11/4

1:56 pm-12:21 pm

2 stops45h 25m

$269

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 11/8

5:30 pm-6:40 pm

Nonstop2h 10m

Chicago Midway

Tue 11/11

6:05 pm-9:05 pm

Nonstop2h 00m

$270

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/20

5:40 am-12:34 pm

1 stop7h 54m

Chicago Midway

Mon 11/24

6:48 pm-11:22 pm

1 stop3h 34m

$276

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sat 11/8

5:45 pm-10:35 pm

1 stop5h 50m

Chicago Midway

Tue 11/11

8:50 am-4:45 pm

1 stop6h 55m

$285

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 11/20

5:40 am-12:34 pm

1 stop7h 54m

Chicago Midway

Mon 11/24

9:34 am-11:22 pm

1 stop12h 48m

$286

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 cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Norfolk, with most prices found around $261. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Norfolk during the month April is also very affordable. Most momondo users find prices during this month for around $335.

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 $429. 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, Saturday 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 $521.

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 $391 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $492. 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 flights?

There is only 1 cabin class available to choose from on Norfolk to Chicago Midway 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 50% 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

$253

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Norfolk in the past 72 hours is $253. The best round-trip flight deal from Norfolk to Chicago Midway Airport found on momondo in the last 72 hours is $368.
The fastest flight from Norfolk to Chicago Midway Airport takes 2h 10m
Direct flights go from Norfolk to Chicago Midway Airport every day.
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  • 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 10m, 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
SouthwestPriceFrom $261Free CancellationRating
8.0
4,241 reviews
Search Southwest flights

  • Southwest Flights From Norfolk to Chicago Midway Airport

    Across 10 Southwest flights from Norfolk to Chicago Midway Airport this week, the average price was $388, with the best Southwest deals starting from $261 round-trip. 4,241 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
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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