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Cheap flights from Norfolk to Chicago from $73

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 10/6. 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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Find the cheapest flights from Norfolk to Chicago

Cheap round-trip flights

Frontier Logo
4:14 pm - 8:21 pmORF-MDW
5h 07m1 stop
Frontier Logo
6:20 am - 2:54 pmMDW-ORF
7h 34m1 stop
$144Frontier
Find Deal
Thu, Oct 23 - Sun, Oct 26
Frontier Logo
4:14 pm - 8:21 pmORF-MDW
5h 07m1 stop
Frontier Logo
6:20 am - 2:54 pmMDW-ORF
7h 34m1 stop
$160Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
12:19 pm - 11:20 pmORF-MDW
12h 01m1 stop
Frontier Logo
10:13 am - 4:57 pmMDW-ORF
5h 44m1 stop
$166Frontier
Find Deal
Fri, Sep 12 - Sun, Sep 14
Frontier Logo
12:14 pm - 11:20 pmORF-MDW
12h 06m1 stop
Frontier Logo
7:15 am - 5:50 pmMDW-ORF
9h 35m1 stop
$168Frontier
Find Deal
Sun, Sep 7 - Fri, Sep 12
Logo
5:38 pm - 9:51 amORF-MDW
17h 13m1 stop
Logo
8:19 am - 4:43 pmMDW-ORF
7h 24m1 stop
$209
Find Deal
Fri, Sep 12 - Mon, Sep 15
Logo
5:38 pm - 9:51 amORF-MDW
17h 13m1 stop
Logo
8:19 am - 4:39 pmMDW-ORF
7h 20m1 stop
$213
Find Deal
Fri, Oct 3 - Mon, Oct 6
Southwest Logo
5:35 am - 6:45 amORF-MDW
2h 10mnonstop
Southwest Logo
1:25 pm - 4:25 pmMDW-ORF
2h 00mnonstop
$237Southwest
Find Deal
Tue, Oct 7 - Tue, Oct 14
Southwest Logo
4:30 pm - 10:40 pmORF-MDW
7h 10m1 stop
Southwest Logo
1:25 pm - 4:25 pmMDW-ORF
2h 00mnonstop
$247Southwest
Find Deal
Tue, Oct 7 - Tue, Oct 14
Delta Logo
3:30 pm - 9:26 pmORF-MDW
6h 56m1 stop
Delta Logo
6:00 am - 12:49 pmMDW-ORF
5h 49m1 stop
$257Delta
Find Deal
Tue, Sep 9 - Wed, Sep 17
Delta Logo
3:30 pm - 9:26 pmORF-MDW
6h 56m1 stop
Delta Logo
6:15 pm - 11:11 pmMDW-ORF
3h 56m1 stop
$271Delta
Find Deal
Tue, Sep 9 - Mon, Sep 15

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 26
MDW6:20 amChicago Midway
7h 34m
1 stop
ORF2:54 pmNorfolk
$144
Find similar
Frontier
Oct 16
ORF4:14 pmNorfolk
5h 07m
1 stop
MDW8:21 pmChicago Midway
Oct 19
MDW6:20 amChicago Midway
7h 34m
1 stop
ORF2:54 pmNorfolk
$160
Find similar
Frontier
Sep 12
ORF12:19 pmNorfolk
12h 01m
1 stop
MDW11:20 pmChicago Midway
Sep 14
MDW10:13 amChicago Midway
5h 44m
1 stop
ORF4:57 pmNorfolk
$166
Find similar

Southwest flights from Norfolk to Chicago Midway Airport

Our best Southwest deals on Norfolk to Chicago Midway Airport flight tickets
Southwest
Oct 7
ORF5:35 amNorfolk
2h 10m
MDW6:45 amChicago Midway
Oct 14
MDW1:25 pmChicago Midway
2h 00m
ORF4:25 pmNorfolk
$237
Find similar
Southwest
Oct 7
ORF4:30 pmNorfolk
7h 10m
1 stop
MDW10:40 pmChicago Midway
Oct 14
MDW1:25 pmChicago Midway
2h 00m
ORF4:25 pmNorfolk
$247
Find similar
Southwest
Oct 13
ORF7:10 pmNorfolk
2h 10m
MDW8:20 pmChicago Midway
Oct 15
MDW6:05 pmChicago Midway
2h 00m
ORF9:05 pmNorfolk
$251
Find similar

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 August 18, 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 10/23

4:14 pm-8:21 pm

1 stop5h 07m

Chicago Midway

Sun 10/26

6:20 am-2:54 pm

1 stop7h 34m

$144

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Thu 10/16

4:14 pm-8:21 pm

1 stop5h 07m

Chicago Midway

Sun 10/19

6:20 am-2:54 pm

1 stop7h 34m

$160

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 9/12

12:19 pm-11:20 pm

1 stop12h 01m

Chicago Midway

Sun 9/14

10:13 am-4:57 pm

1 stop5h 44m

$166

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Sun 9/7

12:14 pm-11:20 pm

1 stop12h 06m

Chicago Midway

Fri 9/12

7:15 am-5:50 pm

1 stop9h 35m

$168

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 9/12

5:38 pm-9:51 am

1 stop17h 13m

Chicago Midway

Mon 9/15

8:19 am-4:43 pm

1 stop7h 24m

$209

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Fri 10/3

5:38 pm-9:51 am

1 stop17h 13m

Chicago Midway

Mon 10/6

8:19 am-4:39 pm

1 stop7h 20m

$213

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 10/7

5:35 am-6:45 am

Nonstop2h 10m

Chicago Midway

Tue 10/14

1:25 pm-4:25 pm

Nonstop2h 00m

$237

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 10/7

4:30 pm-10:40 pm

1 stop7h 10m

Chicago Midway

Tue 10/14

1:25 pm-4:25 pm

Nonstop2h 00m

$247

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 9/9

3:30 pm-9:26 pm

1 stop6h 56m

Chicago Midway

Wed 9/17

6:00 am-12:49 pm

1 stop5h 49m

$257

NorfolkChicago

ORF - MDW

ORFMDW

Norfolk

Tue 9/9

3:30 pm-9:26 pm

1 stop6h 56m

Chicago Midway

Mon 9/15

6:15 pm-11:11 pm

1 stop3h 56m

$271

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 $328. 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 $435. 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 $518.

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 $396 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $486. 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 are 1 cabin classes 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?

No. A direct flight is the cheapest option for a flight between Norfolk to Chicago Midway Airport.

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

$73

Fastest flight time

2h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Norfolk in the past 72 hours is $73. The best round-trip flight deal from Norfolk to Chicago Midway Airport found on momondo in the last 72 hours is $144.
The fastest flight from Norfolk to Chicago Midway Airport takes 2h 00m
Direct flights go from Norfolk to Chicago Midway Airport every day.
Search flight deals

  • 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 00m, 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 $231Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Norfolk to Chicago Midway Airport

    Across 9 Southwest flights from Norfolk to Chicago Midway Airport this week, the average price was $388, with the best Southwest deals starting from $231 round-trip. 4,246 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
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Hammond
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Portage
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Valparaiso
Crown Point
Munster
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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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