$94 Cheap Flights from Norfolk (ORF) to Chicago (MDW)

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Find available prices by choosing your travel dates.

Cheap Flights from Norfolk to Chicago (ORF-MDW)

Prices were available within the past 7 days and start at $94 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Delta
Southwest Airlines
Flights from Norfolk (ORF) to Chicago (MDW)
Origin airport
Norfolk Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$188
Distance
701 mi

Norfolk to Chicago Flights

The cheapest times to fly from Norfolk to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Norfolk to Chicago are during the month of May. You can find some of the cheapest flights from Norfolk to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Norfolk to Chicago

Sunday is one of the best days to book for cheap flights from Norfolk to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Norfolk to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Norfolk to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $94 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Norfolk to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Norfolk to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

Is it cheaper to buy a plane ticket from Norfolk Intl. Airport (ORF) to Chicago Airport last minute?
Being the spontaneous type is a wonderful way to discover the world, but it isn’t necessarily the cleverest way to find a cheap fare. It’s better to book your Norfolk Intl. Airport to Midway Intl. Airport (MDW) trip in advance rather than leaving it until the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. Save up that spontaneity for when you get to your destination!
What airports do you fly into for Chicago from Norfolk?
With Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to select from, making your way from Norfolk to Chicago is a snap. The city’s busiest terminal, Midway Intl. Airport (MDW), is approximately 9 mi southwest of the center. Besides the price of fares, consider things like public transportation options from the airport and the distance to your hotel before making your choice. Get your Chicago trip off to a terrific start by checking out Wrigley Field and Millennium Park.
Can I change the date of my flight from ORF to Midway Airport?
We know plans can change, so Expedia is here to help make amending your flight as easy as possible. To start, find your Norfolk Intl. Airport (ORF) to Chicago Airport itinerary through the Expedia Trips portal and browse the ticket conditions and rules regarding changes. If you booked your ticket in the last 24 hours, some airlines will let you cancel for free and book new flights. If you bought your fare more than 24 hours ago, connect with us via our Customer Service portal to find out your options.

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*Available to One Key members.