Route guide · 703 miles
Cheap Flights from Norfolk to Chicago
ORF → MDW · Nonstop 1h 56m · Live round-trip fares
If Chicago is next on your list, here's the honest picture on fares from Norfolk. The trip covers about 703 miles and takes roughly 1h 56m in the air. Prices on this route reward planners: booking 2–4 weeks ahead is the sweet spot, and the lowest fares tend to sell out fast.
Live fares for ORF → MDW are updating. Use the search below for real-time prices.
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See live fares
Updated daily
Flight time
1h 56m
Nonstop, typical
Distance
703 mi
ORF → MDW
Book ahead
2–4 weeks
Best window, typically
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Norfolk to Chicago
Nonstop flights from Norfolk to Chicago are flown by Southwest Airlines. The 703-mile trip takes about 1h 56m gate to gate, and nonstops are usually cheapest when booked 2–4 weeks ahead.
Booking insights: Norfolk → Chicago
- Distance: 703 miles · nonstop flight time: 1h 56m.
- Cheapest upcoming week in the live data starts around Oct 15, with fares from $148.
- Fares tend to bottom out when you book about 2–4 weeks ahead — earlier than that rarely helps, later usually hurts.
- Tuesday and Wednesday departures usually undercut Friday and Sunday fares on routes like this one.
- A free fare alert beats daily checking: we watch this route and ping you when prices drop.
Cheapest month · Norfolk → Chicago
October 2026
Every date's recent round-trip fare, at a glance.
Fares from
$148
Cheapest: Thu, Oct 15 — $148
Get this fare →Recent fares found for specific dates in October 2026. Blank days had no recent fare in our data — ask our team and we'll check them for you.
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Flying from Norfolk to Chicago: what you need to know
The flight
The nonstop from ORF to MDW runs about 1h 56m over 703 miles. It's a comfortable mid-range flight: long enough that seat choice matters a little, short enough that paying up for extras rarely does.
Airlines on this route
Southwest Airlines flies this route nonstop. That matters more than it sounds: the cheapest fare on one carrier is rarely the same product as the cheapest on another. Checked-bag fees, free seat selection and change rules all differ, so compare the full trip cost before you pick a winner. See our airline guides for exactly what each carrier charges — then send an enquiry and we'll confirm the all-in price for your dates.
Leaving from Norfolk (ORF)
Plan to be at the airport two hours before a domestic departure — ninety minutes can work at smaller airports outside peak times, but security lines are the one variable you can't control. If you're checking a bag, add time rather than cutting it close. Our Norfolk airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Chicago (MDW)
Before you land, know how you're getting from the airport to where you're staying — it's the part of the trip people forget to plan. The Chicago airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Chicago to Norfolk fares — prices on the return direction often move on a different rhythm.
When to book
For a trip of 703 miles, booking 2–4 weeks ahead typically lands you in the sweet spot. Leave it to the final two weeks and prices usually climb as the cheapest seats sell out. If your dates are flexible, midweek departures are where the lower fares hide on most domestic routes.
Good to know before you go
- Screenshot your fare before you enquire — prices move, and a saved fare helps our team match or beat it.
- Flexible dates? Search a few days either side — one day can change the fare a lot.
- Morning flights are delayed less often than evening ones — earlier departures have the best on-time record.
- Basic economy fares often exclude checked bags and seat selection. Price the whole trip, not the headline fare.
- Get to the airport two hours before departure; security, not the flight, is the part that runs late.
Norfolk to Chicago flight FAQs
How long is the flight from ORF to MDW?
Plan on about 1h 56m in the air for a nonstop from Norfolk to Chicago — the route runs roughly 703 miles. Connecting flights typically add 2–4 hours.
Are there nonstop flights from Norfolk to Chicago?
Southwest Airlines typically operate nonstop flights from ORF to MDW. Nonstops are usually cheapest when booked 2–4 weeks ahead of departure.
What is the cheapest month to fly from Norfolk to Chicago?
Fares from Norfolk to Chicago tend to ease outside the peak summer and holiday rush — the late-summer and early-fall shoulder weeks are usually kinder on the wallet. Set a free Airfare Deal alert and we'll flag the dips for your dates.
How much are last minute flights from ORF to MDW?
Book inside the final week and you'll usually pay a premium on ORF to MDW. Fares booked 2–4 weeks ahead are almost always kinder.
What is a good round-trip deal from Norfolk to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from Norfolk to Chicago?
You'll mainly see Southwest Airlines on Norfolk to Chicago. Checking each against the live fares below is the surest way to find the lowest price for your dates.
How early should I get to Norfolk airport for this flight?
Plan on two hours before departure for a domestic flight — ninety minutes can work at smaller airports outside peak times. If you're checking a bag, earlier is better; the bag-drop line, not the flight, is what runs late.
Do the cheapest fares on this route include a checked bag?
Usually not. Basic economy fares on most airlines include a carry-on but charge extra for checked bags, and seat selection can cost more too. Add up the real total before comparing — a slightly higher regular fare sometimes works out cheaper. Our team confirms the full breakdown with you before you pay.
More cheap flights from Norfolk
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