Route guide · 827 miles
Cheap Flights from Chicago to New Orleans
MDW → MSY · Nonstop 2h 11m · Live round-trip fares
The run from Chicago (MDW) to New Orleans (MSY) is 827 miles of sky, and ticket prices on it are anything but steady. One week can cost double the next. Booking about 3–6 weeks in advance — and watching fares with a free Airfare Deal alert — is how regulars on this route keep costs down.
Live fares for MDW → MSY are updating. Use the search below for real-time prices.
Search live pricesCheapest recent fare
See live fares
Updated daily
Flight time
2h 11m
Nonstop, typical
Distance
827 mi
MDW → MSY
Book ahead
3–6 weeks
Best window, typically
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Chicago to New Orleans
The fastest way between the two cities is the nonstop: about 2h 11m for the 827-mile run from MDW to MSY. Those flights are flown by Southwest Airlines. Prices behave best when you book 3–6 weeks out.
Booking insights: Chicago → New Orleans
- Distance: 827 miles · nonstop flight time: 2h 11m.
- Fares tend to bottom out when you book about 3–6 weeks ahead — earlier than that rarely helps, later usually hurts.
- Midweek departures (Tue–Thu) are consistently cheaper than weekend flights.
- A free fare alert beats daily checking: we watch this route and ping you when prices drop.
Free fare alerts
Watch Chicago (MDW) → New Orleans (MSY)
We check this route's fares daily. The moment the price drops, we'll email you — free, unsubscribe anytime.
Talk to a real person
Get Chicago → New Orleans flights confirmed by phone
Fares move fast. Call us and we'll confirm the latest price for your dates — or drop your number and we'll call you back. Free, no payment taken on the call.
Request a callback
Flying from Chicago to New Orleans: what you need to know
The flight
The nonstop from MDW to MSY runs about 2h 11m over 827 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 Chicago (MDW)
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 Chicago airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in New Orleans (MSY)
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 New Orleans airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check New Orleans to Chicago fares — prices on the return direction often move on a different rhythm.
When to book
For a trip of 827 miles, booking 3–6 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
- 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.
- If you're traveling with only a carry-on, you can skip the bag-drop line entirely with mobile check-in.
Chicago to New Orleans flight FAQs
How long is the flight from MDW to MSY?
A nonstop from MDW to MSY clocks in at around 2h 11m for the 827-mile trip. If you're connecting, budget an extra 2–4 hours depending on where you stop.
Are there nonstop flights from Chicago to New Orleans?
Southwest Airlines typically operate nonstop flights from MDW to MSY. Nonstops are usually cheapest when booked 3–6 weeks ahead of departure.
What is the cheapest month to fly from Chicago to New Orleans?
There's no single magic month, but prices on this route generally soften in the shoulder season, when demand dips after the holidays and again in early fall. A free fare alert is the easiest way to catch those windows.
How much are last minute flights from MDW to MSY?
Last-minute flights from MDW to MSY (booked within 7 days of departure) typically cost noticeably more than fares booked 3–6 weeks out. Booking early is the smarter move.
What is a good round-trip deal from Chicago to New Orleans?
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 Chicago to New Orleans?
You'll mainly see Southwest Airlines on Chicago to New Orleans. 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 Chicago 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 Chicago
How Airfare Deal works — Airfare Deal is a free fare-search and enquiry service. We take no payment online; send an enquiry and our travel team confirms your fare before you pay anything.