$748 Cheap Flights from Auckland (AKL) to Chicago (MDW)

View $748 flight on Sat, Feb 7, 2026Opens in a new window

Popular airlines from Auckland Intl. Airport (AKL) to Chicago Midway Airport (MDW)

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Find available prices by choosing your travel dates.

Cheap Flights from Auckland to Chicago (AKL-MDW)

Prices were available within the past 7 days and start at $748 for one-way flights and $2,332 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Dec 20 - Sat, Jan 3
AKL
Auckland
MDW
Chicago
$2,332 Roundtrip, found 5 days ago
$2,332
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Dec 20 from Auckland to Chicago, returning Sat, Jan 3, priced at $2,332 found 5 days ago
Flights from Auckland (AKL) to Chicago (MDW)
Origin airport
Auckland Intl.
Destination airport
Midway Intl.
Roundtrip price
$2,332
Distance
8193 mi

Auckland to Chicago Flights

The cheapest times to fly from Auckland 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 Auckland to Chicago are during the month of December. You can find some of the cheapest flights from Auckland to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Auckland to Chicago

Sunday is one of the best days to book for cheap flights from Auckland 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 Auckland 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 Auckland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $748 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 Auckland 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 Auckland 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 Auckland Intl. Airport (AKL) to Midway Intl. Airport (MDW) last minute?
When it’s time to book your flights, being prepared pays off. While you may be able to score a last-minute deal on an Auckland Airport to MDW flight, fares usually don’t get cheaper as the departure date nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days ahead. For international flights it’s between three and four months.
What airports do you fly into for Chicago from Auckland?
With Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to choose from, connecting from Auckland to Chicago is easy. The city’s key hub, Midway Intl. Airport (MDW), is roughly 9 mi southwest of the downtown area. As well as the price of fares, consider things like public transportation options from the airport and the distance to your hotel when deciding where to touch down. Get your Chicago trip off to a flying start by discovering Wrigley Field and Millennium Park.
Can I change the date of my flight from AKL to Chicago Airport?
You can easily make changes to your AKL to MDW flight through the Expedia Trips portal. But before you make any adjustments, look over the conditions and rules in your itinerary to learn what the carrier will let you do and if charges apply. Some carriers have a change fee per person, plus any difference in fare prices. But if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also take a look at our Customer Service portal for further details and to connect with our Virtual Agent.

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