$1,026 Find Cheap Flights to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 29/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Cheap Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent return flight deals to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
American Airlines Logo
15:50 - 06:06AKL-ORD
31h 16m2 stops
American Airlines Logo
07:35 - 10:25ORD-AKL
33h 50m2 stops
$1,887American Airlines
Find Deal
Thu, 29 May - Mon, 9 Jun
 Logo
14:30 - 17:27AKL-ORD
43h 57m3 stops
 Logo
07:56 - 12:40ORD-AKL
35h 44m3 stops
$1,912
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Qantas Airways Logo
06:20 - 21:08CHC-ORD
31h 48m2 stops
Qantas Airways Logo
17:51 - 14:45ORD-CHC
27h 54m2 stops
$2,062Qantas Airways
Find Deal
Thu, 5 Jun - Thu, 12 Jun
Air Canada Logo
19:45 - 06:19AKL-ORD
27h 34m1 stop
Air Canada Logo
15:35 - 14:55ORD-AKL
30h 20m2 stops
$2,064Air Canada
Find Deal
Sun, 1 Jun - Sun, 22 Jun
Qantas Airways Logo
06:00 - 15:55AKL-ORD
26h 55m2 stops
Qantas Airways Logo
18:53 - 14:05ORD-AKL
26h 12m2 stops
$2,065Qantas Airways
Find Deal
Wed, 4 Jun - Wed, 11 Jun
Air Canada Logo
19:45 - 11:32AKL-ORD
32h 47m1 stop
Air Canada Logo
15:35 - 14:55ORD-AKL
30h 20m2 stops
$2,087Air Canada
Find Deal
Fri, 6 Jun - Sun, 22 Jun
United Airlines Logo
19:40 - 14:48AKL-ORD
36h 08m1 stop
United Airlines Logo
14:35 - 05:00ORD-AKL
20h 25m1 stop
$2,194United Airlines
Find Deal
Fri, 26 Sep - Sun, 28 Sep
Air New Zealand Logo
13:50 - 14:49AKL-ORD
17h 59m1 stop
Air New Zealand Logo
14:33 - 06:00ORD-AKL
22h 27m1 stop
$2,406Air New Zealand
Find Deal
Mon, 12 May - Fri, 30 May
Air New Zealand Logo
19:40 - 08:01AKL-ORD
29h 21m1 stop
Air New Zealand Logo
19:40 - 06:00ORD-AKL
41h 20m1 stop
$2,424Air New Zealand
Find Deal
Thu, 29 May - Mon, 9 Jun
United Airlines Logo
19:40 - 21:30AKL-ORD
18h 50m1 stop
United Airlines Logo
21:40 - 05:30ORD-AKL
38h 50m1 stop
$2,477United Airlines
Find Deal
Mon, 2 Jun - Wed, 18 Jun

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends into flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $1,937. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $2,241 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago is February, where tickets cost $1,647 on average for return flights. On the other hand, the most expensive months are April and July, where the average cost of tickets from New Zealand is $2,456 and $2,329 respectively. For one-way flights, the best month to travel is February with an average price of $1,647.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $1,209 on average. The most expensive time of day to fly to Chicago is generally at night, which is peak travel time and where the average cost of a ticket is $1,304.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport (MDW), with an average flight price of $391.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

High season

June

Cheapest flight

$1,026
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly and prices are also 0% lower on average.
Flight from Auckland to Chicago

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    There are 3 airports in Chicago. The closest airport to Chicago’s city centre is Chicago Midway Airport (14 km). Chicago O'Hare Airport and Chicago Greater Rockford are respectively 26 km and 126 km from the centre of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $950. The cheapest price found on KAYAK in the last 2 weeks cost $890 and departed from Auckland Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

New Zealand to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to New Zealand

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Top 4 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from New Zealand to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Air New ZealandOverall score based on 469 reviews
7.3Food
8.0Comfort
8.5Crew
8.2Boarding
7.4Entertainment
Airline reviews

Again, Air New Zealand was great. They kept bathrooms clean, food was actually very good, New Zealand wines a big hit

10.0 ExcellentAnonymous, Apr 2025AKL - IAH
Read more Air New Zealand reviews

Again, Air New Zealand was great. They kept bathrooms clean, food was actually very good, New Zealand wines a big hit

The issue was with getting our boarding pases. There were issues with our arrangements that were made through Kayak. I am sorry to say that we will not use you again because of this. The flight itself was good and the flight attendants excellent.

Arriving at Coolangatta, rows 20 forward, took the airbridge across to the terminal. It was suggested to those from rows 21 back, that we take the rear stairs and to be careful crossing the tarmac. That was all well and good. However, when we got across to the terminal we then had to climb three large flights of stairs to meet up with those coming across the airbridge. No elevator! There were people carrying babies and elderly carrying hand luggage that needed assistance from others.. There was no option to turn back.

It was good for a short domestic flight. As no food ar entertainment provided, there should be a n/a rating available for those.

USB charging ports did not work on any of Air New Zealand flights

Economy was much nicer on the Air New Zealand planes.

At Coolangatta International it is difficult to hear voice boarding announcements when away from screen announcements.

Flew premium economy, well worth the extra. Much better seat size & space. Meals & snacks were lovely. Crew really pleasant. Internet is not great, not really useful for anything. Couldn't even send messages.

Everything was fine. Wish the wifi was free and included in the ticket price.

Nothing special short flight - all good - difference between 1 fudge and 2 fudge is obligation and thankfulness

Their aircraft are old and amenities lack way behind other international carriers leaving from BNE. Even in economy

Friendly staff, surprisingly good premium economy seats allowing good sleep/ snooze opportunity and very good menu.

I liked the service, the menu, and the comfort of the seats! Even tho we were seated by the bathrooms, the reclining seats and movie selection was very good, my husband and I didn’t mind at all

It’s a two prop flight so I had problems with my ears on re- entering ! But otherwise fine

Complaint is with American Airlines which delayed our flight from salt lake to Dallas reaulting in us missing our connection to Brisbane. Had to spend 24 hours in Dallas to wait for the next flight. Awful experience and ruined my wife’s birthday.

I have flown Qantas multiple times in the past it seemed this flight the plane had less seat room or the seats were way less comfortable than before. Everything else was about the same. Thanks

The old Plane had not been cleaned properly in a long time.

I got upgraded from economy to business, and the experience was outstanding

I have taken this flight many times. It is ALWAYS late. Every time there is significant delay (1-3 hours) before boarding. It’s very consistent. Even after boarding the expected landing time was delayed twice. The seats are very narrow and cramped. Food is barely editable. Considering an economy ticket often costs about $2,000 it’s one of the worst services ever.

American Airlines was their usual junk service — but at least it got us down to LA. I was more irritated that while they codeshare with Alaska Airlines in Seattle, they could not out our flight on one of these, opting for one of the small SkyWest operated American Eagle flights — and causing a 14 hour layover. Which I accepted due to a $2000 difference in airfare — that said it was irritating for a flight that usually would have cost around $100 extra, if that.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

Short flight so no food or entertainment. Good landing at SFO and on time. We were told no carryon luggage yet lots of people were puting bags in overhead compartments. The rules need to be made more clear. I was on the first leg of an international flight and this is the first time I could not have carryon luggage.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Comfortable seats and movies entertainment available. Better experience than the flight from Toronto to Denver.

Overall good experience. The flight from Toronto to Denver does not have entertainment - movies to watch.

There is not enough space between two chairs and raws.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Crammed in like cattle waited 30 mins for late connecting flight (flight didn’t wait for me for me when I missed my connection at 2 different airports on outward journey)

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

It was a lovely flight. Very attentive crew, comfortable seats, good food and entertainment. Highly recommended. Only difficulty was with their app.

Terrible. Flight was delayed for hours and we ended up arriving at our home at 4am after 20+ hours flying.

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Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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