$802 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 16/9. 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
 Logo
08:00 - 11:36AKL-ORD
44h 36m2 stops
 Logo
08:37 - 06:00ORD-AKL
28h 23m1 stop
$1,718
Find Deal
Tue, 6 May - Tue, 13 May
 Logo
08:00 - 11:36AKL-ORD
44h 36m2 stops
 Logo
08:37 - 06:00ORD-AKL
28h 23m1 stop
$1,738
Find Deal
Tue, 6 May - Mon, 12 May
Qantas Airways Logo
06:45 - 17:12AKL-ORD
27h 27m2 stops
Qantas Airways Logo
17:38 - 14:05ORD-AKL
27h 27m2 stops
$2,072Qantas Airways
Find Deal
Tue, 6 May - Tue, 13 May
Qantas Airways Logo
13:25 - 23:59AKL-ORD
27h 34m2 stops
Qantas Airways Logo
17:52 - 14:05ORD-AKL
27h 13m2 stops
$2,075Qantas Airways
Find Deal
Thu, 29 May - Mon, 9 Jun
Air Canada Logo
19:45 - 06:19AKL-ORD
27h 34m1 stop
Air Canada Logo
15:35 - 14:55ORD-AKL
30h 20m2 stops
$2,098Air Canada
Find Deal
Sun, 1 Jun - Mon, 9 Jun
Air Canada Logo
19:45 - 06:19AKL-ORD
27h 34m1 stop
Air Canada Logo
15:35 - 23:30ORD-AKL
38h 55m2 stops
$2,146Air Canada
Find Deal
Sun, 1 Jun - Wed, 11 Jun
Air New Zealand Logo
20:15 - 11:57AKL-ORD
32h 42m1 stop
Air New Zealand Logo
21:40 - 06:00ORD-AKL
39h 20m1 stop
$2,429Air New Zealand
Find Deal
Thu, 29 May - Mon, 9 Jun
United Airlines Logo
13:50 - 14:55AKL-ORD
18h 05m1 stop
United Airlines Logo
16:20 - 07:10ORD-AKL
21h 50m2 stops
$2,452United Airlines
Find Deal
Mon, 2 Jun - Tue, 10 Jun
Air New Zealand Logo
20:15 - 23:04AKL-ORD
19h 49m1 stop
Air New Zealand Logo
15:51 - 06:00ORD-AKL
21h 09m1 stop
$2,462Air New Zealand
Find Deal
Sun, 1 Jun - Tue, 10 Jun
United Airlines Logo
13:50 - 19:56AKL-ORD
23h 06m2 stops
United Airlines Logo
11:23 - 07:10ORD-AKL
26h 47m2 stops
$2,481United Airlines
Find Deal
Thu, 15 May - Thu, 22 May

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 $2,042. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $2,362 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 $1,736 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 $2,517 and $2,453 respectively. For one-way flights, the best month to travel is February with an average price of $1,736.

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 22 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 $412.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

High season

July

Cheapest flight

$802
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (5% more expensive 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 $1,002. The cheapest price found on KAYAK in the last 2 weeks cost $938 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, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 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.
7.9
Air New ZealandOverall score based on 458 reviews
7.2Food
7.4Entertainment
8.5Crew
8.0Comfort
8.2Boarding
Airline reviews

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

10.0 ExcellentSandra, Mar 2025NSN - AKL
Read more Air New Zealand reviews

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

The flight we had booked was cancelled due to bad weather conditions, but we were lucky to arrive at the airport quite early and got a seat on an earlier flight. The flight was mostly nice, but there were some hefty turbulences towards Queenstown. One of the passengers behaved hysterically. It would have been great if the crew had done something to calm her.

Sitting in an aisle seat equals getting hit by food cart and spilled on multiple times Food: gross and minimalistic Crew: frumpy and kurt Sound on multiple entertainment platforms poor Not an earplug problem, system soundboard poor

Major hassle with the weight of carryon luggage Having to repack bags at airport Not an issue in most of world Ridiculous issue considering the 400 pound gentleman sitting behind us

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

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.

Wheelchair assistance to move through the terminals and to/from the plane door was excellent. No vegan snack on the flight, only something with salami and cheese in it.

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 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.

same as previous comments. i hate being on a plane that long. no problems w/anything else.

nothing to complain about w/the food, and professionalism of the crew. i just cant stand being on a flight for that long of a time.

Everything was great from the staff to the seats and food. The plane was timely taking off and landing.. I couldn't have asked for a better experience (especially on such a long flight)

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.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

Flight was cancelled around 45 -1hr minutes before scheduled take off time due to mechanical issues we hadn’t even boarded yet. Had to reroute to Orlando so someone had to drive 2 1/2 to come and get me… the alternative was go through Toronto and get a later flight which didn’t work for my schedule. The flight attendants barely gave anyone a smile…not the same as flying when a client/passenger was important. Very disappointed. By the way I have never ever made a complaint online about any company with feedback…even when I probably should have. The only good experience was the boarding desk associates who were very professional and got me on another flight with my checked bags…very nice team.

Actually as my experience with air Canada from Canada to Newark it was crazy for me because it was a lot of delays which for me it shouldn’t be like that, but I was able to coup with it so that was my experience I hope next time they will do good on that thanks.

Boarding was challenging as we had to use the stairs from the tarmac. Stairs are okay but a roller bag makes it challenging.

Ensure prepaid food arrangements are appropriately understood by flight crew of who purchased and who did not

All was fine. Weather was a bit stormy, but nothing kayak can do about that! 😊

I paid for a comfort class seat and was seated in economy.

Once again our Air Canada flight was delayed! I'm hopeful competition arrives with other airlines soon and maybe they will make a better effort to be on time!

My plane was cancelled and had to be rebook for the evening was not happy.

The flight was cancelled and we had to rebook on Porter to make our cruise the next day. Air Canada has not compensated. We won’t be flying with them again. This is the second time this has happened. Also the return flight was delayed 2 hours who knows why.

Mixed experienced. Nice staff. Spacious 787 better than cramped Airbus, though my seat was broken. The bad: Way overpriced ticket and charged for food despite 6 hr flight.

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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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