$869 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return fare
$1,889
Typical prices: $1,391-$1,896
United Airlines
Thu 22/10Sat 24/10
AKL - ORD • 2 stops
Cheapest one-way flight
$869
Typical prices: $960-$1,236
Multiple Airlines
Mon 2/11
AKL - ORD • 3 stops
When to travel
Cheapest • 27% price drop
Most popular
Good to know
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Flight Deals

Cheap Flights to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Thu, 22 Oct - Sat, 24 Oct
United Airlines Logo
20:15 - 07:55AKL  Auckland Intl-ORD Chicago O'Hare Intl
29h 40m2 stops Los Angeles Houston George Bush Intcntl
United Airlines Logo
07:00 - 06:00ORD  Chicago O'Hare Intl-AKL Auckland Intl
29h 00m1 stop Los Angeles
$1,889United Airlines
Thu, 22 Oct - Sat, 24 Oct
United Airlines Logo
19:50 - 09:09AKL  Auckland Intl-ORD Chicago O'Hare Intl
31h 19m1 stop Houston George Bush Intcntl
United Airlines Logo
08:50 - 06:00ORD  Chicago O'Hare Intl-AKL Auckland Intl
27h 10m1 stop Los Angeles
$1,889United Airlines
Thu, 8 Oct - Thu, 22 Oct
Multiple Airlines Logo
16:15 - 06:34AKL  Auckland Intl-ORD Chicago O'Hare Intl
32h 19m2 stops Papeete Faaa Los Angeles
Multiple Airlines Logo
20:01 - 17:55ORD  Chicago O'Hare Intl-AKL Auckland Intl
51h 54m2 stops Los Angeles Sydney Kingsford Smith
$1,992Multiple Airlines
Sun, 20 Dec - Wed, 30 Dec
Qantas Airways Logo
15:50 - 12:21AKL  Auckland Intl-ORD Chicago O'Hare Intl
39h 31m1 stop Los Angeles
Qantas Airways Logo
19:01 - 09:25ORD  Chicago O'Hare Intl-AKL Auckland Intl
19h 24m1 stop Dallas/Fort Worth
$2,027Qantas Airways
Thu, 5 Nov - Mon, 9 Nov
American Airlines Logo
07:30 - 16:05AKL  Auckland Intl-ORD Chicago O'Hare Intl
27h 35m2 stops Sydney Kingsford Smith Los Angeles
American Airlines Logo
20:00 - 09:10ORD  Chicago O'Hare Intl-AKL Auckland Intl
66h 10m2 stops New York LaGuardia Dallas/Fort Worth
$2,179American Airlines
Thu, 5 Nov - Mon, 9 Nov
American Airlines Logo
07:30 - 16:05AKL  Auckland Intl-ORD Chicago O'Hare Intl
27h 35m2 stops Sydney Kingsford Smith Los Angeles
American Airlines Logo
20:00 - 09:10ORD  Chicago O'Hare Intl-AKL Auckland Intl
66h 10m2 stops New York LaGuardia Dallas/Fort Worth
$2,182American Airlines
Mon, 19 Oct - Sat, 24 Oct
Air New Zealand Logo
19:50 - 00:55AKL  Auckland Intl-ORD Chicago O'Hare Intl
23h 05m1 stop San Francisco
Air New Zealand Logo
22:15 - 05:45ORD  Chicago O'Hare Intl-AKL Auckland Intl
37h 30m1 stop Houston George Bush Intcntl
$2,229Air New Zealand
Wed, 21 Oct - Thu, 5 Nov
Air New Zealand Logo
20:15 - 22:55AKL  Auckland Intl-ORD Chicago O'Hare Intl
20h 40m1 stop Los Angeles
Air New Zealand Logo
13:30 - 09:10ORD  Chicago O'Hare Intl-AKL Auckland Intl
24h 40m1 stop San Francisco
$2,258Air New Zealand
Mon, 12 Oct - Mon, 19 Oct
Qantas Airways Logo
06:20 - 20:38CHC  Christchurch-ORD Chicago O'Hare Intl
32h 18m2 stops Melbourne Dallas/Fort Worth
Qantas Airways Logo
15:20 - 14:45ORD  Chicago O'Hare Intl-CHC Christchurch
29h 25m2 stops Los Angeles Melbourne
$2,324Qantas Airways
Wed, 7 Oct - Wed, 14 Oct
Qantas Airways Logo
06:00 - 18:35CHC  Christchurch-ORD Chicago O'Hare Intl
30h 35m2 stops Sydney Kingsford Smith Dallas/Fort Worth
Qantas Airways Logo
18:55 - 00:20ORD  Chicago O'Hare Intl-CHC Christchurch
35h 25m2 stops Los Angeles Sydney Kingsford Smith
$2,335Qantas Airways
Booking Insights

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 month to fly to Chicago?

The cheapest month for flights to Chicago is February, where tickets cost $1,569 on average for return flights. On the other hand, the most expensive months are May and June, where the average cost of tickets from New Zealand is $2,622 and $2,542 respectively. For one-way flights, the best month to travel is October with an average price of $1,015.

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 O'Hare Intl Airport (ORD), with an average flight price of $757.

Good to know – Book Cheap Chicago Plane Tickets

Low season

April

Cheapest flight

$869
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly (2% 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

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 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.

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.

Reviews of the top 4 airlines flying to Chicago

 
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 665 reviews
7.5Food
7.9Comfort
8.2Boarding
7.4Entertainment
8.5Crew
Airline reviews

mechanical issue, so delayed take-off (hence the low boarding rating) and made a number of people miss their connecting flight. Also took a long time to get our checked baggage. I luckily made mine with 5 minutes to spare, but it was nerve-racking.

8.0 ExcellentAnonymous, Aug 2026
Read more Air New Zealand reviews

mechanical issue, so delayed take-off (hence the low boarding rating) and made a number of people miss their connecting flight. Also took a long time to get our checked baggage. I luckily made mine with 5 minutes to spare, but it was nerve-racking.

The flight was smooth and on time. Entertainment options were lacking and there was no food, other than some very boring snacks.

A better selection of entertainment would have been nice. I found nothing that appealed to me as a middle-aged traveler. The flight attendants were gracious, helpful, and attentive. It also would have been nice to have more bathrooms as the flight was full and the plane was big.

The Premium Economy seats were very comfortable and the food was quite tasty. I did not use the entertainment system, but I was able to charge my phone and tablet with the seatback connection.

Air New Zealand over sold our flight and tried to bump us to yesterday. After several calls we got booked to United about 6 hrs before our original flight. No apologies!

Please add more Bollywood movies and recent movies to the entertainment.

Flight was delayed by 2 hours. Got lucky that i had a long connection, else would have certainly missed my connecting flight. Food is just okay, specially the breakfast is worse . Asked for water 30 mins before landing, the response is that we are landing so everything is packed . I guess traveling in economy that’s what we get. Probably business class passengers would get a different answer. Only good thing is that wifi service is available from auckland to lax for most part Next time will try united or American and then compare.

Great except paying $240 usd for 2 pounds over on a checked luggage. Outrageous.

Service was excellent and they’re very helpful and nice

Carring crew, nice ambiance of the cabin, comfortable beds, good food well served. We liked everything.

Overall, it was a very good experience. I would have given it a 10/10, especially based on our flight from SFO to Melbourne. The cabin crew on that flight were wonderful and incredibly attentive. They took extra care when setting up our beds so we could sleep comfortably without being disturbed. Dinner was served promptly and smoothly. I woke up quite late, when the flight was already preparing for landing, and the crew still made sure I was taken care of. They brought me English tea in a proper cup, and when it was time to prepare the cabin for landing, they thoughtfully transferred it into a takeaway cup so I could continue enjoying it along with some breakfast. Those small, thoughtful gestures made the long flight feel much more comfortable and special. The service from the SFO to Melbourne crew was truly excellent.

Having the computer outage compounded by delayed takeoff while waiting for aircrew (who were also delayed) resulted in me missing my int’l flight

We had a cancellation due to weather, but the American Airlines staff was very helpful. Once we got on a plane, the trip was great.

Great food and good entertainment options for the long flight.

Loved the food and beverages available, spacious economy class, excellent entertainment

We booked with Qantas instead of Delta and we instead flew on American Airlines. American is not our favorite to go on. No leg room and the width of seats are a joke. Your are packed like sardines on American flights.

they ran out of fruit for breakfast and so I just had a yogurt instead. other than that the flight was good

Poor! This flight was delayed 14 hours. There was no assistance in helping customers find other routes to their destination, nor any other kind of support. It was a chaotic experience. I'm not likely to fly with AA going forward.

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 a positive experience. As long as you are not connecting-I found the discount offered by Kayak and the customer service to be very good.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

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.

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.

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

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago