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Everything you should know
Flight Deals
Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.
Recent return flight deals to Chicago
Tue, 16 Mar - Fri, 26 Mar
06:00 - 19:45CHC Christchurch-ORD Chicago O'Hare Intl
31h 45m2 stops Sydney Kingsford Smith Los Angeles
13:37 - 15:25ORD Chicago O'Hare Intl-CHC Christchurch
31h 48m2 stops San Francisco Sydney Kingsford Smith
$1,821Qantas Airways
Sat, 30 Jan - Tue, 16 Feb
13:20 - 19:59AKL Auckland Intl-ORD Chicago O'Hare Intl
25h 39m1 stop Dallas/Fort Worth
13:23 - 09:55ORD Chicago O'Hare Intl-AKL Auckland Intl
25h 32m1 stop Los Angeles
$1,853Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,860American Airlines
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,871American Airlines
Sat, 30 Jan - Tue, 16 Feb
07:30 - 16:54AKL Auckland Intl-ORD Chicago O'Hare Intl
28h 24m2 stops Sydney Kingsford Smith Los Angeles
12:11 - 09:55ORD Chicago O'Hare Intl-AKL Auckland Intl
26h 44m1 stop Los Angeles
$1,871Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,874American Airlines
Sat, 30 Jan - Tue, 16 Feb
06:50 - 14:12AKL Auckland Intl-ORD Chicago O'Hare Intl
26h 22m2 stops Brisbane Dallas/Fort Worth
16:54 - 18:00ORD Chicago O'Hare Intl-AKL Auckland Intl
30h 06m2 stops Dallas/Fort Worth Sydney Kingsford Smith
$1,890Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,896American Airlines
Tue, 16 Mar - Fri, 26 Mar
13:15 - 18:50CHC Christchurch-ORD Chicago O'Hare Intl
23h 35m1 stop San Francisco
14:15 - 09:25ORD Chicago O'Hare Intl-CHC Christchurch
25h 10m2 stops Houston George Bush Intcntl Auckland Intl
$2,308Air New Zealand
Thu, 10 Dec - Thu, 24 Dec
15:50 - 19:05AKL Auckland Intl-ORD Chicago O'Hare Intl
22h 15m1 stop San Francisco
05:30 - 05:45ORD Chicago O'Hare Intl-AKL Auckland Intl
29h 15m1 stop Houston George Bush Intcntl
$2,404Air New Zealand
Recent one-way flight deals to Chicago
Mon, 1 Mar
14:50 - 07:05AKL Auckland Intl-ORD Chicago O'Hare Intl
35h 15m2 stops Nadi Los Angeles
$891Multiple Airlines
Mon, 1 Mar
14:50 - 17:01AKL Auckland Intl-ORD Chicago O'Hare Intl
45h 11m3 stops Nadi Los Angeles Seattle/Tacoma Intl
$1,005Multiple Airlines
Sat, 30 Jan
14:20 - 00:26CHC Christchurch-ORD Chicago O'Hare Intl
29h 06m3 stops Auckland Intl Los Angeles Denver Intl
$1,037Multiple Airlines
Thu, 3 Dec
07:30 - 00:53AKL Auckland Intl-ORD Chicago O'Hare Intl
36h 23m3 stops Sydney Kingsford Smith Los Angeles Denver Intl
$1,044Multiple Airlines
Fri, 29 Jan
17:05 - 00:26CHC Christchurch-ORD Chicago O'Hare Intl
50h 21m3 stops Auckland Intl Los Angeles Denver Intl
$1,056Multiple Airlines
Sun, 31 Jan
06:15 - 06:10CHC Christchurch-ORD Chicago O'Hare Intl
42h 55m3 stops Auckland Intl Los Angeles Las Vegas Harry Reid Intl
$1,079Multiple Airlines
Tue, 24 Nov
07:30 - 05:10AKL Auckland Intl-ORD Chicago O'Hare Intl
40h 40m3 stops Sydney Kingsford Smith Los Angeles Las Vegas Harry Reid Intl
$1,081Multiple Airlines
Fri, 18 Dec
21:50 - 07:02CHC Christchurch-ORD Chicago O'Hare Intl
52h 12m3 stops Auckland Intl Papeete Faaa Los Angeles
$1,083Multiple Airlines
Thu, 5 Nov
20:20 - 00:59AKL Auckland Intl-ORD Chicago O'Hare Intl
23h 39m1 stop Los Angeles
$1,207Air New Zealand
Thu, 3 Dec
15:50 - 05:59AKL Auckland Intl-ORD Chicago O'Hare Intl
33h 09m1 stop San Francisco
$1,222Air New Zealand
Recent last minute flight deals to Chicago
Mon, 2 Nov - Sun, 15 Nov
14:55 - 12:30AKL Auckland Intl-ORD Chicago O'Hare Intl
40h 35m1 stop Hong Kong Intl
14:10 - 13:25ORD Chicago O'Hare Intl-AKL Auckland Intl
28h 15m1 stop Hong Kong Intl
$2,308Cathay Pacific
Tue, 3 Nov - Tue, 10 Nov
19:50 - 19:55AKL Auckland Intl-ORD Chicago O'Hare Intl
19h 05m1 stop Houston George Bush Intcntl
12:42 - 09:10ORD Chicago O'Hare Intl-AKL Auckland Intl
25h 28m1 stop San Francisco
$2,379Air New Zealand
Mon, 2 Nov - Sun, 15 Nov
14:55 - 12:30AKL Auckland Intl-ORD Chicago O'Hare Intl
40h 35m1 stop Hong Kong Intl
06:44 - 13:25ORD Chicago O'Hare Intl-AKL Auckland Intl
35h 41m2 stops New York John F Kennedy Intl Hong Kong Intl
$2,388Multiple Airlines
Tue, 3 Nov - Tue, 10 Nov
14:55 - 12:30AKL Auckland Intl-ORD Chicago O'Hare Intl
40h 35m1 stop Hong Kong Intl
14:10 - 00:25ORD Chicago O'Hare Intl-AKL Auckland Intl
39h 15m2 stops Hong Kong Intl Sydney Kingsford Smith
$2,420Multiple Airlines
Tue, 3 Nov - Tue, 10 Nov
16:05 - 05:02AKL Auckland Intl-ORD Chicago O'Hare Intl
31h 57m2 stops Papeete Faaa Los Angeles
06:29 - 13:40ORD Chicago O'Hare Intl-AKL Auckland Intl
36h 11m2 stops Los Angeles Papeete Faaa
$2,449Air Tahiti Nui
Tue, 3 Nov - Wed, 11 Nov
19:50 - 19:55AKL Auckland Intl-ORD Chicago O'Hare Intl
19h 05m1 stop Houston George Bush Intcntl
16:01 - 09:10ORD Chicago O'Hare Intl-AKL Auckland Intl
22h 09m1 stop San Francisco
$2,450Air New Zealand
Wed, 4 Nov - Tue, 10 Nov
19:55 - 21:45AKL Auckland Intl-ORD Chicago O'Hare Intl
20h 50m1 stop San Francisco
16:35 - 09:10ORD Chicago O'Hare Intl-AKL Auckland Intl
21h 35m1 stop San Francisco
$2,450Air New Zealand
Tue, 3 Nov - Mon, 9 Nov
20:20 - 20:35AKL Auckland Intl-ORD Chicago O'Hare Intl
19h 15m1 stop Los Angeles
14:30 - 09:10ORD Chicago O'Hare Intl-AKL Auckland Intl
23h 40m1 stop San Francisco
$2,450Air New Zealand
Wed, 4 Nov - Wed, 11 Nov
19:55 - 22:29AKL Auckland Intl-ORD Chicago O'Hare Intl
21h 34m1 stop San Francisco
14:00 - 05:00ORD Chicago O'Hare Intl-AKL Auckland Intl
20h 00m1 stop Los Angeles
$2,450Air New Zealand
Mon, 2 Nov - Tue, 10 Nov
20:20 - 22:00AKL Auckland Intl-ORD Chicago O'Hare Intl
20h 40m1 stop Los Angeles
18:20 - 09:10ORD Chicago O'Hare Intl-AKL Auckland Intl
19h 50m1 stop San Francisco
$2,450Air New Zealand
All return flight deals to Chicago
Tue, 16 Mar - Fri, 26 Mar
06:00 - 19:45CHC Christchurch-ORD Chicago O'Hare Intl
31h 45m2 stops Sydney Kingsford Smith Los Angeles
13:37 - 15:25ORD Chicago O'Hare Intl-CHC Christchurch
31h 48m2 stops San Francisco Sydney Kingsford Smith
$1,821Qantas Airways
Sat, 30 Jan - Tue, 16 Feb
13:20 - 19:59AKL Auckland Intl-ORD Chicago O'Hare Intl
25h 39m1 stop Dallas/Fort Worth
13:23 - 09:55ORD Chicago O'Hare Intl-AKL Auckland Intl
25h 32m1 stop Los Angeles
$1,853Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,860American Airlines
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,871American Airlines
Sat, 30 Jan - Tue, 16 Feb
07:30 - 16:54AKL Auckland Intl-ORD Chicago O'Hare Intl
28h 24m2 stops Sydney Kingsford Smith Los Angeles
12:11 - 09:55ORD Chicago O'Hare Intl-AKL Auckland Intl
26h 44m1 stop Los Angeles
$1,871Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,874American Airlines
Sat, 30 Jan - Tue, 16 Feb
06:50 - 14:12AKL Auckland Intl-ORD Chicago O'Hare Intl
26h 22m2 stops Brisbane Dallas/Fort Worth
16:54 - 18:00ORD Chicago O'Hare Intl-AKL Auckland Intl
30h 06m2 stops Dallas/Fort Worth Sydney Kingsford Smith
$1,890Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
09:40 - 05:03WLG Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
17:59 - 17:20ORD Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,896American Airlines
Tue, 16 Mar - Fri, 26 Mar
13:15 - 18:50CHC Christchurch-ORD Chicago O'Hare Intl
23h 35m1 stop San Francisco
14:15 - 09:25ORD Chicago O'Hare Intl-CHC Christchurch
25h 10m2 stops Houston George Bush Intcntl Auckland Intl
$2,308Air New Zealand
Thu, 10 Dec - Thu, 24 Dec
15:50 - 19:05AKL Auckland Intl-ORD Chicago O'Hare Intl
22h 15m1 stop San Francisco
05:30 - 05:45ORD Chicago O'Hare Intl-AKL Auckland Intl
29h 15m1 stop Houston George Bush Intcntl
$2,404Air New Zealand
Booking Insights
Price, demand, and travel trends for flights to Chicago
Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
What is the cheapest flight to Chicago?
Christchurch to Chicago is the cheapest route at $1,821 return, found in the past 5 days on KAYAK. Auckland to Chicago is the most popular connection with return deals from $1,853.
How much is a flight to Chicago?
Average and cheapest price for all return flights to Chicago from each origin found by users searching on KAYAK in the last 12 months.On average, a return flight from New Zealand to Chicago costs $2,391, based on KAYAK data over the past 12 months. Return fares from Wellington average $2,161, while Auckland runs a bit higher at $2,385.
What is the cheapest day to fly to Chicago?
Saturday is the cheapest day to fly to Chicago at $2,223 return on average over the past 12 months on KAYAK. Friday is the most expensive at $2,602.
What is the cheapest month to fly to Chicago?
To calculate monthly average prices, KAYAK takes all prices for each month over the last 12 months for flights to Chicago, removes the top 0.1% to account for outliers, then takes the median of all values for each month.•February is the cheapest month to fly to Chicago with an average price of $1,839 return.
•May ($2,818) and June ($2,625) are the most expensive.
Based on KAYAK data over the past 12 months.What is the cheapest time of day to fly to Chicago?
Average price for all return flights depending on time of departure, seen by users on KAYAK in the last 12 months.Night flights to Chicago are the cheapest at $2,000 return on average. Evening flights are the most expensive at $2,489.
What is a good deal for flights to Chicago?
Flights under $2,093 are considered a good deal. 25% of KAYAK users found return flights to Chicago at or below these prices, with the lowest fares from:
•Auckland $2,048
•Wellington $2,073.
Key details for flights to Chicago
Low season | March |
|---|---|
High season | August |
Cheapest flight | $891 |
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.
Your questions about flights to Chicago, answered
Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.
Your guide to booking Chicago flights
From booking to airport arrival, find tips to help you plan your flight with more confidence.Reviews of the top 3 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.
8.0
Air New ZealandOverall score based on 679 reviews
7.4Food
7.4Entertainment
8.5Crew
8.2Boarding
7.9Comfort
Airline reviews
Premium economy seats and food we're very nice although the price could be more affordable so we can do it more often.
10.0 ExcellentSharon, Sept 2026
Premium economy seats and food we're very nice although the price could be more affordable so we can do it more often.
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.
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.
I had bad experience with United airline. No live rep, they only have AI that respond to customers concern
Flight and crew were great. Need more legroom and do not allow seats to recline.
We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.
Just sat on the run way after we arrived early
The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights
Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.
Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol
It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.
Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.
The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.
Travelling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsPortage
Hammond
Benton Harbor
New Buffalo
More options for your flight to Chicago
Complete your trip to Chicago with a hotel stay or car hire
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.
Flights from local origins to Chicago
Flights from all regions of New Zealand to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from Auckland to Chicagofrom $1,853
Flights from Christchurch to Chicagofrom $2,591
Flights from Wellington to Chicagofrom $1,785
Choose which airport to fly into in Chicago
Flights to other airports in Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to Chicago O'Hare Intl Airportfrom $1,785
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.