$952 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
$1,630
Typical prices: $2,015-$2,721
Qantas Airways
Sun 9/12Sun 30/12
AKL - ORD • 1 stop
Cheapest one-way flight
$911
Typical prices: $1,014-$1,389
Multiple Airlines
Mon 26/2
AKL - ORD • 3 stops
Top airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
Top routes
Cheapest • 11% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 12 weeks in advance save around 44% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 21% price drop
Most popular
Good to know
+1
Good to know
+1
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We hope you enjoy your trip to Chicago!
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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

Wed, 9 Dec - Wed, 30 Dec
Qantas Airways Logo
13:20 - 21:11AKL  Auckland Intl-ORD Chicago O'Hare Intl
26h 51m1 stop Dallas/Fort Worth
Qantas Airways Logo
06:00 - 09:55ORD  Chicago O'Hare Intl-AKL Auckland Intl
32h 55m1 stop Los Angeles
$1,630Qantas Airways
Thu, 5 Nov - Mon, 9 Nov
American Airlines Logo
06:00 - 06:05AKL  Auckland Intl-ORD Chicago O'Hare Intl
43h 05m2 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
$1,630American Airlines
Thu, 5 Nov - Mon, 9 Nov
American Airlines Logo
06:00 - 05:02AKL  Auckland Intl-ORD Chicago O'Hare Intl
42h 02m2 stops Sydney Kingsford Smith Los Angeles
American Airlines Logo
18:10 - 09:10ORD  Chicago O'Hare Intl-AKL Auckland Intl
68h 00m2 stops New York LaGuardia Dallas/Fort Worth
$1,630American Airlines
Wed, 9 Dec - Wed, 30 Dec
Qantas Airways Logo
13:20 - 21:11AKL  Auckland Intl-ORD Chicago O'Hare Intl
26h 51m1 stop Dallas/Fort Worth
Qantas Airways Logo
06:00 - 09:55ORD  Chicago O'Hare Intl-AKL Auckland Intl
32h 55m1 stop Los Angeles
$1,653Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
American Airlines Logo
09:40 - 23:00WLG  Wellington-ORD Chicago O'Hare Intl
32h 20m2 stops Auckland Intl Dallas/Fort Worth
American Airlines Logo
06:59 - 17:20ORD  Chicago O'Hare Intl-WLG Wellington
39h 21m2 stops Los Angeles Auckland Intl
$1,827American Airlines
Tue, 10 Nov - Wed, 18 Nov
Air New Zealand Logo
20:20 - 20:35AKL  Auckland Intl-ORD Chicago O'Hare Intl
19h 15m1 stop Los Angeles
Air New Zealand Logo
06:00 - 05:50ORD  Chicago O'Hare Intl-AKL Auckland Intl
28h 50m1 stop Los Angeles
$1,971Air New Zealand
Tue, 10 Nov - Tue, 17 Nov
Air New Zealand Logo
20:20 - 00:59AKL  Auckland Intl-ORD Chicago O'Hare Intl
23h 39m1 stop Los Angeles
Air New Zealand Logo
13:00 - 05:50ORD  Chicago O'Hare Intl-AKL Auckland Intl
21h 50m1 stop Los Angeles
$1,971Air New Zealand
Mon, 2 Nov - Mon, 9 Nov
Air New Zealand Logo
19:50 - 23:26AKL  Auckland Intl-ORD Chicago O'Hare Intl
22h 36m1 stop Houston George Bush Intcntl
Air New Zealand Logo
16:35 - 09:10ORD  Chicago O'Hare Intl-AKL Auckland Intl
21h 35m1 stop San Francisco
$1,971Air New Zealand
Wed, 11 Nov - Wed, 18 Nov
Qantas Airways Logo
06:50 - 17:00AKL  Auckland Intl-ORD Chicago O'Hare Intl
29h 10m2 stops Brisbane Los Angeles
Qantas Airways Logo
16:53 - 09:10ORD  Chicago O'Hare Intl-AKL Auckland Intl
21h 17m1 stop Dallas/Fort Worth
$2,087Qantas Airways
Wed, 11 Nov - Wed, 18 Nov
Qantas Airways Logo
06:50 - 17:00AKL  Auckland Intl-ORD Chicago O'Hare Intl
29h 10m2 stops Brisbane Los Angeles
Qantas Airways Logo
15:25 - 14:05ORD  Chicago O'Hare Intl-AKL Auckland Intl
27h 40m2 stops Los Angeles Sydney Kingsford Smith
$2,197Qantas Airways
Booking Insights

Price, demand, and travel trends for New Zealand to Chicago flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights from New Zealand to Chicago with more confidence.

What is the cheapest flight to Chicago?

Auckland to Chicago is the cheapest route at $1,630 return, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.

How much is a flight to Chicago?

A return flight to Chicago costs $2,321 on average, based on data over the past 12 months on KAYAK. Return fares from Wellington average $2,166, while Auckland runs a bit higher at $2,224.

What is the cheapest day to fly to Chicago?

Monday is the cheapest day to fly to Chicago at $2,180 return on average over the past 12 months on KAYAK. Thursday is the most expensive at $2,594.

What is the cheapest month to fly to Chicago?

•February is the cheapest month to fly to Chicago with an average price of $1,832 return.
•May ($2,717) and June ($2,555) are the most expensive.
•Based on KAYAK data over the past 12 months.

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

Evening flights to Chicago are the cheapest at $2,390 return on average. Night flights are the most expensive at $2,523.

What is a good deal for flights to Chicago?

Flights under $2,015 are considered a good deal. 25% of KAYAK users found return flights to Chicago at or below these prices, with the lowest fares from:
•Wellington $1,919
•Auckland $1,975.

When are flights to Chicago the cheapest?

Flights to Chicago are cheapest 12 weeks before departure. Booking in this window typically costs about 44% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for flights to Chicago

Low season

March

Cheapest flight

$911
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly (2% more expensive on average)
Flights from Auckland to Chicago O'Hare Intl Airport

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

Your questions about flights to Chicago, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Chicago is a good deal?

    A good deal on a flight to Chicago is around $2,015 return. This fare is in the lowest 25% of return flight prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • Which airports serve Chicago?

    Flights to Chicago arrive at: Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • How expensive are last-minute flights to Chicago?

    Last-minute fares to Chicago – booked within 2 weeks of departure – run 7% above the average return fare of $2,321.

  • What is the difference between the most popular and the most frequent airline at Chicago?

    Qantas Airways operates the most flights from New Zealand to Chicago at 0 per week, while Air New Zealand is the airline most often selected by KAYAK users searching for flights from New Zealand to Chicago. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80.5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

Your guide to booking Chicago flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Chicago, aim to book around 12 weeks before you fly. That window historically saves about 44% versus last-minute pricing based on KAYAK booking data over the last 12 months.
  • For flights to Chicago, recent KAYAK data shows that stronger deals tend to be around $2,015 return. If you see a fare below that threshold, it's a good deal – book before the price climbs back up.
  • If you can choose when to go, aim to travel to Chicago in February. Return fares historically average $1,832 that month – typically the cheapest month to travel based on the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to afternoon to save up to $133 per return. Afternoon flights to Chicago average $2,390 compared to $2,523 for evening flights. See the time-of-day chart above for the full breakdown.
  • Once you arrive in Chicago, a great place to start is River North. It is popular with first-time visitors and can give you a good feel for the area.

Reviews of the top 3 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 670 reviews
8.2Boarding
8.5Crew
7.5Food
7.4Entertainment
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
Read more Air New Zealand reviews

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.

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

After having bad experience last time This time they were very good

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

The counter person at the gate was rude and demeaning, to the point that I wouldn't fly this airline again.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

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