$756 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 20/11. 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.
1 adult
1 adult, Economy

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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Flights 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

Thu, 25 Sep - Sat, 25 Oct
American Airlines Logo
15:50 - 06:01AKL-ORD
31h 11m1 stop
American Airlines Logo
19:03 - 09:25ORD-AKL
20h 22m1 stop
$1,409American Airlines
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Thu, 25 Sep - Sat, 25 Oct
American Airlines Logo
06:00 - 06:01AKL-ORD
41h 01m2 stops
American Airlines Logo
06:00 - 09:25ORD-AKL
33h 25m1 stop
$1,429American Airlines
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Thu, 25 Sep - Sat, 25 Oct
Air Canada Logo
06:35 - 15:00AKL-ORD
25h 25m2 stops
Air Canada Logo
15:40 - 16:50ORD-AKL
31h 10m2 stops
$1,499Air Canada
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Thu, 25 Sep - Sat, 25 Oct
Air Canada Logo
06:35 - 16:42AKL-ORD
27h 07m2 stops
Air Canada Logo
14:00 - 16:50ORD-AKL
32h 50m3 stops
$1,510Air Canada
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Tue, 5 Aug - Tue, 12 Aug
United Airlines Logo
20:15 - 04:51AKL-ORD
25h 36m1 stop
United Airlines Logo
16:50 - 07:10ORD-AKL
21h 20m1 stop
$1,962United Airlines
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Mon, 11 Aug - Tue, 9 Sep
United Airlines Logo
13:50 - 23:13AKL-ORD
26h 23m1 stop
United Airlines Logo
16:30 - 07:10ORD-AKL
21h 40m1 stop
$1,977United Airlines
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Mon, 18 Aug - Mon, 25 Aug
Qantas Airways Logo
06:00 - 15:55CHC-ORD
26h 55m2 stops
Qantas Airways Logo
19:03 - 15:25ORD-CHC
27h 22m2 stops
$2,047Qantas Airways
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Tue, 5 Aug - Tue, 12 Aug
Qantas Airways Logo
07:30 - 17:20AKL-ORD
26h 50m2 stops
Qantas Airways Logo
18:20 - 14:05ORD-AKL
26h 45m2 stops
$2,058Qantas Airways
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Sun, 13 Jul - Wed, 30 Jul
Air New Zealand Logo
15:55 - 23:59AKL-ORD
25h 04m1 stop
Air New Zealand Logo
09:46 - 05:30ORD-AKL
26h 44m1 stop
$2,109Air New Zealand
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Sun, 10 Aug - Sun, 17 Aug
Air New Zealand Logo
20:15 - 04:51AKL-ORD
25h 36m1 stop
Air New Zealand Logo
07:10 - 05:00ORD-AKL
28h 50m1 stop
$2,114Air New Zealand
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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?

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 $1,535 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 $2,429 and $2,309 respectively. For one-way flights, the best month to travel is February with an average price of $1,535.

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 $239.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
High seasonJune
Cheapest flight$756
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Christchurch 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $1,916. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $2,217 on average.

  • 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.

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

    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.

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?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop 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, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 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, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Reviews of the 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 485 reviews
7.4Entertainment
8.2Boarding
8.5Crew
8.0Comfort
7.3Food
Airline reviews

The 10hr flight was a comfortable as it could be in row 57. The food was just very bad….bland and soggy!

6.0 GoodAnonymous, May 2025NAN - LAX
Read more Air New Zealand reviews

The 10hr flight was a comfortable as it could be in row 57. The food was just very bad….bland and soggy!

The business class upgrade meant a good sleep on the way home after a long week away. Excellent service, great food, and comfortable seat/bed for the journey.

I love the “boarding from the back” idea - it’s so much better than the “Zones” idea that many others use. Also, the inflight wifi was a first for me! Very nice to have on a 13-hour flight!

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.

Traditional economy class. Not a full flight so spare seats. Food and drinks were good

Was bumped to a later flight because of inefficiency on part of the airline.

Touch screens were very difficult to use, generally being laggy and unresponsive- it was quite an art to get it to play the thing you wanted rather than some thing at random. Selection of films and Tv was good when touchscreen decided to finally respond.

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.

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.

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

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

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

This was an excellent experience for a very short flight.

Registered my luggage at 5pm. Arrived at JFK at 1:00 am. Worst trip ever. Never again

Really good, super comfy flight and the stewardess was great.

Air Canada never runs on time. You’re lucky if your flight is not cancelled or diverted. Worst airline in the world for gas lighting its customers.

No space in overhead bin, one cookie, 2 oz of juice - is not customer service.

Good flight, friendly crew and overall - good service on United Airlines.

Received email saying that there won’t be a seat back entertainment screen and inflight WiFi would be available. But no WiFi both ways. Say it in the email.

Somebody either kayak or Air Canada booked my flight under my preferred name Betty instead of my legal name and I almost was denied boarding my flight

flight landed late almost 1.00hr and we 4 passengers missed our connected flight to indianapolis, we need to get the hotel and taxi for the next day flight to home in indianapolis, cost us $ 300 more

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.

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Everything you need to know for your flight to Chicago

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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