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$1,003 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 18/9. 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.
1 adult
Mon 27/5
Mon 3/6

Search 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
In the last 7 days, travellers have searched 44,335,567 times on KAYAK, and here's why:

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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 round-trip 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 and deals for you by selecting your travel dates.
Choose your dates
15:50 - 12:40CHC-ORD
38h 50m2 stops
06:00 - 15:25ORD-CHC
39h 25m2 stops
$1,927American Airlines
Find Deal
Thu, 17 Oct - Mon, 21 Oct
15:50 - 14:19CHC-ORD
40h 29m2 stops
13:20 - 15:25ORD-CHC
32h 05m2 stops
$1,954American Airlines
Find Deal
Thu, 17 Oct - Mon, 21 Oct
06:35 - 14:21AKL-ORD
24h 46m2 stops
15:40 - 16:50ORD-AKL
32h 10m2 stops
$2,019Air Canada
Find Deal
Fri, 9 Aug - Sun, 18 Aug
15:55 - 06:04WLG-ORD
55h 09m3 stops
17:03 - 14:50ORD-WLG
28h 47m2 stops
$2,071Qantas Airways
Find Deal
Wed, 24 Jul - Mon, 29 Jul
19:45 - 14:10AKL-ORD
35h 25m2 stops
21:15 - 05:30ORD-AKL
39h 15m1 stop
$2,075United Airlines
Find Deal
Fri, 9 Aug - Sun, 18 Aug
15:55 - 18:55AKL-ORD
20h 00m1 stop
21:05 - 06:00ORD-AKL
39h 55m1 stop
$2,080United Airlines
Find Deal
Sat, 24 Aug - Sat, 14 Sep
00:25 - 06:23AKL-ORD
22h 58m1 stop
06:30 - 06:00ORD-AKL
30h 30m1 stop
$2,134Air New Zealand
Find Deal
Tue, 10 Sep - Sun, 15 Sep
11:25 - 19:33CHC-ORD
26h 08m3 stops
15:00 - 14:50ORD-CHC
29h 50m2 stops
$2,854Qantas Airways
Find Deal
Thu, 17 Oct - Mon, 21 Oct
13:50 - 00:50AKL-ORD
28h 00m1 stop
14:10 - 06:00ORD-AKL
22h 50m1 stop
$2,891Air New Zealand
Find Deal
Thu, 20 Jun - Sat, 20 Jul
06:35 - 19:58AKL-ORD
30h 23m2 stops
13:00 - 15:05ORD-AKL
33h 05m3 stops
$12,998Air Canada
Find Deal
Thu, 27 Jun - Mon, 8 Jul

Flights to Chicago - Travel Insights & Trends

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 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 Friday where tickets can be as cheap as $2,058. On the other hand, the most expensive day to fly is Monday, where prices are $2,244 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 October, where tickets cost $1,969 on average for one-way flights. On the other hand, the most expensive months are December and July, where the average cost of tickets from New Zealand is $2,606 and $2,444 respectively. For return trips, the best month to travel is October with an average price of $1,969.

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

The average price for all 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 morning, when flights cost $2,062 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 $2,183.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 87 days 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 O'Hare Intl Airport, with an average flight price of $597.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 86% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Auckland, which takes 24h 46m, Christchurch, which takes 24h 55m, and Wellington, which takes 26h 01m.

Good to know

Low season

February

High season

June

Cheapest flight

$1,003
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly and prices are also 0% lower 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 $1,574. The cheapest price found on KAYAK in the last 2 weeks cost $896 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.

  • Which airline offers the most flights to Chicago?

    Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 5,061 per week, followed by American Airlines with 3,461 flights per week.

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, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to New Zealand

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Top 5 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.
8.2
Air New ZealandOverall score based on 647 reviews
8.8crew
8.4boarding
7.7food
8.1comfort
7.9entertainment
Airline reviews

Short flight so no entertainment, turbulence so no food service - overall flight as expected

8.0 ExcellentMichelle, Apr 2024NPL - AKL
Read more about Air New Zealand reviews

Short flight so no entertainment, turbulence so no food service - overall flight as expected

All was good, the only thing was it didn't run on time.

The staff and crew on board were excellent. Business class however, was very weird. I thought we would have individual pods, but the way it was set up was unexpected. Not very private and If you wanted to lay down, you had to have an entire bed made up for you by the crew, rather than how Delta one works where you could just lie down whenever you feel like it. It was a 16 hour flight. I chose not to have my bed made, and that turned out to be a good idea because everybody who had their bed made had to wait for the crew to roll up their mattresses. So strange!

Crew were pleasant, happy to be there and were a joy to be around. Entire operation was professional, well thought out and ran like a Swiss clock.

Couldn’t request a vegan meal somehow but I noticed other people getting them

United flight from SFO to PDX was cancelled. I will ask for a refund. Had to book on Alaska

Good food and entertainment options. Great Staff that were all welcoming and caregiving.

The recline on the seat in front of me came back so that I was staring at the top of the man’s head in front of me the whole trip. He refused to bring his seat back up twice every time he was instructed to do so and only relented when he had a tray of good in front of him. And then right back in my lap!!! Horrible man!! I complained to the staff multiple times, but no one would address the issue. Otherwise, it would have been a perfect flight.

Flight was canceled due to technical issue shortly before the check-in counters opened. Passengers were rebooked on a flight three days later. Request to be accommodated on Air Tahiti Nui could not be processed. Customer service sorted out the refund after calling and being put on hold for almost an hour.

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

All things were below standard. There were 2 crew on the flights but didn't ask for water. The flight connection was poor for 4 hours.

Flight delay was informed at the last minute. Food quality is not up to Qantas standard I was unable to book an online boarding pass on any of my 6 flights.

Following a marathon flight riddled by delays and changes from Santiago, Chile, my flight to Melbourne from Sydney was on schedule but I was transferred to the next flight. The reason by ticketing and the floor manager was I missed the entry to flight by one minute! That's right, the emphasised that if I was 1 minute earlier I would be on the flight. I asked what was the point them emphasising 1minute overdue and how that helped me or the situation. They didn't care at all. Replying that if it was one minute earlier they would've done something and smirking delivering the information. Australian's do call Australia home, Qantas calls Australian's suckers.

I was pleasantly surprised with my flight to LA with Qantas. Although seats were not the roomies, service was excellent.

Wonderful crew, good food. Absolutely loved the wine spritz and wish I could buy it!

Don’t like last minute airline change. Not able to choose seat earlier.

Enjoyed the new possibilities of in flight entertainment. Been awhile since I've flown, and that was a nice surprise. Being able to pick from such a variety was personalized and welcomed.

It's only a short trip from Sydney to Melbourne, which i have done many times. The trip met my expectations

I really appreciated the fact that when I checked my bags at the Quantas counter after arriving from an international flight an hour early, the agent noticed I had a very long layover. He then found an earlier flight that allowed me to get to Cairns several hours earlier than I planned. That was amazing because I had already traveled over 20 hours and wasn’t looking forward to such a long layover. It allowed me to see my daughter and grandchildren much earlier (it had been two years since I visited last).

Qantas cancelled my flight for no good reason and rebooked me into a middle seat.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Fresh fuit or veg snacks would be so great, but there are two good restaurants in Denver airport. Try Etais UDIS or Freshens DIA for nutritious delicious pita sandwiches/ donairs and crepes in Freshens.

Crowded plane but it flew on time and had friendly staff

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

The Air Canada agent was very helpful helping with my luggage and cat carrier when I went there instead of United.

United force you to download their App to do the check-in.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

Book Cheap Chicago Plane Tickets

Recent return flight deals

 
These are the cheapest return flights to Chicago found on KAYAK in the last 72 hours.
17/10Thu
2 stopsAmerican Airlines
38h 50mCHC-ORD
21/10Mon
2 stopsAmerican Airlines
39h 25mORD-CHC
$1,927
17/10Thu
2 stopsAmerican Airlines
40h 29mCHC-ORD
21/10Mon
2 stopsAmerican Airlines
32h 05mORD-CHC
$1,954
9/8Fri
2 stopsAir Canada
24h 46mAKL-ORD
18/8Sun
2 stopsAir Canada
32h 10mORD-AKL
$2,019
24/7Wed
3 stopsQantas Airways
55h 09mWLG-ORD
29/7Mon
2 stopsQantas Airways
28h 47mORD-WLG
$2,071
9/8Fri
2 stopsUnited Airlines
35h 25mAKL-ORD
18/8Sun
1 stopUnited Airlines
39h 15mORD-AKL
$2,075
24/8Sat
1 stopUnited Airlines
20h 00mAKL-ORD
14/9Sat
1 stopUnited Airlines
39h 55mORD-AKL
$2,080
10/9Tue
1 stopAir New Zealand
22h 58mAKL-ORD
15/9Sun
1 stopAir New Zealand
30h 30mORD-AKL
$2,134
17/10Thu
3 stopsQantas Airways
26h 08mCHC-ORD
21/10Mon
2 stopsQantas Airways
29h 50mORD-CHC
$2,854
20/6Thu
1 stopAir New Zealand
28h 00mAKL-ORD
20/7Sat
1 stopAir New Zealand
22h 50mORD-AKL
$2,891
27/6Thu
2 stopsAir Canada
30h 23mAKL-ORD
8/7Mon
3 stopsAir Canada
33h 05mORD-AKL
$12,998

Search by stops

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
18/9Wed
1 stopAir New Zealand
20h 43mAKL-ORD
$1,003
8/9Sun
2 stopsAir New Zealand
35h 07mWLG-ORD
$1,005
5/6Wed
2 stopsAir Canada
24h 54mAKL-ORD
$1,006
18/9Wed
2 stops
24h 51mAKL-ORD
$1,010
17/9Tue
1 stopAir New Zealand
22h 58mAKL-ORD
$1,011
12/5Sun
2 stopsDelta
22h 24mAKL-ORD
$1,023
12/5Sun
3 stops
33h 04mAKL-ORD
$1,040
12/5Sun
1 stopUnited Airlines
21h 32mAKL-ORD
$1,058
8/9Sun
3 stopsQantas Airways
36h 28mWLG-ORD
$1,070
5/6Wed
3 stopsAir Canada
53h 02mAKL-ORD
$1,161

Search by stops

Search by airline

Search by price

Recent domestic flight deals

17/9Tue
directSpirit Airlines
2h 39mLGA-ORD
17/9Tue
directSpirit Airlines
2h 11mORD-LGA
$150
14/5Tue
directSpirit Airlines
2h 39mLGA-ORD
15/5Wed
multi-stopSpirit Airlines
12h 22mORD-LGA
$185
14/5Tue
multi-stopSpirit Airlines
7h 54mLAX-ORD
15/5Wed
directSpirit Airlines
4h 31mORD-LAX
$193
26/5Sun
directDelta
2h 57mLGA-ORD
31/5Fri
directDelta
2h 15mORD-LGA
$197
26/5Sun
directDelta
2h 51mJFK-ORD
3/7Wed
directDelta
2h 30mORD-JFK
$205
12/6Wed
directJetBlue
2h 57mJFK-ORD
26/6Wed
directJetBlue
2h 25mORD-JFK
$213
29/5Wed
directJetBlue
2h 54mBOS-ORD
29/5Wed
directJetBlue
2h 26mORD-BOS
$213
22/5Wed
directUnited Airlines
2h 52mBOS-ORD
29/5Wed
directUnited Airlines
2h 35mORD-BOS
$234
22/5Wed
directUnited Airlines
2h 52mBOS-ORD
29/5Wed
multi-stopUnited Airlines
6h 15mORD-BOS
$282
14/5Tue
directAmerican Airlines
4h 08mLAX-ORD
16/5Thu
directAmerican Airlines
4h 27mORD-LAX
$386

Search by stops

Search by airline

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Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
2/5Thu
multi-stop
37h 35mAKL-ORD
14/5Tue
multi-stop
28h 25mORD-AKL
$21,810

Search by stops

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Flights to Chicago

Return flight deals:

Chicago - New Zealand

Cabin classes:

$10,967
$4,429
$1,966

Popular routes

The most searched flights to Chicago by KAYAK users.