$1,039 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 17/3. 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.
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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
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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 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.

Recent return flight deals to Chicago

Recommended return deals departing in the coming months from the most popular airlines that fly to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
23:30 - 06:42AKL-ORD
25h 12m2 stops
21:38 - 06:00ORD-AKL
39h 22m1 stop
$1,992
Find Deal
Thu, 3 Apr - Thu, 17 Apr
15:50 - 06:10AKL-ORD
31h 20m2 stops
15:35 - 10:25ORD-AKL
25h 50m2 stops
$2,026American Airlines
Find Deal
Tue, 1 Jul - Mon, 21 Jul
13:25 - 23:59AKL-ORD
27h 34m2 stops
17:36 - 14:00ORD-AKL
27h 24m2 stops
$2,088Qantas Airways
Find Deal
Wed, 21 May - Wed, 11 Jun
07:45 - 23:55AKL-ORD
33h 10m2 stops
09:12 - 22:55ORD-AKL
44h 43m2 stops
$2,098Qantas Airways
Find Deal
Thu, 19 Jun - Sun, 13 Jul
19:55 - 14:43AKL-ORD
35h 48m2 stops
13:01 - 15:05ORD-AKL
33h 04m3 stops
$2,324Air Canada
Find Deal
Thu, 29 May - Mon, 9 Jun
20:15 - 23:00AKL-ORD
19h 45m1 stop
16:40 - 06:00ORD-AKL
20h 20m1 stop
$2,398Air New Zealand
Find Deal
Wed, 21 May - Wed, 11 Jun
22:00 - 06:25AKL-ORD
25h 25m1 stop
14:25 - 06:00ORD-AKL
22h 35m1 stop
$2,502Air New Zealand
Find Deal
Wed, 30 Apr - Tue, 20 May
20:15 - 22:59AKL-ORD
19h 44m1 stop
06:00 - 06:00ORD-AKL
31h 00m1 stop
$2,587United Airlines
Find Deal
Tue, 1 Jul - Sun, 20 Jul
19:45 - 00:56AKL-ORD
22h 11m1 stop
07:10 - 06:00ORD-AKL
29h 50m1 stop
$2,594United Airlines
Find Deal
Tue, 1 Jul - Mon, 21 Jul
06:35 - 12:31CHC-ORD
47h 56m2 stops
14:05 - 23:05ORD-CHC
40h 00m3 stops
$2,875Air Canada
Find Deal
Wed, 2 Apr - Mon, 7 Apr

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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.
In the last 3 days, the cheapest flight deal to Chicago was found on the route from Christchurch, at $3,515 return. The most popular connection is from Auckland to Chicago and KAYAK users have found return deals for as low as $1,992 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip 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 Saturday where round-trip tickets can be as cheap as $2,048. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $2,512 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 February, where tickets cost $1,885 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 $2,478 and $2,462 respectively. For one-way flights, the best month to travel is February with an average price of $1,885.

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

The average price for all round-trip 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 afternoon, when round-trip flights cost $2,133 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 $2,492.

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 21 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 $288.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

High season

July

Cheapest flight

$1,039
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (5% 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

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Christchurch, at $3,515 return. The most popular connection is from Auckland to Chicago and KAYAK users have found return deals for as low as $1,992 in the last 3 days.

  • 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 $1,005. The cheapest price found on KAYAK in the last 2 weeks cost $942 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.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be March, April and May. The cheapest month to fly from New Zealand is February.
  • 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, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to New Zealand

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

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.
7.9
Air New ZealandOverall score based on 458 reviews
8.2Boarding
8.5Crew
7.4Entertainment
7.2Food
7.9Comfort
Airline reviews

Flew premium economy, well worth the extra. Much better seat size & space. Meals & snacks were lovely. Crew really pleasant. Internet is not great, not really useful for anything. Couldn't even send messages.

10.0 ExcellentMark, Feb 2025AKL - PER
Read more Air New Zealand reviews

Flew premium economy, well worth the extra. Much better seat size & space. Meals & snacks were lovely. Crew really pleasant. Internet is not great, not really useful for anything. Couldn't even send messages.

Everything was fine. Wish the wifi was free and included in the ticket price.

Nothing special short flight - all good - difference between 1 fudge and 2 fudge is obligation and thankfulness

The flight we had booked was cancelled due to bad weather conditions, but we were lucky to arrive at the airport quite early and got a seat on an earlier flight. The flight was mostly nice, but there were some hefty turbulences towards Queenstown. One of the passengers behaved hysterically. It would have been great if the crew had done something to calm her.

Sitting in an aisle seat equals getting hit by food cart and spilled on multiple times Food: gross and minimalistic Crew: frumpy and kurt Sound on multiple entertainment platforms poor Not an earplug problem, system soundboard poor

Major hassle with the weight of carryon luggage Having to repack bags at airport Not an issue in most of world Ridiculous issue considering the 400 pound gentleman sitting behind us

Overall experience was poor. In general crew was polite in speaking but that was all about it. I am vegetarian so I always carry a cup noodle box with me just in case. So I pressed "CALL" button for hot water for my cup noodle on my seat and waited for 10-15 minutes but nobody came. I personally took the box and went all the way to back of the plane. When I requested stewardess to put hot water in my cup noodle she refused as it was a "safety" hazard. I told her that you always serve coffee and tea these are also hot. But she still refused. I went back to my seat and from the seat I ordered hot water and it was brought to me without any problem. I poured THAT hot water in my cup noodle and ate. I was sitting in seat 36A, which was 2nd row in economy class. After eating my noodle I took the box and went 2 rows in the front where there was a kitchen to throw it. Again the stewardess there told me she didn't have a waste bin there and asked me to go back of the plane and throw it there. Tell me if above experiences are 'ok' for your airline??

Everything very good except the sofa couch not as comfortable as expected.

Liked the non-stop option, can always use more leg room!

Wonderful Airlines…our American Airlines could learn from ANZ. From boarding to landing everyone was professional and gracious. Kiwi’s really are the nicest of all people! Thank you

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.

I got upgraded from economy to business, and the experience was outstanding

I have taken this flight many times. It is ALWAYS late. Every time there is significant delay (1-3 hours) before boarding. It’s very consistent. Even after boarding the expected landing time was delayed twice. The seats are very narrow and cramped. Food is barely editable. Considering an economy ticket often costs about $2,000 it’s one of the worst services ever.

Boarding was over 3 hrs late and we didn’t land until almost 1:30am

American Airlines was their usual junk service — but at least it got us down to LA. I was more irritated that while they codeshare with Alaska Airlines in Seattle, they could not out our flight on one of these, opting for one of the small SkyWest operated American Eagle flights — and causing a 14 hour layover. Which I accepted due to a $2000 difference in airfare — that said it was irritating for a flight that usually would have cost around $100 extra, if that.

nothing to complain about w/the food, and professionalism of the crew. i just cant stand being on a flight for that long of a time.

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)

Good communication regarding any updates time of flight and flight delayed. The fight was delayed by two and half hours at eleventh hour. That was unexpected, especially when you international passenger.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

The only issues I have are the seats are very small and so is the overhead storage. You should mention that while booking flights. I had plenty of knee room but I am wider than my seat, and I am not fat at all. The Mitsubishi 900 models need to be upgraded to western size people. I do not know how a 300 pound woman fit into those seats. I had to continuously lean away from the aisle to keep people and flight crew from bumping into my shoulder. 3 hour flight so no entertainment or food, just snacks and a drink, which was no big deal. The buttery/garlic pretzels were pretty tasty.

If you want your flight to get delayed constantly for 13+ hours and given a 10 dollar food voucher the. I would say take air canada. Worst experience ever.

My flight was cancelled and I was left to figure out where to find a hotel, something to eat and how to get a new flight at 11:30pm. Wasted a day. Thanks, Air Canada!

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

They kept changing the gate (6 times in 30 minutes) and then left us on the plane for 4 hours before departure. Likely was the storm, which is understandable, but the lack of communication and the e constant running between gates at opposite ends of the airport really threw me and my friend for a loop.

Legitimately everything about this flight was awful, was also so delayed I never want to use air Canada again

Terrible all around. Flight was late and airplane was very uncomfortable. The crew were unhelpful and hid in the back. Did zero work. No entertainment.

Because I am quite tall a bit more leg room would have been more comfortable. Out of three seats I had the middle one, unfortunately.

I like the free beer and wine but not the delays to the departure time.

Never again flying economy on Rouge!!! Literally like sardines!!! Will try to change to better seats 3 seat arrangement only so so if traveling with family. Who wants to squished to stranger!!😖 Can’t say enough bad about this!!!

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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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