$787 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 21/2. 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, 0 bags

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
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Everything you should know

Cheapest return fare
$1,280
Overall average: $2,153
Air Canada
Wed 18/3Tue 7/4
AKL - ORD • 2 stops
Cheapest one-way flight
$694
Typical prices: $962-$1,088
Air Canada
Sat 21/2
AKL - ORD • 2 stops
When to travel
February
Cheapest • 22% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Wed, 18 Mar - Tue, 7 Apr
Air Canada Logo
06:15 - 14:41
AKL
-
ORD
26h 26m2 stops
Air Canada Logo
15:40 - 00:30
ORD
-
AKL
39h 50m2 stops
$1,280Air Canada
Wed, 18 Mar - Tue, 7 Apr
Multiple Airlines Logo
06:15 - 14:41
AKL
-
ORD
26h 26m2 stops
Multiple Airlines Logo
14:00 - 14:10
ORD
-
AKL
31h 10m3 stops
$1,388Multiple Airlines
Tue, 3 Feb - Tue, 24 Feb
American Airlines Logo
15:50 - 06:01
AKL
-
ORD
33h 11m1 stop
American Airlines Logo
16:49 - 09:10
ORD
-
AKL
21h 21m1 stop
$1,490American Airlines
Thu, 12 Feb - Mon, 16 Feb
American Airlines Logo
06:05 - 05:55
WLG
-
ORD
42h 50m2 stops
American Airlines Logo
16:49 - 13:35
ORD
-
WLG
25h 46m2 stops
$1,513American Airlines
Thu, 12 Feb - Mon, 16 Feb
American Airlines Logo
06:05 - 05:55
WLG
-
ORD
42h 50m2 stops
American Airlines Logo
10:49 - 13:35
ORD
-
WLG
31h 46m2 stops
$1,515American Airlines
Thu, 12 Feb - Mon, 16 Feb
American Airlines Logo
06:05 - 07:25
CHC
-
ORD
44h 20m2 stops
American Airlines Logo
13:15 - 13:15
ORD
-
CHC
29h 00m2 stops
$1,549American Airlines
Thu, 12 Feb - Mon, 16 Feb
American Airlines Logo
06:05 - 12:31
CHC
-
ORD
49h 26m2 stops
American Airlines Logo
13:15 - 13:15
ORD
-
CHC
29h 00m2 stops
$1,551American Airlines
Tue, 3 Feb - Tue, 24 Feb
Air Canada Logo
06:15 - 14:41
AKL
-
ORD
27h 26m2 stops
Air Canada Logo
15:35 - 19:00
ORD
-
AKL
32h 25m2 stops
$1,565Air Canada
Tue, 3 Feb - Tue, 24 Feb
Air Canada Logo
07:00 - 14:41
AKL
-
ORD
26h 41m2 stops
Air Canada Logo
13:12 - 16:50
ORD
-
AKL
32h 38m3 stops
$1,578Air Canada
Thu, 19 Feb - Thu, 26 Feb
Air New Zealand Logo
17:15 - 23:04
WLG
-
ORD
24h 49m2 stops
Air New Zealand Logo
18:17 - 16:10
ORD
-
WLG
26h 53m2 stops
$2,055Air New Zealand
Booking Insights

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 $1,608 on average for one-way flights. On the other hand, the most expensive months are April and July, where the average cost of tickets from New Zealand is $2,471 and $2,412 respectively. For return trips, the best month to travel is February with an average price of $1,608.

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, with an average flight price of $342.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight$694
Best time to beat the crowds (10% less expensive on average)
Most popular time to fly and prices are also 14% 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $2,252. On the other hand, the most expensive day to fly is Sunday, where prices are $2,339 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 at night, when flights cost $2,252 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 $2,252.

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, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 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, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Reviews of the 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.
8.0
Fiji AirwaysOverall score based on 216 reviews
7.5Entertainment
7.5Food
8.5Crew
8.0Comfort
8.1Boarding
Airline reviews

We have had an absolutely horrific experience so far getting home from Australia on a $18,000 + flight we booked with you. The flight did not deplane in Dallas because there was no available gate or staircase. We sat in the plane for 3 hours waiting to deplane. As a result we missed our connecting flight to New York. American Airlines put us up in a hotel several miles away. We waited 45 minutes for a shuttle and The shuttle driver was horribly rude and unhelpful. They offered us $70 vouchers for food but actually there was no food left when we arrived minus some chicken nuggets and corn dogs. It was awful. Horrible way to end a vacation. There has to be accountability here.

2.0 MediocreAnonymous, Jan 2026
NAN - DFW
Read more Fiji Airways reviews

We have had an absolutely horrific experience so far getting home from Australia on a $18,000 + flight we booked with you. The flight did not deplane in Dallas because there was no available gate or staircase. We sat in the plane for 3 hours waiting to deplane. As a result we missed our connecting flight to New York. American Airlines put us up in a hotel several miles away. We waited 45 minutes for a shuttle and The shuttle driver was horribly rude and unhelpful. They offered us $70 vouchers for food but actually there was no food left when we arrived minus some chicken nuggets and corn dogs. It was awful. Horrible way to end a vacation. There has to be accountability here.

A bit cramped in economy and the people in front wouldn’t put their seats up during meal service, crew did not help with that and I felt they could have done more about it.

The airline is ok, but it needs to improve it schedules.

Again, Fijian hospitality was genuine, very comfortable, only improvement would be the entertainment. Why Do they only have 5 episodes of TV shows and from like season three...

Fiji Airways was amazing, will definately be lfying them again. The "Fijian hospitality" is not a catch phrase, it is genuine. the only things that could be improved is the entertainment. Not a great choice of movies, and the TV shows only have about 5 or so episodes, and often of a random season.

They will look to squeeze every penny they can out of you!! Pick your seat$$...bring luggage$$$$... if they could charge you for the air on the plane they would!!

.very good and as I needed wheelchair assistance all staff excellent.. only suggestion is get rid of those plastic chairs hard to ride in and staff have trouble compared to others. Everything else very good experience. Will use Fiji Air again.

In-flight entertainment options could use a refresh, Consider a tie-up with Spotify for more current music and with IMDB or other service for newer selections/movie ratings.

See previous comments. Didn’t take this flight because my other flight was so delayed. Ending up on two other flights as a result and was more than a day late.

6 hour delay and they didnt try to make up any time during an over 10 hour flight

The disembarking steps in Wellington were precarious and I felt quite insecure. There was no one on the tarmac to greet us and help. The embarking ramp in Blenheim was much more satisfactory. The rest of the flight was fine.

Air conditioning was turned to the wrong setting. Way too hot. The entertainment system kept resetting and didn’t work half the flight. Said something to the crew. They didn’t do anything to help. Plane had a mechanical problem that resulted in 2.5 hour delay. Boarded the plane, had to disembark and get back on.

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.

Good and appreciate the effort Air Zealand puts into using more environmentally friendly food containers and utensils. yay! One of the better airlines for this for sure. Still some bad stuff, but at least Air NZ is trying. :) Also really enjoyed the bluetooth option for personal headsets. :)

I was trying to get confirmation on if my luggage was going to be moved to the earlier flight (I requested standby to get home earlier) and was unable to get help from those working at the counter. The request to be moved to an earlier flight was handled smoothly through the app and appreciate the ease of the request.

They are my favourite airline in the world by a million miles.

Do the bumpy weather the whole trip they were very few times when the seatbelt sign wasn't on

Great except paying $240 usd for 2 pounds over on a checked luggage. Outrageous.

Kayak did not propagate my United miles account and I had to manually get credit.

Like: Aircraft was better than others I've flown in. Crew was great, food was very good. Air New Zealand is now my favorite airline. On our long flight from AKL to YVR there was enough room for those of us in Economy to stretch a bit. My sister is disabled and they took very good care of her and me. Best entertainment offering of all the other airlines. Not so much; Flight from AKL to YRV was delayed BUT they recovered really well so no complaints here. Pretty petty point to complain about. Only negative I have. I will recommend to friends.

After already paying for excess luggage prior to flight, i was advised AT check in that i had to pay $816 or forfeit my flight! The lady at the counter was SO rude and had already started offboarding me when i said i would pay it after asking her three times for the exact amount! Have lodged a formal complaint yet heard nothing. Will not ever travel via Qantas again

Basic airline, aircraft and service. AA gets you from point A to B. My flight was delayed by 2 hours too.

No internet on flight, which makes log travels really hard.

My flight from Dallas to Sydney was cancelled. My entire trip was rerouted to include the following: Hartford to Washington DC Washington DC to JFK JFK to Auckland Auckland to Christchurch I paid for an aisle seat on the flight to Auckland and was asked if I would take a window seat to accommodate a family. The agent at the podium failed to mention that the family had a 3 month old baby and that a bassinet would be used during the 16 hour flight. The only way I could get out of my seat was to crawl under the bassinet of the sleeping baby. I think it is wrong that I was no given the choice to sit in another seat, that the agent knew what she was doing and chose to not properly disclose my seating arrangement. Terrible treatment.

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.

We were upgraded and after just a short delay in attending to a safety check we were on our way. Would definately fly Qantas International on their Dreamliner again.

I tried to check in online but was unable to do so. I stood in line for nearly two hours to check in. American Airlines was understaffed. When I finally got to the kiosk to check in, I was still unable to check in. No AA staff was available to help. Finally one of the airport security agents who was helping passengers became of lack of AA Staff told me: “I think the reason you can’t check in is that you are starting your name with an upper case letter when you write it. Just write it with all lower case letters.” That did allow me to check in. HOW COULD ANYONE POSSIBLY KNOW THAT IF THEY USE AN INITIAL UPPER CASE LETTER TO SPELL THEIR OWN NAME, AA WOULD NOT ALLOW THEM TO CHECK IN?????? Then I had to wait in line over half an hour again to drop off my baggage. Although I arrived at the airport 3 hours early, by the time I got to the gate, they had already started boarding.

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

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.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

They are very proactive and made our boarding easy and always notified us about any changes well in advance.

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

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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.