$758 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 28/4. 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest return fare
$1,224
Typical prices: $1,586-$1,992
American Airlines
Mon 23/2Wed 4/3
AKL - ORD • 1 stop
Cheapest one-way flight
$758
Typical prices: $1,123-$1,674
Multiple Airlines
Tue 28/4
AKL - ORD • 2 stops
When to travel
November
Cheapest • 24% 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

Mon, 23 Feb - Wed, 4 Mar
American Airlines Logo
15:50 - 16:37
AKL
-
ORD
43h 47m
1 stop
American Airlines Logo
16:49 - 09:10
ORD
-
AKL
21h 21m
1 stop
$1,224American Airlines
Tue, 28 Apr - Tue, 5 May
Multiple Airlines Logo
20:15 - 05:50
AKL
-
ORD
26h 35m
1 stop
Multiple Airlines Logo
06:20 - 12:40
ORD
-
AKL
37h 20m
2 stops
$1,446Multiple Airlines
Thu, 11 Jun - Mon, 6 Jul
Qantas Airways Logo
13:25 - 23:59
AKL
-
ORD
27h 34m
2 stops
Qantas Airways Logo
19:00 - 14:05
ORD
-
AKL
26h 05m
2 stops
$1,674Qantas Airways
Mon, 23 Feb - Wed, 4 Mar
United Airlines Logo
15:50 - 21:36
AKL
-
ORD
24h 46m
1 stop
United Airlines Logo
12:35 - 09:10
ORD
-
AKL
25h 35m
2 stops
$1,752United Airlines
Fri, 27 Mar - Sun, 24 May
Air New Zealand Logo
13:15 - 00:59
CHC
-
ORD
29h 44m
1 stop
Air New Zealand Logo
14:40 - 09:35
ORD
-
CHC
25h 55m
2 stops
$1,930Air New Zealand
Wed, 25 Mar - Wed, 1 Apr
Qantas Airways Logo
06:05 - 20:40
CHC
-
ORD
32h 35m
2 stops
Qantas Airways Logo
16:44 - 14:45
ORD
-
CHC
28h 01m
2 stops
$2,053Qantas Airways
Fri, 27 Mar - Fri, 3 Apr
Air New Zealand Logo
13:15 - 00:59
CHC
-
ORD
29h 44m
1 stop
Air New Zealand Logo
21:20 - 11:25
ORD
-
CHC
44h 05m
2 stops
$2,084Air New Zealand
Tue, 10 Mar - Tue, 17 Mar
Air Canada Logo
09:55 - 14:41
WLG
-
ORD
22h 46m
2 stops
Air Canada Logo
13:12 - 00:05
ORD
-
WLG
40h 53m
3 stops
$2,084Air Canada
Fri, 27 Mar - Sun, 24 May
United Airlines Logo
13:15 - 22:55
CHC
-
ORD
27h 40m
2 stops
United Airlines Logo
08:51 - 09:35
ORD
-
CHC
31h 44m
2 stops
$2,198United Airlines
Fri, 27 Mar - Fri, 3 Apr
Air Canada Logo
06:10 - 19:45
CHC
-
ORD
31h 35m
3 stops
Air Canada Logo
15:40 - 00:05
ORD
-
CHC
38h 25m
2 stops
$3,004Air Canada
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 March, where tickets cost $1,528 on average for one-way flights. On the other hand, the most expensive months are April and December, where the average cost of tickets from New Zealand is $2,736 and $2,311 respectively. For return trips, the best month to travel is November with an average price of $1,497.

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 $328.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight$758
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 10% 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 $2,157. On the other hand, the most expensive day to fly is Sunday, where prices are $2,240 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 $2,157 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 $2,157.

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.

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 225 reviews
8.0Comfort
7.5Entertainment
7.5Food
8.5Crew
8.1Boarding
Airline reviews

Ticketing said dinner for the almost 14 hour flight and we were delayed an hour. However, onboard we were only served a sluce if pizza bread and a cookie. Not at all dinner and insufficient for a long international flight. Breakfast was good.

8.0 ExcellentAnonymous, Jan 2026
DFW - NAN
Read more Fiji Airways reviews

Ticketing said dinner for the almost 14 hour flight and we were delayed an hour. However, onboard we were only served a sluce if pizza bread and a cookie. Not at all dinner and insufficient for a long international flight. Breakfast was good.

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.

Space between seats on Air New Zealand is generally tight. The crew on this flight was excellent! Very attentive and nice. You get free wine or beer and chips and of course the Air New Zealand candies. 1 hour and 35 min flight approximately.

Your entertainment could be better. I flew on Air New Zealand in January so was expecting a better choice in February...but no luck. Same choices and also could have a better selection. Otherwise, lovely service, the purser came to our seats to welcome us. Overall, very nice. Direct flight from Auckland to YVR was fantastic!

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!

Very quick flight so no time for refreshments. We took off. Then landed. The end. Seats were too tight. Very cramped Grateful for the short flight cos moving around wasn’t possible

Please add more Bollywood movies and recent movies to the entertainment.

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.

Flight arrived late with no one to help over 30 people rebook. I slept at the airport.

Business seats not as comfortable or private as most competitors (e.g. Qantas was outstanding), and movie selection was much more limited than Qantas or United has been recently

I'd like to see AA's flight safety record clearly and prominently posted online.

Hard to move and get out of my seat when the passenger in front is in recline position.

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.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

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.

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

Better entertainment & food options more may be adding chicken option or on vegetarian side good quality pasta

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

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond
Benton Harbor
New Buffalo

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.