$710 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 8/9. 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
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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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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Mon, 6 Oct - Tue, 18 Nov
American Airlines Logo
15:50 - 05:34AKL-ORD
31h 44m2 stops
American Airlines Logo
11:00 - 10:25ORD-AKL
28h 25m2 stops
$1,230American Airlines
Find Deal
Wed, 10 Sep - Wed, 17 Sep
American Airlines Logo
15:50 - 05:31AKL-ORD
30h 41m2 stops
American Airlines Logo
15:06 - 10:25ORD-AKL
26h 19m2 stops
$1,236American Airlines
Find Deal
Thu, 16 Oct - Sun, 19 Oct
Air Canada Logo
06:50 - 15:00AKL-ORD
26h 10m2 stops
Air Canada Logo
15:45 - 14:55ORD-AKL
29h 10m2 stops
$1,416Air Canada
Find Deal
Mon, 15 Sep - Mon, 29 Sep
 Logo
14:10 - 22:43AKL-ORD
25h 33m2 stops
 Logo
06:30 - 13:40ORD-AKL
37h 10m2 stops
$1,443
Find Deal
Mon, 15 Sep - Mon, 29 Sep
 Logo
14:10 - 22:43AKL-ORD
25h 33m2 stops
 Logo
06:30 - 13:40ORD-AKL
37h 10m2 stops
$1,447
Find Deal
Thu, 2 Oct - Fri, 28 Nov
Air Canada Logo
06:50 - 16:42AKL-ORD
27h 52m2 stops
Air Canada Logo
15:40 - 17:20ORD-AKL
30h 40m2 stops
$1,479Air Canada
Find Deal
Thu, 2 Oct - Tue, 14 Oct
Qantas Airways Logo
07:10 - 17:56AKL-ORD
28h 46m2 stops
Qantas Airways Logo
15:14 - 14:05ORD-AKL
28h 51m2 stops
$1,505Qantas Airways
Find Deal
Fri, 28 Nov - Fri, 5 Dec
Qantas Airways Logo
06:05 - 15:52CHC-ORD
28h 47m2 stops
Qantas Airways Logo
14:15 - 15:25ORD-CHC
30h 10m2 stops
$1,566Qantas Airways
Find Deal
Thu, 2 Oct - Wed, 15 Oct
Air New Zealand Logo
14:50 - 23:12AKL-ORD
26h 22m1 stop
Air New Zealand Logo
06:00 - 05:30ORD-AKL
29h 30m1 stop
$1,596Air New Zealand
Find Deal
Fri, 26 Sep - Fri, 31 Oct
Air New Zealand Logo
20:15 - 23:15AKL-ORD
20h 00m1 stop
Air New Zealand Logo
18:25 - 08:10ORD-AKL
19h 45m1 stop
$1,598Air New Zealand
Find Deal
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 $1,564 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 $2,476 and $2,350 respectively. For one-way flights, the best month to travel is February with an average price of $1,564.

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 $333.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight$710
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly and prices are also 11% 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 Saturday where round-trip tickets can be as cheap as $1,953. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $2,278 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, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, +79 more

ANA, Aer Lingus, +80 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, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, +79 more

ANA, Aer Lingus, +80 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
Air New ZealandOverall score based on 504 reviews
8.2Boarding
8.0Comfort
7.4Entertainment
7.3Food
8.5Crew
Airline reviews

Not a comfortable trip, the seats are not good, and they look old.

4.0 OkayAnonymous, Jul 2025AKL - SFO
Read more Air New Zealand reviews

Not a comfortable trip, the seats are not good, and they look old.

Lost my luggage and brought someone else luggage to my airport.

Not entirely positive. It’s frustrating that everything is done through the united app. One of our flight attendants on our trip from San Francisco to MSP continually had trouble hearing people so she flipped her hair into people’s faces

I flew United from San Francisco to Auckland. My connecting flight from Auckland to Christchurch was canceled with no explanation. I was finally told the cancellation was due to fog. Even though it was clear when we landed. I am from San Francisco, I know what fog is! And I didn't see any fog. I was told the next available flight was 7 hours later. Unacceptable, they should have had a flight ready to go as soon as it was deemed safe to take off.

Our original flight was cancelled from SFO to AKL on 6/16/25. So we had to stay overnight at a hotel after a 12-hour layover plus 3-hour delay before the cancellation. Then had to fly to LA and then to AKL the following day losing an entire day of our vacation in NZ, that we can never get back.

Two hours was not enough time to transition from the international to domestic terminal. You have to go through customs, a biological hazard check, gather your luggage, take a bus to the domestic terminal and recheck your luggage. The bus was slow and crowded and the lines to recheck your bags were very long. We missed our connecting flight. Initially, the Air New Zealand officials were not helpful at all in helping to get us on another flight. Told us we would have to buy another ticket for a flight 11 hours later. Found another agent that was more helpful. He helped arrange to get us on standby for another flight three hours later. Had to ride in jump seats next to the flight attendants, but at least we eventually got to out destination.

Full flight. Flight attendants were harried. Otherwise, fine for the typical cramped seating conditions in coach.

Great! Flight was delayed by 30 mins but all was great. Thanks.

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.

Great as usual, some delays but well communicated and made up for in the air

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.

Business class points redemption - good value for points paid, dubious value if out of your own pocket, domestic class business product okay for this length of flight. The flight left and arrived on time, crew were good, aircraft was a bit old and tired, but still miles ahead of their competitors in Virgin and Jetstar.

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.

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

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Horrible, experience, 5 hours delay, they changed gates 3 times, the last one we had to wait for 1::30 hre for the door to open to get to that gate. 0 apologies from Air Canada, they don’t care at all about their passengers

I paid for comfort plus seats but did not get the extra leg room. When I told the stewardess, she just ignored me.

Great breakfast and coffee …..fastest bag service I have ever had in NOLA

I had a very disappointing experience with customer service. I was suffering from a severe viral infection that included a rash and persistent cough, leaving me unable to even sit upright. Given the circumstances, I requested travel credits from Canada Air, explaining the potential health risk to others onboard. However, the airline showed no concern for my condition and stated they were not in a position to make decisions based on health considerations. Despite my illness, I received no support or flexibility. Ultimately, I chose to forgo my flight due to their lack of responsiveness. It’s unfortunate that airlines like this operate without prioritizing passenger health and safety.

Late departing. Late arriving. More worried about limiting bags on board. Free beer and wine a nice surprise.

I did not noticed baggage was separate - I had assumed international flights included luggage, so it surprised me I had to pay to check a bag.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

My return flight experience was one of the worst times I have had traveling anywhere this year. Not because of the flight. It was because there was not enough time allocated to deplane, go through U.S. Customs and U.S. Security to get to the gate for the connecting flight to Boston which I missed, There was well less than an hour between my landing in Montreal from Prince Edward Island to my connecting gate. I even called Air Canada on the morning of my return and noted my concern over the short layover time, not more that 45 minutes. The initial flight was four minutes late. I was seated in the rear of the first aircraft, and it took at least 20 minutes to deplane. The U.S. Customs was a considerable distance from the gate at which we landed. The need for double security seemed unnecessary and redundant. The distance from the security to my gate was again fairly great, and the wrong gate number was listed on my boarding pass. The agent I approached at the flight that was going to Newark, New Jersey was too busy to answer my question as to what gate was for Boston. When I got to the right gate, they had just closed the door to the aircraft even though I arrived a minute late. If I knew the distance to Customs and from Security to the gate, I would have asked for a seat on the next available flight which was 4:30 pm. When I made my call at 6:00AM that morning. When I asked the agent at the Boston gate, he said that the 4:30 flight was already “OVERBOOKED!” I was put on an 8:30 PM flight and didn’t get home until MIDNIGHT. I then had to care for a barnful of hungry animals and didn’t get to bed until 2:00 AM.

From Montreal to Cincinnati the flight was perfect! Flight free and everyone was perfect and a pleasure to travel with. But from Casablanca to Montreal the flight crew were quite cold, unhelpful, also seemed to scold many passengers instead of simply educating or instructing them. There were a couple for sure I could describe but not name… i was really shocked bc my experience w air Canada is typically a good one at the very least. It seemed something was very much so I’m the air w the crew. The two older lady crew members and the male were amazing but the younger lady crew members w the exception of one were very clique-y and snarky, sassy

Seating wasn’t too cramped; I don’t understand how luggage bins get full if there are enough for each person. Shouldn’t there be room for the designated carry-on and personal item for each passenger at their seat? THEN, IF for some reason extra room is available for someone who prefers it, then shifts can occur. I’m simply saying it seems that I should have primary access to the storage bin at my seat and underneath in front of me. It was suggested that I go to the back of the plane to store my carry-on when I paid to have access to the first seat after 1st class. The additional stress and inconvenience could be avoided and I think all passengers and flight crew are interested in guidelines that are fair, clear, and reduce tension.

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