$1,037 Find Cheap Flights to Chicago – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest return flight
$1,821
Typical prices: $2,093-$2,744
Qantas Airways
Fri 16/3Mon 26/3
CHC - ORD • 2 stops
Cheapest one-way flight
$891
Typical prices: $1,112-$1,543
Multiple Airlines
Thu 1/3
AKL - ORD • 2 stops
Top airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
Top routes
Cheapest • 13% average savings
Most popular
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
+1
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 enjoy your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Tue, 16 Mar - Fri, 26 Mar
Qantas Airways Logo
06:00 - 19:45CHC  Christchurch-ORD Chicago O'Hare Intl
31h 45m2 stops Sydney Kingsford Smith Los Angeles
Qantas Airways Logo
13:37 - 15:25ORD  Chicago O'Hare Intl-CHC Christchurch
31h 48m2 stops San Francisco Sydney Kingsford Smith
$1,821Qantas Airways
Sat, 30 Jan - Tue, 16 Feb
Qantas Airways Logo
13:20 - 19:59AKL  Auckland Intl-ORD Chicago O'Hare Intl
25h 39m1 stop Dallas/Fort Worth
Qantas Airways Logo
13:23 - 09:55ORD  Chicago O'Hare Intl-AKL Auckland Intl
25h 32m1 stop Los Angeles
$1,853Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
American Airlines Logo
09:40 - 05:03WLG  Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
American Airlines Logo
17:59 - 17:20ORD  Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,860American Airlines
Thu, 25 Feb - Mon, 1 Mar
American Airlines Logo
09:40 - 05:03WLG  Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
American Airlines Logo
17:59 - 17:20ORD  Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,871American Airlines
Sat, 30 Jan - Tue, 16 Feb
Qantas Airways Logo
07:30 - 16:54AKL  Auckland Intl-ORD Chicago O'Hare Intl
28h 24m2 stops Sydney Kingsford Smith Los Angeles
Qantas Airways Logo
12:11 - 09:55ORD  Chicago O'Hare Intl-AKL Auckland Intl
26h 44m1 stop Los Angeles
$1,871Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
American Airlines Logo
09:40 - 05:03WLG  Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
American Airlines Logo
17:59 - 17:20ORD  Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,874American Airlines
Sat, 30 Jan - Tue, 16 Feb
Qantas Airways Logo
06:50 - 14:12AKL  Auckland Intl-ORD Chicago O'Hare Intl
26h 22m2 stops Brisbane Dallas/Fort Worth
Qantas Airways Logo
16:54 - 18:00ORD  Chicago O'Hare Intl-AKL Auckland Intl
30h 06m2 stops Dallas/Fort Worth Sydney Kingsford Smith
$1,890Qantas Airways
Thu, 25 Feb - Mon, 1 Mar
American Airlines Logo
09:40 - 05:03WLG  Wellington-ORD Chicago O'Hare Intl
38h 23m2 stops Auckland Intl Los Angeles
American Airlines Logo
17:59 - 17:20ORD  Chicago O'Hare Intl-WLG Wellington
28h 21m2 stops Dallas/Fort Worth Auckland Intl
$1,896American Airlines
Tue, 16 Mar - Fri, 26 Mar
Air New Zealand Logo
13:15 - 18:50CHC  Christchurch-ORD Chicago O'Hare Intl
23h 35m1 stop San Francisco
Air New Zealand Logo
14:15 - 09:25ORD  Chicago O'Hare Intl-CHC Christchurch
25h 10m2 stops Houston George Bush Intcntl Auckland Intl
$2,308Air New Zealand
Thu, 10 Dec - Thu, 24 Dec
Air New Zealand Logo
15:50 - 19:05AKL  Auckland Intl-ORD Chicago O'Hare Intl
22h 15m1 stop San Francisco
Air New Zealand Logo
05:30 - 05:45ORD  Chicago O'Hare Intl-AKL Auckland Intl
29h 15m1 stop Houston George Bush Intcntl
$2,404Air New Zealand
Booking Insights

Price, demand, and travel trends for flights to Chicago

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What is the cheapest flight to Chicago?

Christchurch to Chicago is the cheapest route at $1,821 return, found in the past 5 days on KAYAK. Auckland to Chicago is the most popular connection with return deals from $1,853.

How much is a flight to Chicago?

On average, a return flight from New Zealand to Chicago costs $2,391, based on KAYAK data over the past 12 months. Return fares from Wellington average $2,161, while Auckland runs a bit higher at $2,385.

What is the cheapest day to fly to Chicago?

Saturday is the cheapest day to fly to Chicago at $2,223 return on average over the past 12 months on KAYAK. Friday is the most expensive at $2,602.

What is the cheapest month to fly to Chicago?

•February is the cheapest month to fly to Chicago with an average price of $1,839 return.
•May ($2,818) and June ($2,625) are the most expensive.

Based on KAYAK data over the past 12 months.

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

Night flights to Chicago are the cheapest at $2,000 return on average. Evening flights are the most expensive at $2,489.

What is a good deal for flights to Chicago?

Flights under $2,093 are considered a good deal. 25% of KAYAK users found return flights to Chicago at or below these prices, with the lowest fares from:
•Auckland $2,048
•Wellington $2,073.

Key details for flights to Chicago

Low season

March

Cheapest flight

$891
Beat the crowds with an average 72% drop in travellers.
The most popular month to fly with an average 65% increase in travellers.
One-way flight from Auckland to Chicago O'Hare Intl Airport

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

Your questions about flights to Chicago, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Chicago is a good deal?

    A good deal on a flight to Chicago is around $2,093 return. This fare is in the lowest 25% of return flight prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • Which airports serve Chicago?

    Flights to Chicago arrive at: Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • What is the difference between the most popular and the most frequent airline at Chicago?

    American Airlines operates the most flights from New Zealand to Chicago at 0 per week, while Air New Zealand is the airline most often selected by KAYAK users searching for flights from New Zealand to Chicago. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80.5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

Your guide to booking Chicago flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For flights to Chicago, a good return fare is around $2,093. If you find a fare below that, you're getting a strong deal.
  • If your travel dates are flexible, consider flying to Chicago in February. Return fares historically average $1,839, making February the cheapest month to travel based on KAYAK data from the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to evening to save up to $489 on a return flight. Evening flights to Chicago average $2,000 compared to $2,489 for afternoon flights.
  • Once you arrive in Chicago, a great place to start is River North. It is popular with first-time visitors and can give you a good feel for the area.

Reviews of the top 3 airlines flying to Chicago

 
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 679 reviews
7.4Food
7.4Entertainment
8.5Crew
8.2Boarding
7.9Comfort
Airline reviews

Premium economy seats and food we're very nice although the price could be more affordable so we can do it more often.

10.0 ExcellentSharon, Sept 2026
Read more Air New Zealand reviews

Premium economy seats and food we're very nice although the price could be more affordable so we can do it more often.

mechanical issue, so delayed take-off (hence the low boarding rating) and made a number of people miss their connecting flight. Also took a long time to get our checked baggage. I luckily made mine with 5 minutes to spare, but it was nerve-racking.

The flight was smooth and on time. Entertainment options were lacking and there was no food, other than some very boring snacks.

A better selection of entertainment would have been nice. I found nothing that appealed to me as a middle-aged traveler. The flight attendants were gracious, helpful, and attentive. It also would have been nice to have more bathrooms as the flight was full and the plane was big.

The Premium Economy seats were very comfortable and the food was quite tasty. I did not use the entertainment system, but I was able to charge my phone and tablet with the seatback connection.

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!

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

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.

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

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

Overall, it was a very good experience. I would have given it a 10/10, especially based on our flight from SFO to Melbourne. The cabin crew on that flight were wonderful and incredibly attentive. They took extra care when setting up our beds so we could sleep comfortably without being disturbed. Dinner was served promptly and smoothly. I woke up quite late, when the flight was already preparing for landing, and the crew still made sure I was taken care of. They brought me English tea in a proper cup, and when it was time to prepare the cabin for landing, they thoughtfully transferred it into a takeaway cup so I could continue enjoying it along with some breakfast. Those small, thoughtful gestures made the long flight feel much more comfortable and special. The service from the SFO to Melbourne crew was truly excellent.

Having the computer outage compounded by delayed takeoff while waiting for aircrew (who were also delayed) resulted in me missing my int’l flight

We had a cancellation due to weather, but the American Airlines staff was very helpful. Once we got on a plane, the trip was great.

Great food and good entertainment options for the long flight.

Loved the food and beverages available, spacious economy class, excellent entertainment

We booked with Qantas instead of Delta and we instead flew on American Airlines. American is not our favorite to go on. No leg room and the width of seats are a joke. Your are packed like sardines on American flights.

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.

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)

Overall a positive experience. As long as you are not connecting-I found the discount offered by Kayak and the customer service to be very good.

I had bad experience with United airline. No live rep, they only have AI that respond to customers concern

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

Travelling to a place near Chicago?

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

More options for your flight to Chicago