Cheap Flights to Chicago

View NZ$166 flight on Sat, 15 Nov 2025Opens in a new window

Popular airlines to Chicago

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Cheap Tickets to Chicago

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 28 Oct - Sat, 1 Nov
LAX
Los Angeles
ORD
Chicago
NZ$332 Return, found 6 days ago
NZ$332
Return
found 6 days ago
Select Delta flight, departing Tue, 28 Oct from Los Angeles to Chicago, returning Sat, 1 Nov, priced at NZ$332 found 6 days ago
Hawaiian Airlines
Sat, 1 Nov - Sun, 2 Nov
LAX
Los Angeles
ORD
Chicago
NZ$355 Return, found 6 days ago
NZ$355
Return
found 6 days ago
Select Hawaiian Airlines flight, departing Sat, 1 Nov from Los Angeles to Chicago, returning Sun, 2 Nov, priced at NZ$355 found 6 days ago
American Airlines
Thu, 23 Oct - Sat, 25 Oct
LAX
Los Angeles
ORD
Chicago
NZ$360 Return, found 1 hour ago
NZ$360
Return
found 1 hour ago
Select American Airlines flight, departing Thu, 23 Oct from Los Angeles to Chicago, returning Sat, 25 Oct, priced at NZ$360 found 1 hour ago
United
Wed, 21 Jan - Tue, 3 Feb
AKL
Auckland
ORD
Chicago
NZ$1,406 Return, just found
NZ$1,406
Return
just found
Select United flight, departing Wed, 21 Jan from Auckland to Chicago, returning Tue, 3 Feb, priced at NZ$1,406 just found
Qantas Airways
Sat, 31 Jan - Sun, 22 Feb
AKL
Auckland
ORD
Chicago
NZ$1,436 Return, found 2 hours ago
NZ$1,436
Return
found 2 hours ago
Select Qantas Airways flight, departing Sat, 31 Jan from Auckland to Chicago, returning Sun, 22 Feb, priced at NZ$1,436 found 2 hours ago

Chicago Flights

Although this city is filled with all of the usual hustle and bustle, it still manages to maintain its laid-back, Midwestern American charm.
Travellers gather to this destination to soak up some culture at the Chicago Cultural Centre, see the water show at the Buckingham Fountain, or get a view of the city from the Hancock Observatory.
Food enthusiasts delight in a plethora of dining options downtown, while nature lovers enjoy the Grant Park Rose Gardens. With no shortage of things to do, tourists abound in this city. Despite this, cheap flights to Chicago are easy to find most of the year.

Best time to go to Chicago

Peak Season:

Flights to Chicago are at their most expensive from June through September. Although it’s humid, the temperature is warm and beautiful, making it a great time to discover Lake Michigan, or stroll through Humboldt Park.

Shoulder Season:

April and May, and October to December make up the shoulder season in Chicago. Crowds thin out during these cooler months, so this is a fantastic time to either take the Hop On Hop Off city tour, visit the Museum of Science and Industry, or peacefully wander through the Navy Pier.

Off Season:

Due to the bitter weather from January through March, flights are inexpensive and tourists are few. Although it can be chilly, this is one of the best times to indulge in one of the many indoor activities, like seeing a performance at The Second City comedy theatre or the Lyric Opera, dancing at Enclave, or exploring the Shedd Aquarium.

Chicago Airport and transfer information

Chicago O'Hare International Airport (ORD)
Distance: 27km northwest of city centre
Offering door-to-door service at a reasonable price, the Go Airport Express shuttle bus is one of the most convenient methods of ground transport. Alternatively, you can take a taxi or a public bus. Both take around 25 - 90 minutes to arrive at your destination.
Taxis can be expensive, but are one of the more flexible options. Buses buses are inexpensive, but are sometimes delayed. Car rentals are also available at a higher price.

Online resources for your travel to Chicago

http://www.safetravel.govt.nz/destinations/unitedstates.shtmlOpens in a new window
The Safetravel website provides details on travel safety, as well as information on entry requirements and important local contacts.
http://www.flychicago.com/About/OHare/Default.aspxOpens in a new window
The Chicago O'Hare International Airport website offers details on flights, services, and ground transport.

Frequently asked questions

What is the name of Chicago's airport?
Chicago has more than one airport, but most travellers touch down at O'Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Chicago?
The journey from O'Hare Intl. Airport (ORD) to downtown Chicago is fairly long. You'll need to travel 26 kilometres before you can check in to your city hotel.
What airport is best to fly into Chicago?
A flight to Chicago means hopping off the plane at O'Hare Airport or Chicago Airport. The first is 26 kilometres away from downtown. The second is 14 kilometres away.
How many airlines fly to Chicago?
There are a total of 51 airlines connecting Chicago with 237 airports globally.
Which airlines fly to Chicago?
Chicago receives the highest number of flights from United Airlines, American Airlines and Delta with United Airlines being the number one choice of airline. New York is the most popular city for passengers to jet off from.
How many nonstop flights are there to Chicago?
With roughly 7 564 nonstop flights running every week, you'll be hitting the runway in Chicago before you can ask, "Are we there yet?"
Where are the most popular flights to Chicago departing from?
The most popular flights to Chicago set off from New York, Washington and Dallas airports.
How long is the flight to Chicago Airport?
If it's New York you're leaving behind, you'll be in the air for around 2 hours and 44 minutes before you arrive in Chicago. Terminal to terminal from Washington generally takes 2 hours and 15 minutes and from Dallas, the average flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Chicago?
Don't leave booking your flight to Chicago until the last minute. That's one trick seasoned travellers use to get the best prices. Booking well in advance means more choices and cheaper flights. Don't stop there, however. Do some research and see if there is more than one airport at your destination. Fares often differ depending on which airport you go for. Don't forget to compare fares across air carriers too. Finally, another easy way to save a few dollars is be ready to book at a moment's notice. If you stumble on a good bargain, don't hold off — grab it while you can.
Do you have any tips for my flight to Chicago?
Depending on where you're coming from, your trip to Chicago could be simple and straightforward or it could go on forever. We've put together some handy tips that will help you start your next unforgettable escape on the right foot. What to pack in your hand luggage:

  • It's simple — first, pack your passport, travel documents, wallet and daily medications. Next, you'll need some in-flight entertainment to while away the hours. A thrilling book and a laptop filled with your favourite shows are some wonderful options. If you intend to take a quick nap, a neck pillow and a pair of earplugs will also be useful. Finally, leave some space for a few toiletry items to ensure you touchdown feeling fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of shampoo and hair gel in your checked luggage. Any gels or liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp or pointed objects, like a Swiss Army knife, and dangerous products which are explosive or flammable, such as spray paint, flares and fireworks, are also restricted.

What to wear on a flight:

  • Choose comfort over style. Prepare for changes in temperature by donning layers, and opt for flat, enclosed shoes like sneakers.
  • Most of us have heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To reduce your risk on board, stay hydrated, consider wearing compression socks and move your lower limbs often.

How to get through airport security fast when flying to Chicago?
The secret is to be well prepared before you arrive at airport security. That way, you'll be boarding that plane to Chicago in a flash. Follow these helpful tips and get your holiday off to a fantastic start:

  • First things first. Your passport and boarding pass will need to be shown to airport security personnel. Keep them at hand so you don't have to dig around for them.
  • Your belt, jacket, keys and other small items, like your headphones, will need to go through the X-ray machine. Make the whole process faster by removing them as your turn draws near.
  • For just a few moments, you'll need to unplug from the digital world. Your phone, laptop and any other electronic gadgets will need to go through the scanner.
  • Remove all gels and liquids from your hand luggage. They often need to be sent through the X-ray machine separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a single quart-size (one litre), clear zip-close bag.
  • The right choice of footwear can save you several minutes. Boots are often required to be removed and X-rayed separately. Slip-on shoes usually aren't.
  • Airlines will not allow any sharp objects to come on board with you. If you must bring these kinds of items, check them in.

Flights to Chicago information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
NZ$248

Trending flights to Chicago

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, 21 Jan - Tue, 3 Feb
AKL
Auckland
ORD
Chicago
NZ$1,406 Return, just found
NZ$1,406
Return
just found
Select United flight, departing Wed, 21 Jan from Auckland to Chicago, returning Tue, 3 Feb, priced at NZ$1,406 just found
*Available to Expedia members.