Cheap Flights to Chicago

Airlines that fly to Chicago

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 35% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at AU$739 for one-way flights and AU$1,167 for return, for the period specified. Prices and availability are subject to change. Additional terms apply.
Qantas Airways
Sydney — Chicago
SYD - ORD with Qantas Airways
Mon, 17 Mar
Qantas Airways
Chicago — Sydney
ORD - SYD with Qantas Airways
Wed, 26 Mar
Found 1 day ago
From AU$1,167
Select flight from Sydney to Chicago, departing on March 17 with Qantas Airways, and returning from Chicago to Sydney on March 26 with Qantas Airways. Price from AU$1,167, Found 1 day ago.
EVA Airways
Brisbane — Chicago
BNE - ORD with EVA Airways
Mon, 10 Feb
EVA Airways
Chicago — Brisbane
ORD - BNE with EVA Airways
Tue, 25 Feb
Found 21 hours ago
From AU$1,625
Select flight from Brisbane to Chicago, departing on February 10 with EVA Airways, and returning from Chicago to Brisbane on February 25 with EVA Airways. Price from AU$1,625, Found 21 hours ago.
Air Canada
Brisbane — Chicago
BNE - ORD with Air Canada
Mon, 10 Feb
Air Canada
Chicago — Brisbane
ORD - BNE with Air Canada
Tue, 25 Feb
Found 21 hours ago
From AU$1,925
Select flight from Brisbane to Chicago, departing on February 10 with Air Canada, and returning from Chicago to Brisbane on February 25 with Air Canada. Price from AU$1,925, Found 21 hours ago.
Korean Air
Sydney — Chicago
SYD - ORD with Korean Air
Mon, 3 Nov
Korean Air
Chicago — Sydney
ORD - SYD with Korean Air
Mon, 10 Nov
Found 1 day ago
From AU$1,956
Select flight from Sydney to Chicago, departing on November 3 with Korean Air, and returning from Chicago to Sydney on November 10 with Korean Air. Price from AU$1,956, Found 1 day ago.
Japan Airlines
Sydney — Chicago
SYD - ORD with Japan Airlines
Thu, 23 Oct
Japan Airlines
Chicago — Sydney
ORD - SYD with Japan Airlines
Mon, 3 Nov
Just found
From AU$2,022
Select flight from Sydney to Chicago, departing on October 23 with Japan Airlines, and returning from Chicago to Sydney on November 3 with Japan Airlines. Price from AU$2,022, Just found.

Chicago Flights

A city of extremes, Chicago mingles sophisticated theatres with gritty jazz clubs, massive concrete structures with small patches of lush greenery, mild pastimes with a wild nightlife. Cheap flights to Chicago are relatively easy to find during the majority of the year, which is important, as you will want to spend your money on the city's vast dining menu, cultural sites, and fantastic accommodations.

Best time to go to Chicago

Peak Season:

The months of June through September make up the peak season in Chicago. Despite the high humidity, flights to Chicago tend to be pricey during this period, as visitors crowd the streets to enjoy the warmth, play on the lakefront, or go sightseeing on one of the many local tours.

Shoulder Season:

The shoulder season in Chicago falls in April and May, then again in October to December. The climate ranges from warm and pleasant, to crisp and cool. Although many visitors prefer to avoid the chill, these months are still great as the city sees vibrant flora during spring, romantic reds and oranges during autumn and clean, glimmering snow at the start of winter.

Off Season:

From January through March, Chicago sees its bitterest weather. Although many tourists flee the area in search of warmer climates, this is still a good time to go as you will be able to enjoy the New Years celebrations, take advantage of inexpensive flights and explore the city in solitude.

Chicago Airport and transfer information

Chicago O'Hare International Airport (ORD)

Distance: 27km northwest of city centre

The Go Airport Express shuttle bus is one of the most convenient methods of ground transport. This shuttle offers door-to-door service, is reasonably-priced, and relatively quick. Taxis and public buses are two other convenient methods. Both take around 25 minutes to an hour and half to arrive, depending upon your destination; however, taxis allow for more flexibility, but can be expensive, while the bus system is inexpensive, but is prone to delays. Alternatively, you can rent a car at a slightly higher rate.

Online resources for your travel to Chicago

The Chicago O'Hare International Airport website gives information on flights, transport, and available services. The Smartraveller website offers tips on travelling to America, such as entry and exit requirements, security issues, and important local contacts.

Top Flight Routes from Chicago

Top Flight Routes to Chicago (ORD)

Travel beyond your imagination, book your Chicago holidays (hotel+flight) with Expedia and save more!

Frequently asked questions

What is the name of Chicago's airport?
Chicago has more than one airport, but most travellers fly into O’Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Chicago?
ORD is 26 kilometres from downtown Chicago, so be prepared for a bit of a journey into the city.
What airport is best to fly into Chicago?
If you’re jumping on a plane to Chicago, you’ll most likely land at O’Hare Intl. Airport (ORD) (26 kilometres from downtown). Midway Intl. Airport (MDW) (14 kilometres from downtown) is the other major airport here.
How many airlines fly to Chicago?
Chicago is serviced by 45 air carriers from at least 220 worldwide airports.
Which airlines fly to Chicago?
In general, travellers fly with American Airlines, United Airlines and Delta Air Lines when going to Chicago. The largest number of these flights come in from Queens Village, with American Airlines flying this route the most frequently.
How many nonstop flights are there to Chicago?
Arranging an unforgettable Chicago getaway is a cinch when there are 8 014 nonstop flights each week to pick from.
Where are the most popular flights to Chicago departing from?
Travellers frequently depart from Atlanta, Denver and Dallas airports when heading to Chicago.
How long is the flight to Chicago Airport?
If you’re flying to Chicago from Queens Village, you’re looking at a flight duration of 2 hours and 34 minutes. Those leaving from Washington can expect to be travelling for 2 hours and 5 minutes. From Denver it’s approximately 2 hours and 23 minutes away.
How to book the cheapest flight to Chicago?
Don’t leave locking in your flight to Chicago until the very last minute. That’s one move well-versed travellers use to get the best deals. Booking in advance means more options and cheaper flights. Don’t stop there, though. Do some research and see if there is more than one airport at your destination. Ticket prices often differ depending on which airport you pick. Make sure you compare fares across airlines too. And finally, remember that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to book your ticket as soon as you see a great bargain. The best deals never last long.
How to survive the flight to Chicago?
If you’re not prepared, airports and flying can be testing. But don’t hit the panic button just yet. Follow these useful tips and enjoy a trouble-free start to your getaway in Chicago.What to pack in your hand luggage:

  • It’s simple — first, pack in your passport, important documents, cash and daily medications. Next, you’ll want some entertainment to while away the time. A thrilling novel and a laptop crammed with your favourite movies are some fantastic options. If you intend to take a short snooze, a quality neck pillow and a pair of noise-cancelling headphones will also come in handy. Finally, make room for a toothbrush and some facial wipes to ensure you arrive at your destination looking fresh and raring to go.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between airlines, the general guide to follow is nothing flammable, sharp or explosive. This includes knives, scissors, spray paint and flares. Sporting equipment like bows and arrows, and objects that could harm passengers, such as pepper spray and firearms, can’t come on board with you either.

What to wear on a flight:

  • Your number one priority is to be as comfortable as possible. Layer up with loose, breathable clothing and remember to bring a pullover in case it gets cool in the cabin. Pick a pair of well-fitting, flat shoes as it’s possible that your feet and ankles will swell a little during the journey. Leave the high heels and hiking boots in your checked baggage.
  • The serious condition by the name of DVT (deep vein thrombosis) is a potential risk on long-haul flights. It’s the result of blood clots forming due to poor circulation. Walking up and down the aisle and doing leg and foot exercises while seated is a great way to prevent this from happening. Wearing a quality pair of compression socks or tights is also recommended.

How to get through airport security fast when flying to Chicago?
A little pre-planning before your flight can make your getaway to Chicago easy and painless. Check out our handy tips and tricks for a stress-free journey past security:

  • First things first. Your passport and travel documents will need to be shown to security personnel. Keep them within easy reach to avoid fumbling around for them.
  • Time to strip down. Well kind of. Your jacket, belt, keys and other contents of your pockets, like your headphones, will need to go on a tray through the X-ray machine. Make the whole process faster by removing them as it gets closer to your turn.
  • All your electronic devices, including your tablet and phone, are also required to be separately scanned.
  • Remember to remove gels and liquids from your hand luggage. They often need to be sent through the X-ray separately. Each product should be no larger than 3.4 ounces (100 milliliters) and everything must fit inside a quart-size (one litre), clear zip-lock bag.
  • Lightweight sneakers are a clever footwear choice as you’re less likely to be asked to remove them when passing through security. Safety boots and other heavy shoes are often subjected to additional screening.
  • Sharp or pointed objects (like knives and scissors) can’t be taken on board. They’ll be confiscated at security, so pack them safely away in your checked bags.

Flights to Chicago information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Return price
AU$215

Trending flights to Chicago

Prices were available within the past 7 days and start at AU$739 for one-way flights and AU$1,167 for return, for the period specified. Prices and availability are subject to change. Additional terms apply.
*Available to Expedia members.