Cheap Flights from Sydney (SYD) to Chicago (CHIA)

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Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Sydney Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Sydney Airport to Chicago? If you want to travel next month, return fares start from £808. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Sydney to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Sydney to Chicago flights are currently cheapest in August.

Sydney to Chicago: Flight information

The things to know before you go.
Cheapest flight found£341
Cheapest month to flyAugust

Finding cheap flights from Sydney to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Sydney to Chicago is £808. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Sydney to Chicago. But we found flights with one or more stops from £808.
As of April 2026, there are no flights flying from Sydney to Chicago.
The cheapest month to fly from Sydney to Chicago is usually May.
If you're flying from Sydney Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the centre of Chicago. We've found flights into this airport from £808.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sydney Airport to Chicago on Monday, 18 May 2026.
No airlines currently offer direct flights between Sydney Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Fiji Airways offers the cheapest flight tickets to Chicago.

Flying from Sydney Kingsford Smith International Airport (SYD) to Chicago: what you need to know

  • The timezone in Chicago is UTC-6. The city is 17 hours behind Sydney, where Sydney Kingsford Smith International Airport is located.

  • To avoid missing your SYD to Chicago flight, leave enough time to check in and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • Be prepared for longer queues in popular months like July. Arriving up to four hours ahead of international flights and two hours for domestic departures will give you plenty of time for security and boarding.

  • Consider adding a stopover to potentially land a cheaper plane ticket from SYD to Chicago. Just deselect 'Direct flights only' during your search. Give yourself a breather (and maybe even a better deal) by stopping at one of these airports:

    • Dallas Fort Worth International Airport (DFW)

    • Los Angeles International Airport (LAX)

    • San Francisco International Airport (SFO)

  • Travelling from central Sydney to SYD takes about 15 minutes by public transport. If you drive, ride-share or take a taxi, you'll cover the 8 kms (5 miles) in 20 minutes or so, depending on traffic.

  • Catching an early flight from Sydney Kingsford Smith International Airport to Chicago? Avoid rushing to the airport (and catch some extra z's) by choosing one of these hotels close to SYD:

  • When it comes to Sydney Kingsford Smith International Airport's on-time performance, data shows 66% of flights arrive within the expected time frame.

How to find the cheapest flights from Sydney Kingsford Smith International Airport (SYD) to Chicago

  • The lowest price we've seen for a one-way Sydney Kingsford Smith International Airport to Chicago flight is £341. The cheapest price for a return flight is £808. Keep in mind fares can change due to availability at the time of booking.

  • To find cheap flights from SYD to Chicago, book early. Airlines generally offer lower fares when flights first go on sale.

  • Scoring cheap tickets from Sydney Kingsford Smith International Airport to Chicago is more likely if you can be flexible with your travel plans. Try using the 'Whole month' search tool to get the best prices across every month and walk away with a fantastic deal.

  • Save time searching for cheap flights from SYD to Chicago by setting up a Price Alert. We'll send you an email or notification through the app when a special offer becomes available.

  • Pick your preferred arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Sydney Kingsford Smith International Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kms (17 miles) from central Chicago. If you're getting a taxi or a ride-share, the drive takes about 30 minutes.

  • It'll take around 45 minutes if you're travelling on public transport.

  • Look into staying at a hotel close to ORD if you have a late flight from Sydney Kingsford Smith International Airport to Chicago. Pick one of these options and make your first night all about rest:

  • To lock in the lowest price, reserve your vehicle from Chicago O'Hare International Airport about four weeks in advance of your flight from SYD to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Sydney Kingsford Smith International Airport to Chicago has hit the runway, you can make your way to the city centre in about 25 minutes by car. Central Chicago is roughly 16 kms (10 miles) from Chicago Midway International Airport (MDW).

  • If you're catching public transport, it'll take around 30 minutes.

  • After stepping off your SYD to Chicago flight, kick back at a hotel close to MDW. These are some great options that'll help you sink into relaxation mode:

  • Score the best price by reserving your ride from MDW four weeks in advance. You'll also have access to a wider selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Sydney Kingsford Smith International Airport to Chicago and make your way to your hotel or start sightseeing right away. Central Chicago is around 145 kms (90 miles) from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to drive there.

  • The journey will take roughly 2 hours when travelling by public transport.

  • Enjoy a more leisurely start to your break by staying at a hotel near RFD after your SYD to Chicago flight. Unwind after a day of travel or just give yourself time to get your bearings in a new destination at:

  • If you prefer a particular make or model, booking early gives you a better shot at snagging what you want. Reserve your ride from RFD at least a few weeks ahead of your flight from Sydney Kingsford Smith International Airport to Chicago.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • It's time to figure out your trip dates for your flight from Sydney Kingsford Smith International Airport to Chicago. July is the busiest month for a trip to Chicago. If you prefer a more low-key vibe, go in January.

  • Book a Sydney Kingsford Smith International Airport to Chicago plane ticket with a departure in July if you're eager to visit the city during its warmest month. You can expect temperatures to range from 16ºC to 28ºC.

  • Look for cheap tickets from SYD to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the perfect place to stay. After booking your flight from Sydney Kingsford Smith International Airport to Chicago, check out our selection of accommodation options including:

  • There are so many things to explore in this city it can be hard to figure out where to start. Art Institute of Chicago, Millennium Park and Willis Tower are top attractions which should be on any good Chicago itinerary.

Explore more of the United States

  • Chicago is easy to fall in love with, but there are so many other corners of the United States just waiting to be explored. About 451 kms (280 miles) southeast of Chicago, a visit to Columbus will keep you on the move. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Indianapolis is another standout destination in the United States and is around 257 kms (160 miles) southeast of Chicago. No journey is complete without dropping by Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.