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Cheap Flights from Sydney to Chicago Midway

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Compare Sydney to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from Sydney to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Sydney to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.Rs165,504 per passenger.Departing Sat, 31 May.One-way flight with Qantas.Outbound indirect flight with Qantas, departs from Sydney on Sat, 31 May, arriving in Chicago Midway.Price includes taxes and charges.From Rs165,504, select.
Chicago.Rs185,033 per passenger.Departing Fri, 25 Apr.One-way flight with Qantas.Outbound indirect flight with Qantas, departs from Sydney on Fri, 25 Apr, arriving in Chicago Midway.Price includes taxes and charges.From Rs185,033, select.
Chicago.Rs221,023 per passenger.Departing Mon, 31 Mar.One-way flight with Jetstar.Outbound indirect flight with Jetstar, departs from Sydney on Mon, 31 Mar, arriving in Chicago Midway.Price includes taxes and charges.From Rs221,023, select.
Chicago.Rs426,511 per passenger.Departing Mon, 30 Jun.One-way flight with Qantas.Outbound indirect flight with Qantas, departs from Sydney on Mon, 30 Jun, arriving in Chicago Midway.Price includes taxes and charges.From Rs426,511, select.
Chicago.Rs829,502 per passenger.Departing Wed, 2 Jul.One-way flight with Korean Air.Outbound indirect flight with Korean Air, departs from Sydney on Wed, 2 Jul, arriving in Chicago Midway.Price includes taxes and charges.From Rs829,502, select.
Chicago.Rs831,999 per passenger.Departing Thu, 30 Oct.One-way flight with Korean Air.Outbound indirect flight with Korean Air, departs from Sydney on Thu, 30 Oct, arriving in Chicago Midway.Price includes taxes and charges.From Rs831,999, select.
Chicago.Rs831,999 per passenger.Departing Tue, 19 Aug.One-way flight with Korean Air.Outbound indirect flight with Korean Air, departs from Sydney on Tue, 19 Aug, arriving in Chicago Midway.Price includes taxes and charges.From Rs831,999, select.
Chicago.Rs831,999 per passenger.Departing Wed, 3 Sep.One-way flight with Korean Air.Outbound indirect flight with Korean Air, departs from Sydney on Wed, 3 Sep, arriving in Chicago Midway.Price includes taxes and charges.From Rs831,999, select.

Find the cheapest month to fly from Sydney to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Sydney to Chicago Midway flights are currently cheapest in May.
Mar
from Rs221,023
Apr
from Rs185,033
May
from Rs165,504
Jun
from Rs426,511
Jul
from Rs829,502
Aug
from Rs831,999
Sep
from Rs831,999
Oct
from Rs831,999
Nov
from Rs831,999
Dec
from Rs837,763
Jan
from Rs915,388
Feb
Find prices

Sydney to Chicago Midway: Alternative routes

Compare routes from Sydney to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Sydney to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs165,504
Cheapest month to flyMay

Finding cheap flights from Sydney to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Sydney to Chicago Midway is Rs559,865. 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 Midway. But we found flights with one or more stops from Rs559,865.
As of March 2025, there are no flights flying from Sydney to Chicago Midway.
The cheapest month to fly from Sydney to Chicago Midway is usually March 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sydney Airport to Chicago Midway Airport on Tuesday, 1 April 2025.
No airlines currently offer direct flights between Sydney Airport and Chicago Midway Airport. 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 Midway 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.
Currently, Qantas offers the cheapest flight tickets to Chicago Midway.

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

  • Travelling during a peak time like a bank holiday? Expect longer queues at security and check-in. Give yourself extra leeway and arrive up to four hours before international flights and two hours ahead of domestic departures.

  • We make it a breeze to book a flight with a stopover. To see all your options for flights from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, pick a flight offering a stop long enough to explore your chosen city. Some popular stopovers between SYD and MDW are:

    • Los Angeles International Airport

    • Dallas/Fort Worth International Airport

    • San Francisco International Airport

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

  • The lowest price we've found for a one-way ticket from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport is Rs165,504. For a return flight on this route, the best price is Rs559,865. Depending on the availability and when you book, these fares may change.

  • To pick up cheap flights from SYD to MDW, book as early as possible. Airlines tend to offer lower prices when flights are first released.

  • Getting cheap flights from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport is easier if you're flexible with your travel dates. Use the 'Whole month' function to see the lowest prices across every month and bag a great deal.

  • Set up a Price Alert for cheap flights from SYD to MDW. You don't need to check every day to find out if fares have fallen. We'll tell you as soon as the price changes.

  • Use filters to find the right trip for you. To see the 'Best,' 'Fastest' or 'Cheapest' flights from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport, use the 'Sort by' tool. You can also filter results by airline, departure and arrival times, and number of stops.

Handy information about Sydney (Kingsford Smith) Airport (SYD)

  • Sydney (Kingsford Smith) Airport is around 18 kilometres from central Sydney. If you're driving, catching a cab or ride-sharing from the centre, it'll take you 21 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the trip time to be around 27 minutes.

  • Booked an early flight from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport? Avoid the hassle of rushing to the airport (and sneak in some extra snooze time) by choosing one of these stays near SYD:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 21 minutes to get to the centre driving.

  • It'll take around 46 minutes if you're travelling on public transport.

When to fly to Chicago Midway International Airport (MDW)

  • The quietest month for a flight from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport is May, while July is the most popular. Choose the ideal time to visit Chicago based on whether you prefer a bustling atmosphere or a more laid-back vibe.

  • Before locking in your flight from Sydney (Kingsford Smith) Airport to Chicago Midway International Airport, think about the type of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Look for cheap flights from SYD to MDW around that time if you want to travel in cooler conditions.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • After you've secured your cheap ticket to Chicago Midway International Airport, explore the lowest prices and exclusive offers on hotels. You can also compare a range of car rental companies in one place to find the best car rental price for your Chicago trip.

Plan the rest of your trip from Sydney to Chicago

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