$550 Find Cheap Flights to Chicago – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 15% 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 fare
$1,404
Typical prices: $1,383-$1,705
Multiple Airlines
Mon 19/10Mon 26/10
SYD - ORD • 3 stops
Cheapest one-way flight
$550
Typical prices: $1,225-$1,407
Multiple Airlines
Tue 20/10
SYD - ORD • 2 stops
Top routes
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 11% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
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 love 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

Mon, 19 Oct - Mon, 26 Oct
Multiple Airlines Logo
14:15 - 05:16SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
31h 01m3 stops Nadi Los Angeles Las Vegas Harry Reid Intl
Multiple Airlines Logo
06:30 - 12:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
38h 05m3 stops Denver Intl Los Angeles Nadi
$1,404Multiple Airlines
Fri, 4 Dec - Sat, 5 Dec
Qantas Airways Logo
21:25 - 05:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 34m1 stop San Francisco
Qantas Airways Logo
21:00 - 06:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
40h 25m1 stop Los Angeles
$1,460Qantas Airways
Mon, 19 Oct - Sun, 1 Nov
Cathay Pacific Logo
12:20 - 13:55BNE  Brisbane-ORD Chicago O'Hare Intl
40h 35m1 stop Hong Kong Intl
Cathay Pacific Logo
14:10 - 10:45ORD  Chicago O'Hare Intl-BNE Brisbane
28h 35m1 stop Hong Kong Intl
$1,567Cathay Pacific
Fri, 16 Oct - Fri, 23 Oct
Multiple Airlines Logo
14:20 - 05:16MEL  Melbourne-ORD Chicago O'Hare Intl
30h 56m3 stops Nadi Los Angeles Las Vegas Harry Reid Intl
Multiple Airlines Logo
06:20 - 12:25ORD  Chicago O'Hare Intl-MEL Melbourne
38h 05m3 stops Dallas/Fort Worth Los Angeles Nadi
$1,574Multiple Airlines
Wed, 21 Oct - Thu, 29 Oct
Cathay Pacific Logo
12:20 - 13:55BNE  Brisbane-ORD Chicago O'Hare Intl
40h 35m1 stop Hong Kong Intl
Cathay Pacific Logo
15:10 - 23:20ORD  Chicago O'Hare Intl-BNE Brisbane
41h 10m1 stop Hong Kong Intl
$1,614Cathay Pacific
Wed, 4 Nov - Mon, 9 Nov
Air New Zealand Logo
11:50 - 21:45SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
26h 55m2 stops Auckland Intl San Francisco
Air New Zealand Logo
09:15 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 20m2 stops Houston George Bush Intcntl Auckland Intl
$1,751Air New Zealand
Tue, 3 Nov - Wed, 11 Nov
Air New Zealand Logo
07:30 - 20:35SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 05m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
14:00 - 10:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
27h 35m2 stops Los Angeles Auckland Intl
$1,772Air New Zealand
Wed, 4 Nov - Mon, 9 Nov
American Airlines Logo
20:30 - 10:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 35m2 stops Honolulu Dallas/Fort Worth
American Airlines Logo
06:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
33h 31m1 stop Los Angeles
$1,830American Airlines
Wed, 4 Nov - Mon, 9 Nov
American Airlines Logo
20:30 - 10:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 35m2 stops Honolulu Dallas/Fort Worth
American Airlines Logo
06:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
33h 31m1 stop Los Angeles
$1,839American Airlines
Mon, 12 Oct - Mon, 26 Oct
Qantas Airways Logo
13:00 - 18:35SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 35m1 stop Dallas/Fort Worth
Qantas Airways Logo
08:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
32h 31m1 stop Los Angeles
$1,895Qantas Airways
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends into flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Sydney, at $1,404 return. The most popular connection is from Melbourne to Chicago, while KAYAK users have found return deals for as low as $1,574 in the last 5 days.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is May, where tickets cost $1,560 on average for return flights. On the other hand, the most expensive months are July and December, where the average cost of tickets from Australia is $1,914 and $1,901 respectively. For one-way flights, the best month to travel is February with an average price of $1,106.

How far in advance should I book a flight to Chicago?

To get a below average price, you should book around 2 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport (MDW), with an average flight price of $313.

Good to know – Book Cheap Chicago Plane Tickets

Low season

March

Cheapest flight

$550
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Sydney to Chicago O'Hare 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

FAQs - booking Chicago flights

  • What is mobility assistance like at Chicago O’Hare Airport?

    There are wheelchair accessible shuttle buses that can take you between the terminals as well as accessible restrooms. In Terminal 2, there is a special Changing Places Facility that features a roll-in shower, a lift system and other accessible features like wall mounts and automatic doors.

  • Are there hotels on site at Chicago Midway Airport?

    Although there are no on-site hotels at Chicago Midway Airport, there are quite a few hotels that are only a short drive away. Both Holiday Inn Express & Suites Chicago-Midway Airport and Hampton Inn Chicago-Midway Airport are only a few minutes away and can be reached by a free airport shuttle.

  • Are there lounge options at Chicago O’Hare Airport?

    For those waiting on a layover, Chicago O’Hare Airport features lounges at all the domestic terminals (1, 2 and 3) and the international terminal (5). Some lounges (like Delta Sky Club in Terminal 2) are for members only, but others (like United Club in Terminal 1 and 2) offer day passes for purchase. Each lounge offers a quiet place to relax or get some work done with workstations, beverages, snacks and comfortable seating.

  • Does Chicago O’Hare International Airport provide facilities for families?

    Entertaining energetic children at Chicago O’Hare International Airport is easy thanks to a big aviation-themed play area and the ‘The Kid On The Fly’ exhibition. The airport features mother’s rooms where moms can nurse and change their babies; there are also changing stations located throughout the airport building.

  • Are there hotels near Chicago O’Hare International Airport?

    The Hilton Chicago O’Hare Airport Hotel is located in the airport grounds and connects to the domestic terminal buildings, making it a convenient idea for those who want to get to their boarding gates in no time at all. Aloft Chicago O’Hare is located near the airport and offers free airport transfers that run every half an hour from 5am until midnight. There is also the Sheraton Chicago O’Hare with a free round-the-clock airport shuttle for guests.

  • Does Chicago Midway Airport offer free Wi-Fi?

    You can access the Internet for free at Chicago Midway International Airport, but only for 30 minutes. Those who have to spend more time at Chicago Midway Airport and need a connection for longer can purchase a premium service.

  • How do I get to the city centre from Chicago Midway International Airport?

    Similarly to O’Hare Airport, Chicago Midway International Airport is well connected with the public buses that stop all over the city. If you are pressed for time, opt for the CTA Orange Train, which will get you to the centre of Chicago in about 20 minutes.

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Sydney, at $1,404 return. The most popular connection is from Melbourne to Chicago, while KAYAK users have found return deals for as low as $1,574 in the last 5 days.

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (14 km). You'll travel 26 km to reach the center of Chicago if you land in Chicago O'Hare Airport and 126 km if you land in Chicago Greater Rockford.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
  • There is a chapel available in Terminal 2 (Mezzanine Level) if you’d like a moment of quiet contemplation and prayer at Chicago O’Hare Airport (ORD). It provides a quiet place along with material for worship.
  • If you need to exchange your Australian dollars (AUD) for US dollars (USD) at Chicago O’Hare Airport, there are currency exchange services in Terminals 1, 2, 3 and 5. There are plenty of ATMs as well. If you’re at Chicago Midway Airport (MDW), there is a foreign currency exchange in Concourse A.
  • If you’re hungry while at Chicago Midway Airport, there are dining options available in Concourses A and B as well as Central Market. Food ranges from coffee and a bagel to fast food chicken to fish and chips. Most of the 24-hour options are in the Central Market area.
  • When booking flights to Chicago, you might notice that the Chicago area is served by more than one airport. The main airports are Chicago O’Hare International Airport, which is also the biggest and the busiest, and Midway International Airport, which is smaller but closer to central Chicago. Chicago Rockford International Airport, in the northern part of Illinois, is the furthest away from Chicago and mostly functions as a cargo airport.
  • Those who want to stretch and get rid of any stress after a long flight to Chicago have yoga rooms at their disposal at both Chicago O’Hare International and Chicago Midway airports. People who prefer something more active while at Chicago O’Hare International Airport can access the Hilton Athletic Club for a fee and make use of the gym or swimming pool.
  • Art enthusiasts will surely appreciate Chicago O’Hare International Airport’s art exhibitions, with artworks including sculptures and paintings displayed around the airport. Make sure to see the neon tunnel called ‘The Sky is the Limit’, which is the airport’s highlight piece.
  • For a fast trip from Chicago O’Hare International Airport to the city centre you can take the CTA Blue Line Train, operating 24 hours a day. Those who have a lot of luggage can choose the Go Airport Express shuttle, which will drop them off in front of their hotel.
  • If you have to charge the battery on your phone after your flight to Chicago, Midway Airport boasts ‘Get Plugged In’ charging points located around the airport. The stations include a comfortable seat where you can rest while bringing your phone back to life.

Reviews of the top 5 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 668 reviews
7.9Comfort
7.4Entertainment
8.2Boarding
8.5Crew
7.4Food
Airline reviews

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.

8.0 ExcellentAnonymous, Aug 2026
Read more Air New Zealand reviews

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.

Time to upgrade those planes so you can provide first class.

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.

This flight was the second leg of a trip that began in Auckland, New Zealand. I was unable to find a way to select seats in advance. The boarding passes we were given in Auckland did not have seat assignments for the second flight. There was no way to check on it until personnel showed up at the gate in Los Angeles, immediately before boarding time. The flight was overbooked by one, and since I was traveling with my sister, we needed two seats. We waited in considerable anxiety for everyone else to board and when one person did not show up, we had to take whatever was left. At least we finally got on the flight although we were the very last to board. We were not able to sit together, of course.

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.

We had difficulty checking in as United didn’t recognize the confirmation number and the agent was not helpful. We went to the United Assistance desk where the agent was able to process our reservation. We also weren’t allowed to choose seats in advance.

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!

Couldn’t request a vegan meal somehow but I noticed other people getting them

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.

Great food and good entertainment options for the long flight.

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

Very good overall. Highly recommend for all flying to Australia

We had bulkhead seats in a A380 in the upper deck in seats 31 D and E. Storage was very limited other than in overhead bin - which is not within reach when in seat. Yet paying same price as others in premium economy who have a lot more storage within arm’s reach. Seems very unfair.

Good check in and helpful staff. Delayed for 1 hour. Took about 45 Mins to get baggage’s at DFW . Food was average ( Hindu meal ) . Overall it was good experience

When I originally booked this flight, I was expecting to travel on Qantas. When the itinerary changed and the long-haul segment was operated by American Airlines, we were disappointed but remained open-minded. Unfortunately, the overall service experience fell far short of expectations. This was a long-haul international flight. Getting up periodically to use the restroom or stretch is inevitable, especially on flights of this duration. However, each time we stood up, we felt as though we were inconveniencing the crew. The tone and body language often suggested that we were in the way or disrupting something simply by moving about the cabin. As a result, I avoided getting up as often as I needed to and was physically very sore upon arrival. Meal service was similarly impersonal. The options were presented in single words “beef or veggie,” “pasta or beef” without any description of what was actually being served. There was little engagement or courtesy beyond that. Even simple expressions of gratitude were often not acknowledged. I am accustomed to no-frills travel and do not expect luxury. What was disappointing was not the absence of extras, but the absence of basic warmth and professionalism. On a long-haul international flight, small moments of courtesy and humanity make a significant difference. In this case, the experience felt transactional and dismissive rather than welcoming. I hope this feedback is taken constructively, as there is a meaningful difference between efficient service and indifferent service.

Business seats not as comfortable or private as most competitors (e.g. Qantas was outstanding), and movie selection was much more limited than Qantas or United has been recently

Hard to move and get out of my seat when the passenger in front is in recline position.

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.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Travelling to a place near Chicago?

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

More options for your flight to Chicago