$825 Find Cheap Flights to Chicago – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

Save 16% 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
$1,298
Typical prices: $1,512-$1,682
Multiple Airlines
Wed 12/8Wed 19/8
SYD - ORD • 2 stops
Cheapest one-way flight
$825
Typical prices: $1,083-$1,140
Multiple Airlines
Wed 12/8
MEL - ORD • 3 stops
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 66% 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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Wed, 12 Aug - Wed, 19 Aug
Multiple Airlines Logo
06:05 - 06:17
SYD
-
ORD
39h 12m
2 stops
Multiple Airlines Logo
09:20 - 11:50
ORD
-
SYD
35h 30m
3 stops
$1,298Multiple Airlines
Fri, 7 Aug - Fri, 21 Aug
Qantas Airways Logo
09:45 - 16:51
MEL
-
ORD
22h 06m
1 stop
Qantas Airways Logo
17:16 - 06:45
ORD
-
MEL
22h 29m
1 stop
$1,316Qantas Airways
Sat, 15 Aug - Sat, 22 Aug
Qantas Airways Logo
09:45 - 15:54
MEL
-
ORD
21h 09m
1 stop
Qantas Airways Logo
15:54 - 05:00
ORD
-
MEL
22h 06m
1 stop
$1,321Qantas Airways
Sat, 1 Aug - Sat, 8 Aug
American Airlines Logo
09:45 - 16:00
MEL
-
ORD
21h 15m
1 stop
American Airlines Logo
17:16 - 06:45
ORD
-
MEL
22h 29m
1 stop
$1,337American Airlines
Wed, 29 Jul - Wed, 26 Aug
American Airlines Logo
09:45 - 15:59
MEL
-
ORD
21h 14m
1 stop
American Airlines Logo
14:57 - 05:00
ORD
-
MEL
23h 03m
1 stop
$1,339American Airlines
Mon, 3 Aug - Wed, 19 Aug
Air New Zealand Logo
09:55 - 22:59
SYD
-
ORD
28h 04m
2 stops
Air New Zealand Logo
16:20 - 08:45
ORD
-
SYD
25h 25m
2 stops
$1,656Air New Zealand
Wed, 12 Aug - Wed, 19 Aug
Air New Zealand Logo
11:55 - 21:30
SYD
-
ORD
24h 35m
2 stops
Air New Zealand Logo
16:20 - 08:45
ORD
-
SYD
25h 25m
2 stops
$1,677Air New Zealand
Thu, 13 Aug - Thu, 20 Aug
Fiji Airways Logo
11:55 - 21:16
BNE
-
ORD
24h 21m
2 stops
Fiji Airways Logo
17:50 - 10:40
ORD
-
BNE
25h 50m
2 stops
$1,941Fiji Airways
Thu, 27 Aug - Mon, 31 Aug
Air Canada Logo
20:00 - 14:36
ADL
-
ORD
33h 06m
2 stops
Air Canada Logo
15:40 - 11:50
ORD
-
ADL
29h 40m
2 stops
$2,660Air Canada
Tue, 25 Aug - Thu, 1 Oct
Air Canada Logo
20:00 - 14:36
ADL
-
ORD
33h 06m
2 stops
Air Canada Logo
08:49 - 15:55
ORD
-
ADL
40h 36m
2 stops
$2,663Air Canada
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?

These are the best round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Melbourne, at $1,298 return. The most popular connection is from Sydney to Chicago and KAYAK users have found return deals for as low as $1,298 in the last 3 days.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is September, where tickets cost $178 on average for return flights. On the other hand, the most expensive months are January and March, where the average cost of tickets from Australia is $1,219 and $1,022 respectively. For one-way flights, the best month to travel is August with an average price of $184.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 2 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 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 Greater Rockford Airport (RFD), with an average flight price of $138.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight$825
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (16% more expensive on average)
Flight from Melbourne 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

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 3 days, the cheapest flight deal to Chicago was found on the route from Melbourne, at $1,298 return. The most popular connection is from Sydney to Chicago and KAYAK users have found return deals for as low as $1,298 in the last 3 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

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Australia to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 649 reviews
7.9Comfort
7.4Entertainment
8.5Crew
7.4Food
8.2Boarding
Airline reviews

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

8.0 ExcellentAnonymous, Apr 2026
LFT - IAH
Read more Air New Zealand reviews

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!

Very quick flight so no time for refreshments. We took off. Then landed. The end. Seats were too tight. Very cramped Grateful for the short flight cos moving around wasn’t possible

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.

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.

Basic airline, aircraft and service. AA gets you from point A to B. My flight was delayed by 2 hours too.

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.

The flight was delayed an hour and a half while you tried to fix the plane so I missed my connecting flight in Chicago. In Chicago, it took an hour to get the luggage. Then the conveyor belt was broken where I have to transfer my flight from an international flight to the continuing flight so I had to carry a large suitcase through the airport. The elevators were broken in the airport. I paid people to carry the luggage for me up the escalators in two different areas. The person who helped me get the new flight was outstanding. The temperature in the airport in Chicago was horrible. We were all sweating. It was the day from hell. That was after two hours in a security line in Athens. I have TSA pre-checked and global entry and I still waited. Two hours in a security line. Something has got to be done to stream line this service. After I’ve been through all of that in Athens, why do I have to go through it again in Chicago. It was the worst travel experience I have had in a long time. Your bathrooms have gotten so small that you can hardly get your butt on the toilet. You’ve taken the airspace out of the inside of the top of the toilet. It really makes for a miserable experience. Also on a 4 1/2 hour flight from Chicago to Los Angeles. The only thing we’re given is a bag of pretzels. REALLY!!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

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
New Buffalo
Benton Harbor
Hammond

Everything you need to know for your flight to Chicago

Flights with popular airlines flying to Chicago

Flights from the other most popular airlines that fly from Australia to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.