$637 Find Cheap Flights to Chicago

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 15/10. 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

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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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

Tue, 17 Feb - Thu, 26 Feb
Air Canada Logo
10:45 - 19:30BNE-ORD
24h 45m2 stops
Air Canada Logo
08:00 - 08:45ORD-BNE
32h 45m2 stops
$1,212Air Canada
Find Deal
Tue, 17 Feb - Thu, 26 Feb
Air Canada Logo
10:45 - 14:41BNE-ORD
19h 56m1 stop
Air Canada Logo
08:00 - 08:45ORD-BNE
32h 45m2 stops
$1,227Air Canada
Find Deal
Tue, 30 Sep - Wed, 12 Nov
Qantas Airways Logo
09:10 - 15:51SYD-ORD
21h 41m1 stop
Qantas Airways Logo
18:03 - 09:00ORD-SYD
21h 57m1 stop
$1,419Qantas Airways
Find Deal
Sat, 15 Nov - Sun, 16 Nov
United Airlines Logo
12:10 - 19:01SYD-ORD
23h 51m2 stops
United Airlines Logo
12:45 - 09:15ORD-SYD
27h 30m1 stop
$1,437United Airlines
Find Deal
Wed, 8 Oct - Wed, 29 Oct
Air New Zealand Logo
09:55 - 23:12SYD-ORD
29h 17m2 stops
Air New Zealand Logo
15:40 - 10:30ORD-SYD
26h 50m2 stops
$1,495Air New Zealand
Find Deal
Thu, 13 Nov - Tue, 18 Nov
Air New Zealand Logo
12:10 - 22:59MEL-ORD
27h 49m2 stops
Air New Zealand Logo
13:00 - 17:40ORD-MEL
35h 40m2 stops
$1,518Air New Zealand
Find Deal
Thu, 16 Oct - Mon, 3 Nov
United Airlines Logo
11:55 - 20:07MEL-ORD
24h 12m1 stop
United Airlines Logo
16:40 - 09:30ORD-MEL
23h 50m1 stop
$1,566United Airlines
Find Deal
Wed, 26 Nov - Tue, 27 Jan
Qantas Airways Logo
17:45 - 23:59SYD-ORD
23h 14m1 stop
Qantas Airways Logo
12:25 - 06:10ORD-SYD
24h 45m1 stop
$1,584Qantas Airways
Find Deal
Fri, 31 Oct - Fri, 7 Nov
Virgin Australia Logo
06:00 - 19:30OOL-ORD
28h 30m2 stops
Virgin Australia Logo
17:16 - 18:00ORD-OOL
32h 44m3 stops
$2,598Virgin Australia
Find Deal
Sun, 8 Mar - Wed, 11 Mar
Virgin Australia Logo
06:10 - 15:40ADL-ORD
26h 00m2 stops
Virgin Australia Logo
18:00 - 13:00ORD-ADL
27h 30m2 stops
$2,925Virgin Australia
Find Deal

Everything you should know

When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 21% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 27% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
$1,212
Overall average: $1,071
Air Canada
Tue 17/2Thu 26/2
BNE - ORD • 2 stops
Cheapest one-way flight
$637
Typical prices: $829-1419
Multiple Airlines
Wed 15/10
SYD - ORD • 2 stops
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!
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 month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for 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 March, where tickets cost $1,110 on average for return flights. On the other hand, the most expensive months are December and January, where the average cost of tickets from Australia is $2,294 and $1,910 respectively. For one-way flights, the best month to travel is May with an average price of $1,812.

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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 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 $143.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight$637
Best time to beat the crowds (2% less expensive on average)
Most popular time to fly and prices are also 4% lower 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
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.

  • 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $1,893. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $2,161 on average.

  • 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.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost $1,121 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,240.

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 505 reviews
8.0Comfort
7.3Food
8.5Crew
7.4Entertainment
8.2Boarding
Airline reviews

Not a comfortable trip, the seats are not good, and they look old.

4.0 OkayAnonymous, July 2025AKL - SFO
Read more Air New Zealand reviews

Not a comfortable trip, the seats are not good, and they look old.

Lost my luggage and brought someone else luggage to my airport.

Not entirely positive. It’s frustrating that everything is done through the united app. One of our flight attendants on our trip from San Francisco to MSP continually had trouble hearing people so she flipped her hair into people’s faces

I flew United from San Francisco to Auckland. My connecting flight from Auckland to Christchurch was canceled with no explanation. I was finally told the cancellation was due to fog. Even though it was clear when we landed. I am from San Francisco, I know what fog is! And I didn't see any fog. I was told the next available flight was 7 hours later. Unacceptable, they should have had a flight ready to go as soon as it was deemed safe to take off.

Our original flight was cancelled from SFO to AKL on 6/16/25. So we had to stay overnight at a hotel after a 12-hour layover plus 3-hour delay before the cancellation. Then had to fly to LA and then to AKL the following day losing an entire day of our vacation in NZ, that we can never get back.

Full flight. Flight attendants were harried. Otherwise, fine for the typical cramped seating conditions in coach.

The 10hr flight was a comfortable as it could be in row 57. The food was just very bad….bland and soggy!

The business class upgrade meant a good sleep on the way home after a long week away. Excellent service, great food, and comfortable seat/bed for the journey.

I love the “boarding from the back” idea - it’s so much better than the “Zones” idea that many others use. Also, the inflight wifi was a first for me! Very nice to have on a 13-hour flight!

Again, Air New Zealand was great. They kept bathrooms clean, food was actually very good, New Zealand wines a big hit

Overall experience was good but what really impressed me the most was the care the flight attendants took of a sick passenger who was sitting in front of me. The flight attendants would come and check on her quite regularly providing her support and comfort. Brilliant service!

Only answered OK and poor as there was no entertainment and I didnt have any food

4.5 hr international flight. We got a glass of water. Ranks up there with Ryan Air, Easy Jet, Spirit and Frontier. Expected better.

Gluten free options less explicit on business class, but great service

Very good… seems the virgin staff particularly in the lounge and in flight exceeded expectations.

I liked everything about the experience but would have liked some free snacks!

Crew was great but flight was delayed almost three hours due to a technical issue and we had to go back to the terminal and wait for another one.

Being told why we delayed three hours and not even given an apology by someone. Not a word. Not my airline of choice ever.

Checked Baggage line up was long but moved quickly, rest of the process, boarding, crew was excellent

Virgin has always provided a smooth and comfortable flight. This one was no different. Seats are comfortable. Staff are great. This is my favourite airline.

My flight from Dallas to Sydney was cancelled. My entire trip was rerouted to include the following: Hartford to Washington DC Washington DC to JFK JFK to Auckland Auckland to Christchurch I paid for an aisle seat on the flight to Auckland and was asked if I would take a window seat to accommodate a family. The agent at the podium failed to mention that the family had a 3 month old baby and that a bassinet would be used during the 16 hour flight. The only way I could get out of my seat was to crawl under the bassinet of the sleeping baby. I think it is wrong that I was no given the choice to sit in another seat, that the agent knew what she was doing and chose to not properly disclose my seating arrangement. Terrible treatment.

they ran out of fruit for breakfast and so I just had a yogurt instead. other than that the flight was good

by the time they got to our row, they were out of some of the food options. games and movies were great but maybe more game options like tetris or pac man would be great

A few more inches of legroom is all i ask

Great as usual, some delays but well communicated and made up for in the air

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.

Business class points redemption - good value for points paid, dubious value if out of your own pocket, domestic class business product okay for this length of flight. The flight left and arrived on time, crew were good, aircraft was a bit old and tired, but still miles ahead of their competitors in Virgin and Jetstar.

Airline running better than post Covid, proper boarding process now implemented, some aircraft feeling a bit old and tired, crew fine, online experience better.

We were upgraded and after just a short delay in attending to a safety check we were on our way. Would definately fly Qantas International on their Dreamliner again.

Five hour flight instead of four hours due to westerly headwinds which wasn’t the fault of Qantas !

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

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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.

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