$730 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 1/5. 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.
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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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Cheap Flight Deals 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.

Recent return flight deals to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
09:20 - 20:14SYD-ORD
25h 54m2 stops
10:40 - 07:20ORD-SYD
29h 40m2 stops
$1,326Air Canada
Find Deal
Tue, 29 Jul - Tue, 12 Aug
09:20 - 07:59SYD-ORD
37h 39m2 stops
15:35 - 07:20ORD-SYD
24h 45m1 stop
$1,331Air Canada
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Tue, 29 Jul - Mon, 4 Aug
11:55 - 05:53MEL-ORD
32h 58m1 stop
13:22 - 05:00ORD-MEL
24h 38m2 stops
$1,491American Airlines
Find Deal
Wed, 7 May - Sun, 18 May
09:45 - 05:13MEL-ORD
34h 28m2 stops
13:28 - 05:00ORD-MEL
24h 32m1 stop
$1,567American Airlines
Find Deal
Mon, 5 May - Wed, 30 Jul
20:05 - 22:32BNE-ORD
41h 27m1 stop
08:39 - 05:25ORD-BNE
29h 46m1 stop
$1,646Qantas Airways
Find Deal
Wed, 14 May - Wed, 21 May
09:45 - 23:55MEL-ORD
29h 10m1 stop
17:52 - 06:45ORD-MEL
21h 53m1 stop
$1,684Qantas Airways
Find Deal
Mon, 16 Jun - Tue, 1 Jul
09:30 - 00:15SYD-ORD
29h 45m2 stops
17:50 - 07:00ORD-SYD
22h 10m1 stop
$1,738United Airlines
Find Deal
Tue, 22 Apr - Tue, 29 Apr
10:55 - 20:25MEL-ORD
24h 30m2 stops
16:30 - 08:15ORD-MEL
24h 45m2 stops
$1,811United Airlines
Find Deal
Tue, 24 Jun - Fri, 27 Jun
21:35 - 19:33PER-ORD
34h 58m2 stops
17:45 - 15:45ORD-PER
33h 00m2 stops
$2,006ANA
Find Deal
Thu, 4 Sep - Mon, 8 Sep
12:50 - 19:39SYD-ORD
46h 49m2 stops
17:45 - 19:15ORD-SYD
34h 30m1 stop
$2,266ANA
Find Deal
Tue, 1 Apr - Thu, 8 May

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 day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as $2,002. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $2,311 on average.

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 February, where tickets cost $1,203 on average for return flights. On the other hand, the most expensive months are December and September, where the average cost of tickets from Australia is $2,418 and $1,868 respectively. For one-way flights, the best month to travel is April with an average price of $2,009.

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

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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.

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. 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 Midway Airport (MDW), with an average flight price of $487.

Good to know – Book Cheap Chicago Plane Tickets

Low season

February

High season

June

Cheapest flight

$730
Best time to beat the crowds (26% less expensive on average)
Most popular time to fly (11% 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
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.

  • 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.

See more FAQs

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.
See more tips

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.
8.3
ANAOverall score based on 828 reviews
8.5Boarding
8.2Comfort
7.7Food
7.9Entertainment
8.7Crew
Airline reviews

Uh there was a delay, because of the weather. And what took usually an hour flight to Louisville took about 6+ hours. Flight got canceled

2.0 MediocreAnonymous, Mar 2025HND - ORD
Read more ANA reviews

Uh there was a delay, because of the weather. And what took usually an hour flight to Louisville took about 6+ hours. Flight got canceled

I had to get rerouted because the weather delayed my flight enough to miss both of my connecting flights. I select nearly 2 hours on customer service trying to get rerouted and had to miss my first plane which took my luggage to San Francisco. Luckily, customer service sent me to the same airport but I had to ride 12 hours in economy after I paid extra for premium economy. Totally sucks that I overpaid. Customer service and airplane crew were great and really helpful though. Although I still hate how small the seat was, especially since I'm smaller than average, I can't imagine how much it would suck for an average sized person.

Flight attendant took good care of my mom as she boarded on and off the aircraft from her wheelchair. I did not care much for the food nor the movie options Available. I appreciated the increased legroom available in economy. This was one of the main reasons we chose the airline. Overall, the good value and I would fly again.

I stopped flying with United back in the nineties. Today's experience reminded me of why.

ANA was fine. LAX has some major problems. I needed a wheelchair and BKK and Narita were very good. I do have to remember NOT to tip in Japan. LAX however, was poor. first the attendant wasn't able to push me. The next person left me stranded in several locations. They would just leave me where ever they felt like; No logic to these locations. finally when we cleared immigration, they (there were several people who didn't seem to care about their job) left me in a large room with a baggage carousal. I tried to locate my luggage to no avail. meanwhile my connection was getting closer. I finally talked with Emir from ANA and he showed me to my carousal which was located a few rooms away from where LAX personnel stranded me. Emir also found a good wheelchair attendant to take me the rest of the way. Without Emir from ANA, I would still be stranded, given the amount of care shown by the first wheelchair attendants.

Great airline all together - triple 7 for a short flight was a plus - lots of room

Seat width can be a bit wider. not nice that they charge extra for the window seats. online check in can be greatly improved. in other words, their online interface is bad.

Seats were comfortable with excellent legroom. Meals were also quite good. The cabin crew were excellent and very helpful. The check-in experience was also very smooth.

I was very happy with my flight on ANA. The crew were excellent and very helpful throughout the flight. The food was also very good. The seats were comfortable and had excellent legroom. The headphone jack position was annoying, but that is a minor nitpick. The movie selection in the IFE was good, but the TV selection was lacking. Adding English subtitles to the Japanese movies and videos would have been very useful.

The cabin was hot. I was sweating during the whole trip.

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.

Virgin changed the flight to an Alliance flight. Smaller plane, tea coffee and water the only refreshments available and not sure what happened to the extra money I paid to sit in a selected seat with extra leg room. This is obviously a regular switch as it happened on our flight there and back. Do not recommend.

Late boarding, late departure due to weather and slow boarding, packed 5+hour flight, only 2 toilets for main cabin, tight leg room, no free food except tea, coffee, and water, arrived 75 minutes late.

Cramped, crowded flight, with no complimentary food except coffee, tea, or water.

Check-in was good and efficient, Boarding was quick and easy. Didn't like the entertainment side of things requiring your phone to connect for a screen, my eyes are bad enough to use my phone more than I already do. Trip was comfortable and baggage claim was good. If coffee and tea were free, then why not a soda or juice as well, its not like its an alcoholic drink.

Very good as always, stand out airline. The passengers whom choose to stuff baggage that otherwise should be checked-in is a real bother but that's not the airlines doing. A real frustration that passengers just don't want to check-in luggage. This is a pet hate unfortunately.

It’s a two prop flight so I had problems with my ears on re- entering ! But otherwise fine

I love flying with Qantas. There was no onscreen entertaining on this flight, and only a snack provided (not a meal) but still better than Jetstar or Virgin (in my opinion) so still happy.

Complaint is with American Airlines which delayed our flight from salt lake to Dallas reaulting in us missing our connection to Brisbane. Had to spend 24 hours in Dallas to wait for the next flight. Awful experience and ruined my wife’s birthday.

Wheelchair assistance to move through the terminals and to/from the plane door was excellent. No vegan snack on the flight, only something with salami and cheese in it.

The old Plane had not been cleaned properly in a long time.

Planes was old - business class seats looked like they were installed in the 80s

Our baggage didn’t arrive with us on the plane. Need I say more?

I got upgraded from economy to business, and the experience was outstanding

I have taken this flight many times. It is ALWAYS late. Every time there is significant delay (1-3 hours) before boarding. It’s very consistent. Even after boarding the expected landing time was delayed twice. The seats are very narrow and cramped. Food is barely editable. Considering an economy ticket often costs about $2,000 it’s one of the worst services ever.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

I paid for a comfort class seat and was seated in economy.

Once again our Air Canada flight was delayed! I'm hopeful competition arrives with other airlines soon and maybe they will make a better effort to be on time!

My plane was cancelled and had to be rebook for the evening was not happy.

The flight was cancelled and we had to rebook on Porter to make our cruise the next day. Air Canada has not compensated. We won’t be flying with them again. This is the second time this has happened. Also the return flight was delayed 2 hours who knows why.

Mixed experienced. Nice staff. Spacious 787 better than cramped Airbus, though my seat was broken. The bad: Way overpriced ticket and charged for food despite 6 hr flight.

Separated me and my wife and wife’s sister in far apart different seats even though I booked them all together. Just scams after scams to make us pay more. Worst airline

Very smooth flight and the crew members were very welcoming.

The only issues I have are the seats are very small and so is the overhead storage. You should mention that while booking flights. I had plenty of knee room but I am wider than my seat, and I am not fat at all. The Mitsubishi 900 models need to be upgraded to western size people. I do not know how a 300 pound woman fit into those seats. I had to continuously lean away from the aisle to keep people and flight crew from bumping into my shoulder. 3 hour flight so no entertainment or food, just snacks and a drink, which was no big deal. The buttery/garlic pretzels were pretty tasty.

If you want your flight to get delayed constantly for 13+ hours and given a 10 dollar food voucher the. I would say take air canada. Worst experience ever.

My flight was cancelled and I was left to figure out where to find a hotel, something to eat and how to get a new flight at 11:30pm. Wasted a day. Thanks, Air Canada!

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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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