$622 Find Cheap Flights to Chicago – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 17% 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 flight
$1,056
Typical prices: $1,534-$2,408
American Airlines
Mon 5/11Fri 9/11
SYD - ORD • 1 stop
Cheapest one-way flight
$622
Typical prices: $1,130-$1,710
Delta
Mon 26/11
SYD - ORD • 1 stop
Top airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
Top routes
Cheapest • 23% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 20 weeks in advance save around 24% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 13% price drop
Most popular
Good to know
+1
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 enjoy 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

Thu, 5 Nov - Mon, 9 Nov
American Airlines Logo
11:10 - 17:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 49m1 stop Los Angeles
American Airlines Logo
17:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
22h 31m2 stops Phoenix Sky Harbor Intl Los Angeles
$1,056American Airlines
Thu, 5 Nov - Mon, 9 Nov
American Airlines Logo
11:10 - 17:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 49m1 stop Los Angeles
American Airlines Logo
10:32 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 28m1 stop Los Angeles
$1,056American Airlines
Tue, 17 Nov - Tue, 24 Nov
Delta Logo
10:40 - 16:41SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 01m2 stops Los Angeles Minneapolis St Paul
Delta Logo
14:44 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 46m2 stops Detroit Metropolitan Wayne County Los Angeles
$1,065Delta
Tue, 17 Nov - Tue, 24 Nov
Delta Logo
10:40 - 20:49SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
27h 09m2 stops Los Angeles Atlanta Hartsfield-Jackson
Delta Logo
14:32 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 58m1 stop Los Angeles
$1,065Delta
Fri, 6 Nov - Mon, 23 Nov
Qantas Airways Logo
11:10 - 16:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 55m1 stop Los Angeles
Qantas Airways Logo
08:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 31m1 stop Los Angeles
$1,151Qantas Airways
Fri, 6 Nov - Mon, 23 Nov
Qantas Airways Logo
11:10 - 22:30SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
28h 20m1 stop Los Angeles
Qantas Airways Logo
15:21 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 39m2 stops Denver Intl Los Angeles
$1,211Qantas Airways
Thu, 22 Oct - Sat, 7 Nov
Air Canada Logo
10:00 - 16:35BNE  Brisbane-ORD Chicago O'Hare Intl
21h 35m2 stops Vancouver Intl Winnipeg
Air Canada Logo
17:54 - 08:45ORD  Chicago O'Hare Intl-BNE Brisbane
46h 51m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$1,356Air Canada
Mon, 9 Nov - Sun, 7 Feb
Air Canada Logo
10:45 - 19:52BNE  Brisbane-ORD Chicago O'Hare Intl
25h 07m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
07:05 - 08:45ORD  Chicago O'Hare Intl-BNE Brisbane
33h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$1,358Air Canada
Tue, 10 Nov - Tue, 17 Nov
Air New Zealand Logo
07:30 - 22:00SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
31h 30m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
09:21 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 14m2 stops Houston George Bush Intcntl Auckland Intl
$1,700Air New Zealand
Fri, 6 Nov - Mon, 23 Nov
Air New Zealand Logo
14:05 - 00:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
27h 54m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
15:00 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 35m2 stops Los Angeles Auckland Intl
$1,746Air New Zealand
Booking Insights

Price, demand, and travel trends for flights to Chicago

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What is the cheapest flight to Chicago?

Sydney to Chicago is the cheapest route at $1,056 return, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.

How much is a flight to Chicago?

On average, a return flight from Australia to Chicago costs $1,851, based on KAYAK data over the past 12 months. Return fares from Melbourne Airport average $1,651, while Sydney runs a bit higher at $1,790.

What is the cheapest day to fly to Chicago?

Tuesday is the cheapest day to fly to Chicago at $1,752 return on average over the past 12 months on KAYAK. Saturday is the most expensive at $2,141.

What is the cheapest month to fly to Chicago?

•March is the cheapest month to fly to Chicago with an average price of $1,609 return.
•December ($2,127) and July ($2,094) are the most expensive.
•Based on KAYAK data over the past 12 months.

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

Afternoon flights to Chicago are the cheapest at $1,706 return on average. Night flights are the most expensive at $2,206.

What is a good deal for flights to Chicago?

Flights under $1,534 are considered a good deal. 25% of KAYAK users found return flights to Chicago at or below these prices, with the lowest fares from:
•Melbourne Airport $1,446
•Sydney $1,525.

When are flights to Chicago the cheapest?

Flights to Chicago are cheapest 20 weeks before departure. Booking in this window typically costs about 24% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for flights to Chicago

Low season

February

Cheapest flight

$622
Beat the crowds with an average 45% drop in traveller numbers.
The most popular month to fly with an average 28% increase in traveller numbers.
One-way flight from Sydney to Chicago O'Hare Intl 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

Your questions about flights to Chicago, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Chicago is a good deal?

    A good deal on a flight to Chicago is around $1,534 return. This fare is in the lowest 25% of return flight prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • How far are the airports serving Chicago from the city centre?

    Chicago is served by multiple airports. Chicago Midway is 14.3 km from Chicago city centre, Chicago O'Hare Intl is 25.3 km from Chicago city centre, and Chicago Greater Rockford is 126.1 km from Chicago city centre.

  • Which airports serve Chicago?

    Flights to Chicago arrive at: Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • How expensive are last-minute flights to Chicago?

    Last-minute fares to Chicago (booked within two weeks of departure) are typically 5% higher than the average return fare of $1,851.

  • What is the difference between the most popular and the most frequent airline at Chicago?

    United Airlines operates the most flights from Australia to Chicago at 0 per week, while Qantas Airways is the airline most often selected by KAYAK users searching for flights from Australia to Chicago. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80.5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

  • 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.

Your guide to booking Chicago flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Chicago, book around 20 weeks before departure. Based on KAYAK data from the last 12 months, fares are historically about 24% lower during this window than last-minute fares.
  • For flights to Chicago, a good return fare is around $1,534. If you find a fare below that, you're getting a strong deal.
  • If your travel dates are flexible, consider flying to Chicago in March. Return fares historically average $1,609, making March the cheapest month to travel based on KAYAK data from the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to midday to save up to $500 on a return flight. Midday flights to Chicago average $1,706 compared to $2,206 for evening flights.
  • Once you arrive in Chicago, a few great places to start are River North, Millennium Park, and Chicago Water Tower. These are popular with first-time visitors and can give you a good feel for the area.
  • 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 669 reviews
8.2Boarding
7.5Food
7.9Comfort
8.5Crew
7.4Entertainment
Airline reviews

Premium economy seats and food we're very nice although the price could be more affordable so we can do it more often.

10.0 ExcellentSharon, Sept 2026
Read more Air New Zealand reviews

Premium economy seats and food we're very nice although the price could be more affordable so we can do it more often.

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.

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.

Raleigh to Chicago was OK. The problem was Chicago to Lincoln. Flight was delayed 4 hours. Give them credit for the updates and reason why it was delayed

Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

After having bad experience last time This time they were very good

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Snacks and drinks should be served together and air hostess was not supportive with no smile which was kind of disappointing.

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…

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

My experience was fine, with one surprising exception. After leveling off at cruising altitude, the main cabin flight attendant made an announcement that he had a cold, so he would not be coming through the aisle to provide cabin service. He claimed this was in consideration of his health and safety and ours. However, if passengers wanted a beverage, he invited them to come to the back of he plane, where he would provide service. I understand that a flight attendant's primary responsibility is to ensure passenger safety, but a secondary role is to provide service. If this flight attendant was too sick to perform his duties - and if he truly cared about passenger health and safety , as he claimed - he should have stayed home and called in sick, rather than exposing the cabin to his germs.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

We waited over 30 minutes for a gate in Chicago and more than 15 minutes for the doors to open. Cookies were missing from the menu.

Flight was 2 hr late but at least I was upgraded to first class

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

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