$614 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
$1,043
Typical prices: $1,597-$2,476
American Airlines
Sat 17/11Sun 2/12
SYD - ORD • 1 stop
Cheapest one-way flight
$614
Typical prices: $1,155-$1,751
Delta
Sat 14/4
SYD - ORD • 1 stop
Top airlines
Best reviews • 7.6 score
Airline reviews
Airline reviews
Top routes
Cheapest • 19% average savings
Most popular
Insights
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When to book
in advance
Our data shows that travellers who book at least 20 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
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Cheap Flights to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Tue, 17 Nov - Wed, 2 Dec
American Airlines Logo
11:10 - 16:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 55m1 stop Los Angeles
American Airlines Logo
13:30 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
26h 30m1 stop Los Angeles
$1,043American Airlines
Thu, 12 Nov - Mon, 16 Nov
American Airlines Logo
11:10 - 06:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
35h 55m1 stop Los Angeles
American Airlines Logo
21:04 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 56m1 stop Los Angeles
$1,044American Airlines
Fri, 29 Jan - Sun, 7 Feb
Delta Logo
10:40 - 18:09SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
24h 29m2 stops Los Angeles Salt Lake City
Delta Logo
13:10 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
26h 20m2 stops Salt Lake City Los Angeles
$1,120Delta
Wed, 18 Nov - Thu, 3 Dec
Delta Logo
10:40 - 21:33SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
27h 53m2 stops Los Angeles Minneapolis St Paul
Delta Logo
18:10 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 20m1 stop Los Angeles
$1,121Delta
Tue, 2 Feb - Fri, 5 Mar
Philippine Airlines Logo
11:30 - 16:55SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
46h 25m1 stop Manila Ninoy Aquino Intl
Philippine Airlines Logo
22:45 - 09:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 05m1 stop Manila Ninoy Aquino Intl
$1,426Philippine Airlines
Mon, 9 Nov - Mon, 23 Nov
Philippine Airlines Logo
08:35 - 16:55PER  Perth-ORD Chicago O'Hare Intl
22h 20m1 stop Manila Ninoy Aquino Intl
Philippine Airlines Logo
22:45 - 07:20ORD  Chicago O'Hare Intl-PER Perth
42h 35m1 stop Manila Ninoy Aquino Intl
$1,482Philippine Airlines
Thu, 12 Nov - Tue, 17 Nov
Cathay Pacific Logo
15:30 - 12:30MEL  Melbourne-ORD Chicago O'Hare Intl
38h 00m1 stop Hong Kong Intl
Cathay Pacific Logo
14:10 - 23:05ORD  Chicago O'Hare Intl-MEL Melbourne
39h 55m1 stop Hong Kong Intl
$1,739Cathay Pacific
Tue, 10 Nov - Tue, 17 Nov
Cathay Pacific Logo
00:45 - 12:30MEL  Melbourne-ORD Chicago O'Hare Intl
28h 45m1 stop Hong Kong Intl
Cathay Pacific Logo
14:10 - 23:05ORD  Chicago O'Hare Intl-MEL Melbourne
39h 55m1 stop Hong Kong Intl
$1,739Cathay Pacific
Mon, 1 Feb - Mon, 22 Feb
Qantas Airways Logo
06:25 - 16:54ADL  Adelaide-ORD Chicago O'Hare Intl
26h 59m2 stops Brisbane Los Angeles
Qantas Airways Logo
16:59 - 13:30ORD  Chicago O'Hare Intl-ADL Adelaide
28h 01m2 stops Los Angeles Melbourne
$1,766Qantas Airways
Wed, 3 Feb - Mon, 22 Feb
Qantas Airways Logo
06:25 - 19:56ADL  Adelaide-ORD Chicago O'Hare Intl
30h 01m2 stops Brisbane Los Angeles
Qantas Airways Logo
15:25 - 13:30ORD  Chicago O'Hare Intl-ADL Adelaide
29h 35m2 stops Los Angeles Melbourne
$1,766Qantas Airways
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 $1,043 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 $1,944, based on KAYAK data over the past 12 months. Return fares from Melbourne average $1,745, while Sydney runs a bit higher at $1,853.

What is the cheapest day to fly to Chicago?

Sunday is the cheapest day to fly to Chicago at $1,885 return on average over the past 12 months on KAYAK. Saturday is the most expensive at $2,140.

What is the cheapest month to fly to Chicago?

•March is the cheapest month to fly to Chicago with an average price of $1,620 return.
•December ($2,256) and September ($2,113) 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 $1,712 return on average. Night flights are the most expensive at $2,347.

What is a good deal for flights to Chicago?

Flights under $1,597 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 $1,502
•Sydney $1,553.

When are flights to Chicago the cheapest?

Flights to Chicago are cheapest 20 weeks before departure. Booking in this window typically costs about 30% 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

$614
Beat the crowds with an average 57% drop in travellers.
The most popular month to fly with an average 69% increase in travellers.
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 $1,597 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).

  • Which city has the cheapest flights to Chicago?

    Based on fares booked in the past 5 days, the cheapest flights to Chicago are from Melbourne, starting at $1,739 return.

  • How expensive are last-minute flights to Chicago?

    Last-minute fares to Chicago (booked within two weeks of departure) are typically 8% higher than the average return fare of $1,944.

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

    American 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 30% lower during this window than last-minute fares.
  • For flights to Chicago, a good return fare is around $1,597. 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 $1,620, 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 $635 on a return flight. Midday flights to Chicago average $1,712 compared to $2,347 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 679 reviews
7.9Comfort
7.4Food
7.4Entertainment
8.2Boarding
8.5Crew
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.

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

The first leg of my trip the Republic Airlines aircraft was late due to a maintenance problem. Then I called United to reroute. Their reroute airline lost my bag but found it and returned it two days later. Hopefully my return trip home is better.

No problems other than no seat back entertainment. Everyone was very pleasant

No notes; this was an excellent flight that was quick and comfortable!

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.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

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