To Sydney

Cheap Flights from Chicago to Sydney

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Sydney

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Sydney

Explore current cheapest deals departing from Chicago to Sydney

Round trip

Sort by: Cheapest

August 7 - August 18

Cheapest

Earliest

ORD - Sydney

$1,195

$1,104

Round trip

August 11 - August 20

ORD - Sydney

$1,222

$1,118

Round trip

November 2 - November 10

Best

ORD - Sydney

$1,288

$1,131

Round trip

September 9 - September 30

ORD - Sydney

$1,221

$1,136

Round trip

September 1 - September 20

ORD - Sydney

$1,200

$1,137

Round trip

August 12 - August 20

ORD - Sydney

$1,229

$1,140

Round trip

November 10 - November 19

Best

ORD - Sydney

$1,291

$1,177

Round trip

August 19 - August 24

ORD - Sydney

$1,295

$1,179

Round trip

August 9 - August 22

ORD - Sydney

$1,200

$1,181

Round trip

August 18 - August 24

ORD - Sydney

$1,261

$1,192

Round trip

Unlock all 500+ flight deals to Sydney and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Sydney

For those seeking cheap flights from Chicago to Sydney, fares typically range from $1279–$2139, with a median price of $1642. Right now, current fares are above the typical level for this route. Only 0% of recent fares were classified as a good price, indicating that finding deals can be challenging.

When considering the cheapest time to fly from Chicago to Sydney, May stands out with a median fare of $1002. April also offers more affordable options, with a median fare of $1226. Additionally, December presents a relatively lower median fare of $1508 compared to the overall median.

Most itineraries for flights from Chicago to Sydney involve connections, as 0% of recent fares were non-stop. When connecting, the typical number of stopovers is 2. This means you should expect at least one stop on your journey.

A typical journey from Chicago to Sydney, including connections, takes approximately 53h 19m. This reflects the long-haul nature of the route and the necessity of connecting flights, given the absence of direct options.

The distance between Chicago and Sydney is approximately 14862 km, classifying this as a long-haul route. This significant distance contributes to the extended journey times and the typical need for multiple connections.

How much is a round trip from Chicago to Sydney

Regular price: $1,034 - $1,736

Prices for flights from Chicago to Sydney are currently within the regular range.

The regular price range for flights from Chicago to Sydney is between $1034 and $1736. The current lowest deal is $1104 with Frontier Airlines, for travel from Aug 7-Aug 18.

now $1,104

Low $1,034

High $1,736

The cheapest time to fly from Chicago to Sydney

The cheapest month to fly from Chicago to Sydney is May, with a median price of $1002. The most expensive month is September, with a median price of $2352. Prices are generally lower from April to December.

May

Cheapest

Flights from $1,002

September

Most Expensive

Flights from $2,352

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Nov

Dec

Direct flights from Chicago to Sydney

Frontier Airlines

Fiji Airways

All Nippon Airways

Air Canada

Last-minute flights going from Chicago to Sydney

Tue, Jul 7

⌛ Last-Minute

MDW - Sydney

Chicago (MDW) - Sydney (SYD)

Frontier Airlines, Fiji Airways

$1,425

$1,384

One-way

Tue, Jul 7

⌛ Last-Minute

MDW - Sydney

Chicago (MDW) - Sydney (SYD)

Frontier Airlines, Fiji Airways

$1,425

$1,384

One-way

Tue, Jul 7

⌛ Last-Minute

MDW - Sydney

Chicago (MDW) - Sydney (SYD)

Frontier Airlines, Fiji Airways

$1,411

$1,386

One-way

Fri, Jul 10

⌛ Last-Minute

MDW - Sydney

Chicago (MDW) - Sydney (SYD)

Frontier Airlines

$1,410

$1,250

One-way

Mon, Jul 13

⌛ Last-Minute

ORD - Sydney

Chicago (ORD) - Sydney (SYD)

Frontier Airlines

$1,240

$1,246

One-way

Thu, Jul 16

⌛ Last-Minute

ORD - Sydney

Chicago (ORD) - Sydney (SYD)

Frontier Airlines

$1,254

$1,269

One-way

Biggest price drops on these dates for flights from Chicago to Sydney

14 nights

Jul 10 - Jul 24

$1,410 → $1,250

11%

8 nights

Nov 2 - Nov 10

$1,288 → $1,131

12%

9 nights

Dec 1 - Dec 10

$1,586 → $1,466

13 nights

Dec 1 - Dec 14

$1,609 → $1,489

Popular Airports to fly from Chicago to Sydney

Chicago - Sydney route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Chicago to Sydney are above the typical level at a median of $1642.

📅 Best time to fly

Fly in May for the cheapest prices

Historically, May is the cheapest month to fly from Chicago to Sydney, with a median price of $1002.

⏱️ Flight duration

Expect longer flights with 2+ stops

Flights from Chicago to Sydney typically take 53h 19m, with most routes having 2 or more stops.

✈️ Airlines & availability

Connecting flights only, no direct routes

There are no direct flights available from Chicago to Sydney; all routes include connecting flights.

🏆 Airline highlight

Frontier Airlines offers connecting flights

Frontier Airlines is one of the carriers offering connecting flights from Chicago to Sydney.

🎯 Booking tip

Deals appear regularly for this route

Deals for flights from Chicago to Sydney appear regularly, with about 0.23 deals per day.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to Sydney, with prices starting from $1106.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$1106

Chicago Midway International (MDW)

Chicago Midway International Airport is an alternative departure option for flights to Sydney.

📍 ~15 km from Chicago city center (reachable by car or train).

💸 Flights from ~$1403

Chicago Rockford International (RFD)

Chicago Rockford International Airport is another departure option for flights to Sydney.

📍 ~120 km from Chicago city center (reachable by car).

💸 Flights from ~$1740

Sydney main airports to arrive at

Sydney (SYD)

Cheapest

Sydney Airport is the primary international gateway to Sydney, offering convenient access to the city.

📍 ~8 km from city center (reachable by car)

💸 Flights from ~$1106

Airports nearby Sydney used as alternative

Canberra (CBR)

Cheapest

Canberra Airport can be a useful alternative, offering robust flight schedules and superior infrastructure, despite requiring ground travel from Sydney CBD.

📍 ~240 km from Sydney (reachable by car or rail)

💸 Flights from ~$1039

Newcastle (NTL)

Newcastle Airport is a significant regional alternative with frequent services and easy accessibility from Northern Sydney.

📍 ~135 km from Sydney (reachable by car)

💸 Flights from ~$1209

Coffs Harbour (CFS)

Coffs Harbour Airport is a well-established regional option, though it is a significant distance from Sydney.

📍 ~430 km from Sydney (reachable by car)

💸 Flights from ~$1541

Port Macquarie (PQQ)

Port Macquarie Airport offers reliable regional connectivity, but its long travel distance makes it less practical for Sydney.

📍 ~340 km from Sydney (reachable by car)

💸 Flights from ~$1506

Business & First Class Flight Deals to Sydney

Discover luxury on the budget with premium cabin class on flights from Chicago to Sydney.

Elite

Best Elite deals to Sydney

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Nov 30

Sydney, Australia

90% AI deal score

$7,897

$6,511

Save $1,386

From ORD

Elite

Aug 14

Sydney, Australia

89% AI deal score

$7,687

$6,076

Save $1,611

From ORD

Elite

Aug 14

Sydney, Australia

89% AI deal score

$7,746

$6,108

Save $1,638

From ORD

Elite

Aug 14

Sydney, Australia

89% AI deal score

$7,792

$6,127

Save $1,665

From ORD

Elite

Aug 14

Sydney, Australia

89% AI deal score

$7,697

$6,127

Save $1,570

From ORD

Elite

Aug 14

Sydney, Australia

89% AI deal score

$7,793

$6,220

Save $1,573

From ORD

Elite

Aug 12

Sydney, Australia

89% AI deal score

$7,859

$6,252

Save $1,607

From ORD

Elite

Aug 05

Sydney, Australia

89% AI deal score

$7,805

$6,271

Save $1,534

From ORD

Elite

Aug 05

Sydney, Australia

89% AI deal score

$7,690

$6,271

Save $1,419

From ORD

Elite

Aug 04

Sydney, Australia

89% AI deal score

$7,746

$6,299

Save $1,447

From ORD

Elite

Aug 13

Sydney, Australia

89% AI deal score

$8,000

$6,348

Save $1,652

From ORD

Elite

Aug 29

Sydney, Australia

88% AI deal score

$7,737

$6,285

Save $1,452

From ORD

Elite

Jul 09

Sydney, Australia

84% AI deal score

$7,602

$6,310

Save $1,292

From ORD

Elite

Jul 29

Sydney, Australia

84% AI deal score

$7,644

$6,319

Save $1,325

From ORD

Elite

Jul 30

Sydney, Australia

84% AI deal score

$7,652

$6,327

Save $1,325

From ORD

Elite

Jul 29

Sydney, Australia

84% AI deal score

$7,682

$6,330

Save $1,352

From ORD

Elite

Jul 30

Sydney, Australia

84% AI deal score

$7,689

$6,337

Save $1,352

From ORD

Elite

Aug 13

Sydney, Australia

83% AI deal score

$7,683

$6,389

Save $1,294

From ORD

Elite

Aug 13

Sydney, Australia

81% AI deal score

$7,790

$7,116

Save $674

From ORD

Elite

Oct 03

Sydney, Australia

81% AI deal score

$23,812

$22,074

Save $1,738

From ORD

Elite

Sep 29

Sydney, Australia

81% AI deal score

$24,550

$22,100

Save $2,450

From ORD

Elite

Nov 01

Sydney, Australia

80% AI deal score

$23,288

$22,052

Save $1,236

From ORD

Elite

Oct 11

Sydney, Australia

80% AI deal score

$23,371

$22,100

Save $1,271

From ORD

Elite

Oct 15

Sydney, Australia

80% AI deal score

$23,391

$22,102

Save $1,289

From ORD

Elite

Oct 14

Sydney, Australia

80% AI deal score

$23,416

$22,102

Save $1,314

From ORD

Elite

Aug 20

Sydney, Australia

80% AI deal score

$23,843

$22,818

Save $1,025

From ORD

Elite

Dec 02

Sydney, Australia

79% AI deal score

$22,934

$22,103

Save $831

From ORD

Elite

Dec 02

Sydney, Australia

79% AI deal score

$23,052

$22,325

Save $727

From ORD

Elite

Nov 03

Sydney, Australia

78% AI deal score

$8,033

$7,944

Save $89

From ORD

Elite

Oct 20

Sydney, Australia

78% AI deal score

$24,133

$23,526

Save $607

From ORD

Elite

Sep 10

Sydney, Australia

78% AI deal score

$24,920

$24,364

Save $556

From ORD

Elite

Nov 30

Sydney, Australia

78% AI deal score

$3,464

From ORD

Elite

Nov 02

Sydney, Australia

78% AI deal score

$3,464

From ORD

Elite

Sep 21

Sydney, Australia

78% AI deal score

$3,465

From ORD

Elite

Sep 18

Sydney, Australia

78% AI deal score

$3,513

From ORD

Elite

Oct 11

Sydney, Australia

78% AI deal score

$3,514

From ORD

Elite

Sep 15

Sydney, Australia

78% AI deal score

$3,514

From ORD

Elite

Oct 15

Sydney, Australia

78% AI deal score

$3,514

From ORD

Elite

Oct 01

Sydney, Australia

78% AI deal score

$3,514

From ORD

Elite

Nov 30

Sydney, Australia

78% AI deal score

$3,514

From ORD

Elite

Oct 06

Sydney, Australia

78% AI deal score

$3,514

From ORD

Elite

Nov 29

Sydney, Australia

78% AI deal score

$3,563

From ORD

Elite

Sep 18

Sydney, Australia

78% AI deal score

$3,564

From ORD

Elite

Sep 19

Sydney, Australia

78% AI deal score

$3,564

From ORD

Elite

Nov 04

Sydney, Australia

77% AI deal score

$8,067

$7,989

Save $78

From ORD

Elite

Nov 29

Sydney, Australia

77% AI deal score

$8,059

$8,011

Save $48

From ORD

Elite

Nov 29

Sydney, Australia

77% AI deal score

$8,085

$8,019

Save $66

From ORD

Elite

Nov 29

Sydney, Australia

77% AI deal score

$8,080

$8,019

Save $61

From ORD

Elite

Nov 11

Sydney, Australia

77% AI deal score

$8,023

$8,021

Save $2

From ORD

Elite

Dec 01

Sydney, Australia

77% AI deal score

$8,134

$8,028

Save $106

From ORD

Elite

Aug 03

Sydney, Australia

77% AI deal score

$24,388

From ORD

Elite

Aug 18

Sydney, Australia

77% AI deal score

$3,815

From ORD

Elite

Aug 20

Sydney, Australia

77% AI deal score

$3,815

From ORD

Elite

Aug 05

Sydney, Australia

77% AI deal score

$3,815

From ORD

Elite

Jul 06

Sydney, Australia

77% AI deal score

$3,830

From ORD

Elite

Jul 02

Sydney, Australia

77% AI deal score

$3,830

From ORD

Elite

Aug 13

Sydney, Australia

76% AI deal score

$24,325

From ORD

Elite

Aug 12

Sydney, Australia

76% AI deal score

$24,335

From ORD

Elite

Jun 25

Sydney, Australia

76% AI deal score

$3,830

From ORD

Elite

Dec 01

Sydney, Australia

76% AI deal score

$4,018

From ORD

Elite

Dec 02

Sydney, Australia

76% AI deal score

$4,019

From ORD

Elite

Jun 19

Sydney, Australia

76% AI deal score

$4,029

From ORD

Elite

Dec 01

Sydney, Australia

75% AI deal score

$23,526

From ORD

Elite

Nov 29

Sydney, Australia

75% AI deal score

$4,009

From ORD

Elite

Nov 29

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Nov 01

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Sep 15

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Nov 11

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Nov 02

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Aug 05

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Aug 11

Sydney, Australia

75% AI deal score

$4,018

From ORD

Elite

Sep 28

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Sep 30

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Sep 24

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Sep 24

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Sep 29

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Oct 12

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Sep 29

Sydney, Australia

75% AI deal score

$4,019

From ORD

Elite

Aug 10

Sydney, Australia

74% AI deal score

$3,450

From ORD

Elite

Oct 07

Sydney, Australia

74% AI deal score

$3,451

From ORD

Elite

Aug 25

Sydney, Australia

74% AI deal score

$3,451

From ORD

Elite

Aug 05

Sydney, Australia

74% AI deal score

$3,544

From ORD

Elite

Sep 18

Sydney, Australia

74% AI deal score

$3,662

From ORD

Elite

Nov 01

Sydney, Australia

73% AI deal score

$23,491

From ORD

Elite

Dec 04

Sydney, Australia

73% AI deal score

$23,526

From ORD

Elite

Aug 23

Sydney, Australia

73% AI deal score

$3,440

From ORD

Elite

Aug 24

Sydney, Australia

73% AI deal score

$3,442

From ORD

Elite

Dec 02

Sydney, Australia

73% AI deal score

$3,451

From ORD

Elite

Oct 20

Sydney, Australia

73% AI deal score

$3,547

From ORD

Elite

Aug 07

Sydney, Australia

73% AI deal score

$3,547

From ORD

Elite

Oct 14

Sydney, Australia

73% AI deal score

$3,557

From ORD

Elite

Aug 18

Sydney, Australia

73% AI deal score

$3,557

From ORD

Elite

Oct 24

Sydney, Australia

73% AI deal score

$3,653

From ORD

Elite

Sep 01

Sydney, Australia

72% AI deal score

$8,581

From ORD

Elite

Aug 18

Sydney, Australia

72% AI deal score

$8,581

From ORD

Elite

Jul 21

Sydney, Australia

72% AI deal score

$9,868

From ORD

Elite

Jun 27

Sydney, Australia

72% AI deal score

$10,037

From ORD

Elite

Jul 31

Sydney, Australia

72% AI deal score

$24,325

From ORD

Elite

Oct 20

Sydney, Australia

72% AI deal score

$25,168

From ORD

Elite

Aug 19

Sydney, Australia

71% AI deal score

$9,090

Frequently Asked Questions About Flights to Sydney

Finding affordable flights often involves comparing prices from various airlines and online travel agencies. Consider being flexible with your travel dates and looking into different times of the year. Setting up price alerts can also help you monitor fare changes.

Booking flights in advance can often lead to better deals, especially for long-haul international routes. However, prices can fluctuate, so monitoring fares over time may be beneficial. There isn't a single 'best' time, as it can vary.

Comparing nearby airports can sometimes reveal more economical flight options or different schedules. While it may require additional ground transportation, the savings on airfare can sometimes be significant. It's often worth checking if alternative departure or arrival points are feasible.

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