Cheap Flights from Sydney to Chicago
Browse current best options from Sydney. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Sydney
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
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 Sydney to Chicago
Explore current cheapest deals departing from Sydney to Chicago
Round trip
Sort by: Cheapest
September 9 - September 16
SYD - Chicago
$1,737
$1,024
Round trip
September 7 - September 28
SYD - Chicago
$1,654
$1,024
Round trip
September 3 - September 22
SYD - Chicago
$1,627
$1,025
Round trip
September 7 - September 22
SYD - Chicago
$1,653
$1,025
Round trip
October 7 - October 20
SYD - Chicago
$1,735
$1,025
Round trip
October 5 - October 19
SYD - Chicago
$1,449
$1,027
Round trip
November 16 - November 23
SYD - Chicago
$1,467
$1,027
Round trip
November 16 - November 24
SYD - Chicago
$1,464
$1,027
Round trip
November 16 - November 25
SYD - Chicago
$1,469
$1,027
Round trip
November 16 - November 30
SYD - Chicago
$1,495
$1,027
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Sydney to Chicago
How much is a round trip from Sydney to Chicago
Regular price: $1,421 - $1,908
Prices for flights from Sydney to Chicago are currently below the regular range.
The regular price range for this route is typically between $1421 and $1908. The current lowest deal is $1024 with Deutsche Luft Hansa, for travel from Sep 9-Sep 16.
now $1,024
Low $1,421
High $1,908
The cheapest time to fly from Sydney to Chicago
For flights from Sydney to Chicago, October is the cheapest month with a median price of 1106 USD. The most expensive month to fly is August, with a median price of 1946 USD. Generally, prices are lower from January to November.
October
Flights from $1,106
August
Flights from $1,946
Direct flights from Sydney to Chicago
Deutsche Luft Hansa
Etihad Airways
Jetstar
QantasLink
Last-minute flights going from Sydney to Chicago
Wed, Jul 15
SYD - Chicago
Sydney (SYD) - Chicago (ORD)
QantasLink, Frontier Airlines
$1,385
$1,344
One-way
Thu, Jul 16
SYD - Chicago
Sydney (SYD) - Chicago (ORD)
QantasLink
$1,360
$1,281
One-way
Tue, Jul 21
SYD - Chicago
Sydney (SYD) - Chicago (ORD)
QantasLink, Frontier Airlines
$1,420
$1,350
One-way
Thu, Aug 13
SYD - Chicago
Sydney (SYD) - Chicago (ORD)
Alaska Airlines, Inc.
$1,509
$1,168
One-way
Sat, Aug 15
SYD - Chicago
Sydney (SYD) - Chicago (ORD)
QantasLink
$1,550
$1,077
One-way
Sat, Aug 15
SYD - Chicago
Sydney (SYD) - Chicago (ORD)
QantasLink
$1,498
$1,179
One-way
Biggest price drops on these dates for flights from Sydney to Chicago
Oct 8 - Oct 25
$1,744 → $1,030
41%
Sep 9 - Sep 16
$1,737 → $1,024
41%
Dec 1 - Dec 8
$1,742 → $1,030
41%
Oct 7 - Oct 20
$1,735 → $1,025
41%
Popular Airports to fly from Sydney to Chicago
Sydney - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Sydney to Chicago are below the typical level at $1024.
📅 Best time to fly
October is historically cheapest at $1106
Historically, October is the cheapest month to fly from Sydney to Chicago, with a median price of $1106.
⏱️ Flight duration
Flights typically take 45h 37m
The median flight duration from Sydney to Chicago is 45 hours and 37 minutes, with 3 stopovers.
✈️ Airlines & availability
Connecting flights are typical for this route
This route is connecting dominant, with frequent deals available from various providers.
🏆 Airline highlight
Deutsche Luft Hansa offers deals from $1024
Deutsche Luft Hansa recently offered a deal for $1024 from Sydney to Chicago.
🎯 Booking tip
Deals appear frequently
Deals for flights from Sydney to Chicago appear frequently, about 0.53 deals per day.
Sydney main airports to depart from
Sydney (SYD)
Sydney Airport is a convenient departure point for flights to Chicago.
📍 ~10 km from city center (reachable by car or train)
💸 Flights from ~$1024
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a good option for flights from Sydney to Chicago, offering the cheapest flights.
📍 ~15 km from Chicago city center (reachable by car)
💸 Flights from ~$1024
Chicago Rockford International (RFD)
Chicago Rockford International serves the Chicago area for flights from Sydney.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$1881
O Hare International (ORD)
O Hare International is a convenient arrival airport for flights from Sydney to Chicago.
📍 ~25 km from Chicago city center (reachable by car)
💸 Flights from ~$1025
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
Consider MKE for excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$1302
South Bend International (SBN)
SBN is geographically the closest alternative to Chicago, with direct commuter rail connections to downtown.
📍 ~130 km from Chicago (reachable by car or train)
💸 Flights from ~$1068
Gerald R. Ford International (GRR)
GRR is a major regional hub offering a wide range of cabin classes for travelers on Chicago's eastern side.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$1076
Dane County Regional (MSN)
MSN is a reliable regional airport with consistent service and less congestion than major Chicago hubs.
📍 ~210 km from Chicago (reachable by car)
💸 Flights from ~$1217
Fort Wayne International (FWA)
FWA offers stable regional service and is an alternative for travelers in Chicago's southeastern suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$1019
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Sydney to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From SYD
Elite
Jul 25
Chicago, United States
93% AI deal score
$8,182
$5,251
Save $2,931
From SYD
Elite
Jul 29
Chicago, United States
91% AI deal score
$8,344
$5,843
Save $2,501
From SYD
Elite
Aug 12
Chicago, United States
91% AI deal score
$8,622
$6,154
Save $2,468
From SYD
Elite
Aug 06
Chicago, United States
91% AI deal score
$8,475
$6,189
Save $2,286
From SYD
Elite
Aug 07
Chicago, United States
91% AI deal score
$8,480
$6,198
Save $2,282
From SYD
Elite
Aug 02
Chicago, United States
91% AI deal score
$8,683
$6,198
Save $2,485
From SYD
Elite
Jun 19
Chicago, United States
91% AI deal score
$31,376
$22,540
Save $8,836
From SYD
Elite
Aug 10
Chicago, United States
90% AI deal score
$8,781
$6,044
Save $2,737
From SYD
Elite
Aug 07
Chicago, United States
90% AI deal score
$8,566
$6,055
Save $2,511
From SYD
Elite
Aug 09
Chicago, United States
90% AI deal score
$8,654
$6,136
Save $2,518
From SYD
Elite
Jul 23
Chicago, United States
90% AI deal score
$8,129
$6,189
Save $1,940
From SYD
Elite
Nov 29
Chicago, United States
90% AI deal score
$7,775
$6,227
Save $1,548
From SYD
Elite
Aug 10
Chicago, United States
90% AI deal score
$9,095
$6,256
Save $2,839
From SYD
Elite
Aug 07
Chicago, United States
90% AI deal score
$8,899
$6,267
Save $2,632
From SYD
Elite
Aug 10
Chicago, United States
90% AI deal score
$8,899
$6,353
Save $2,546
From SYD
Elite
Aug 10
Chicago, United States
89% AI deal score
$8,077
$6,254
Save $1,823
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,077
$6,264
Save $1,813
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,654
$6,267
Save $2,387
From SYD
Elite
Aug 10
Chicago, United States
89% AI deal score
$8,501
$6,278
Save $2,223
From SYD
Elite
Aug 10
Chicago, United States
89% AI deal score
$8,512
$6,279
Save $2,233
From SYD
Elite
Aug 10
Chicago, United States
89% AI deal score
$8,410
$6,279
Save $2,131
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,475
$6,289
Save $2,186
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,390
$6,290
Save $2,100
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,498
$6,290
Save $2,208
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,512
$6,317
Save $2,195
From SYD
Elite
Aug 07
Chicago, United States
89% AI deal score
$8,580
$6,363
Save $2,217
From SYD
Elite
Aug 07
Chicago, United States
88% AI deal score
$8,077
$6,290
Save $1,787
From SYD
Elite
Jul 22
Chicago, United States
84% AI deal score
$8,155
$6,569
Save $1,586
From SYD
Elite
Nov 28
Chicago, United States
84% AI deal score
$7,775
$6,646
Save $1,129
From SYD
Elite
Jul 29
Chicago, United States
83% AI deal score
$8,171
$6,808
Save $1,363
From SYD
Elite
Jul 27
Chicago, United States
81% AI deal score
$3,139
$2,930
Save $209
From SYD
Elite
Jul 19
Chicago, United States
81% AI deal score
$3,144
$2,965
Save $179
From SYD
Elite
Jul 25
Chicago, United States
81% AI deal score
$3,242
$3,064
Save $178
From SYD
Elite
Jul 14
Chicago, United States
79% AI deal score
$3,143
$3,042
Save $101
From SYD
Elite
Jul 15
Chicago, United States
79% AI deal score
$3,144
$3,042
Save $102
From SYD
Elite
Jul 17
Chicago, United States
79% AI deal score
$3,145
$3,077
Save $68
From SYD
Elite
Oct 13
Chicago, United States
78% AI deal score
$2,966
$2,926
Save $40
From SYD
Elite
Oct 27
Chicago, United States
78% AI deal score
$2,966
$2,930
Save $36
From SYD
Elite
Nov 02
Chicago, United States
78% AI deal score
$2,982
$2,930
Save $52
From SYD
Elite
Oct 26
Chicago, United States
78% AI deal score
$2,972
$2,930
Save $42
From SYD
Elite
Oct 22
Chicago, United States
78% AI deal score
$2,967
$2,930
Save $37
From SYD
Elite
Nov 04
Chicago, United States
78% AI deal score
$2,982
$2,930
Save $52
From SYD
Elite
Aug 06
Chicago, United States
78% AI deal score
$2,936
$2,930
Save $6
From SYD
Elite
Aug 04
Chicago, United States
78% AI deal score
$2,931
$2,930
Save $1
From SYD
Elite
Oct 04
Chicago, United States
78% AI deal score
$2,979
$2,958
Save $21
From SYD
Elite
Oct 17
Chicago, United States
78% AI deal score
$2,967
$2,965
Save $2
From SYD
Elite
Oct 04
Chicago, United States
78% AI deal score
$2,985
$2,965
Save $20
From SYD
Elite
Oct 30
Chicago, United States
78% AI deal score
$2,970
$2,965
Save $5
From SYD
Elite
Nov 07
Chicago, United States
78% AI deal score
$2,980
$2,965
Save $15
From SYD
Elite
Nov 13
Chicago, United States
78% AI deal score
$2,979
$2,965
Save $14
From SYD
Elite
Sep 13
Chicago, United States
78% AI deal score
$3,079
$3,077
Save $2
From SYD
Elite
Jul 23
Chicago, United States
77% AI deal score
$24,966
$24,004
Save $962
From SYD
Elite
Jun 21
Chicago, United States
77% AI deal score
$27,665
$27,663
Save $2
From SYD
Elite
Sep 15
Chicago, United States
77% AI deal score
$3,122
From SYD
Elite
Jun 18
Chicago, United States
77% AI deal score
$3,158
From SYD
Elite
Nov 17
Chicago, United States
77% AI deal score
$3,287
From SYD
Elite
Nov 15
Chicago, United States
77% AI deal score
$3,290
From SYD
Elite
Aug 02
Chicago, United States
77% AI deal score
$3,403
From SYD
Elite
Sep 18
Chicago, United States
77% AI deal score
$3,490
From SYD
Elite
Aug 17
Chicago, United States
76% AI deal score
$8,563
From SYD
Elite
Jun 28
Chicago, United States
76% AI deal score
$3,314
From SYD
Elite
Jun 23
Chicago, United States
76% AI deal score
$3,396
From SYD
Elite
Aug 06
Chicago, United States
76% AI deal score
$3,652
From SYD
Elite
Sep 01
Chicago, United States
76% AI deal score
$3,803
From SYD
Elite
Jul 20
Chicago, United States
75% AI deal score
$3,640
From SYD
Elite
Jul 21
Chicago, United States
75% AI deal score
$3,652
From SYD
Elite
Aug 10
Chicago, United States
74% AI deal score
$8,563
From SYD
Elite
Jul 20
Chicago, United States
74% AI deal score
$3,640
From SYD
Elite
Jul 21
Chicago, United States
74% AI deal score
$3,652
From SYD
Elite
Jul 21
Chicago, United States
74% AI deal score
$3,652
From SYD
Elite
Jul 17
Chicago, United States
74% AI deal score
$3,673
From SYD
Elite
Jul 20
Chicago, United States
74% AI deal score
$3,699
From SYD
Elite
Jul 20
Chicago, United States
74% AI deal score
$3,699
From SYD
Elite
Jul 21
Chicago, United States
74% AI deal score
$3,711
From SYD
Elite
Jul 21
Chicago, United States
74% AI deal score
$3,711
From SYD
Elite
Jul 22
Chicago, United States
74% AI deal score
$3,784
From SYD
Elite
Aug 17
Chicago, United States
74% AI deal score
$4,146
From SYD
Elite
Aug 25
Chicago, United States
74% AI deal score
$4,146
From SYD
Elite
Aug 05
Chicago, United States
74% AI deal score
$4,146
From SYD
Elite
Aug 25
Chicago, United States
73% AI deal score
$4,146
From SYD
Elite
Oct 15
Chicago, United States
73% AI deal score
$4,253
From SYD
Elite
Oct 05
Chicago, United States
73% AI deal score
$4,253
From SYD
Elite
Oct 21
Chicago, United States
73% AI deal score
$4,254
From SYD
Elite
Sep 28
Chicago, United States
73% AI deal score
$4,254
From SYD
Elite
Oct 09
Chicago, United States
73% AI deal score
$4,359
From SYD
Elite
Sep 15
Chicago, United States
73% AI deal score
$4,707
From SYD
Elite
Sep 28
Chicago, United States
71% AI deal score
$9,187
From SYD
Elite
Jul 05
Chicago, United States
71% AI deal score
$27,513
From SYD
Elite
Oct 24
Chicago, United States
71% AI deal score
$5,047
From SYD
Elite
Aug 02
Chicago, United States
70% AI deal score
$10,230
From SYD
Elite
Aug 02
Chicago, United States
70% AI deal score
$10,230
From SYD
Elite
Jul 18
Chicago, United States
70% AI deal score
$10,242
From SYD
Elite
Jul 08
Chicago, United States
70% AI deal score
$11,472
From SYD
Elite
Jul 21
Chicago, United States
70% AI deal score
$11,641
From SYD
Elite
Jul 09
Chicago, United States
70% AI deal score
$33,371
From SYD
Elite
Jul 10
Chicago, United States
70% AI deal score
$33,476
From SYD
Elite
Jul 08
Chicago, United States
70% AI deal score
$33,919
From SYD
Elite
Aug 04
Chicago, United States
70% AI deal score
$35,734
From SYD
Elite
Jul 20
Chicago, United States
70% AI deal score
$4,146
From SYD
Elite
Jul 01
Chicago, United States
70% AI deal score
$4,146