Cheap flights to Chicago – Compare and Save

— CHI
1 May — 8 May1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 1 April 2026.

Return from

$1,493

One-way from

$736

Popular in

December

Cheapest in

August

Average price

$1,841
21/4-6/5
  • 21/4-6/5
  • 6 total stops
  • 67h 57m total
  • Sydney to Chicago
Search Deals
19/8
  • 19/8
  • 3 total stops
  • 42h 14m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($73 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($23 potential savings vs. average return price).
Search Deals
Average for return flights in April 2026
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Find flight deals to Chicago

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Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 1 April 2026.

Tue 21/413:15
SYD
-
ORD
3 stops35h 47m
Multiple Airlines
Wed 6/512:40
ORD
-
SYD
3 stops32h 10m
Multiple Airlines
Deal found 1/4$1,493
Tue 19/513:15
SYD
-
MDW
3 stops36h 54m
Multiple Airlines
Tue 26/506:00
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Deal found 31/3$1,606
Tue 12/513:15
SYD
-
ORD
3 stops48h 58m
Multiple Airlines
Tue 19/506:55
ORD
-
SYD
3 stops37h 55m
Multiple Airlines
Deal found 28/3$1,661
Fri 17/406:00
SYD
-
ORD
2 stops32h 27m
Multiple Airlines
Sat 2/508:00
ORD
-
SYD
2 stops36h 50m
Multiple Airlines
Deal found 28/3$1,705
Mon 27/413:15
SYD
-
ORD
2 stops25h 12m
Multiple Airlines
Sun 3/505:15
ORD
-
SYD
2 stops39h 35m
Multiple Airlines
Deal found 29/3$1,711
Tue 19/517:50
SYD
-
ORD
1 stop27h 49m
Multiple Airlines
Tue 26/520:46
ORD
-
SYD
1 stop43h 44m
Multiple Airlines
Deal found 31/3$1,718
Tue 12/513:15
SYD
-
MDW
3 stops36h 54m
Multiple Airlines
Tue 19/506:00
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Deal found 28/3$1,720
Mon 27/417:50
SYD
-
ORD
1 stop27h 00m
Multiple Airlines
Sun 3/505:15
ORD
-
SYD
2 stops39h 35m
Multiple Airlines
Deal found 29/3$1,726
Tue 19/517:50
SYD
-
ORD
1 stop27h 49m
Multiple Airlines
Sat 30/509:30
ORD
-
SYD
2 stops35h 20m
Multiple Airlines
Deal found 29/3$1,734
Tue 12/517:50
SYD
-
ORD
1 stop27h 49m
Multiple Airlines
Tue 19/512:40
ORD
-
SYD
2 stops32h 10m
Multiple Airlines
Deal found 28/3$1,737
Fri 15/513:15
SYD
-
MDW
3 stops36h 49m
Multiple Airlines
Fri 22/506:00
MDW
-
SYD
3 stops38h 50m
Multiple Airlines
Deal found 31/3$1,743
Tue 19/517:50
SYD
-
ORD
1 stop27h 49m
Multiple Airlines
Tue 26/508:00
ORD
-
SYD
2 stops36h 50m
Multiple Airlines
Deal found 29/3$1,744

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