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S$ 794+ Cheap flights to Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28-1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
17 Dec — 24 Dec1
1 adult

Find flights to Chicago within your budget

Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 216,420 searches and data was last updated on 12 December 2024.

Fly from

Any airport

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 2-2

22:30-08:40

1 stop24h 10m

Chicago O'Hare Intl

Mon 17-2

11:25-20:25

1 stop43h 00m

S$ 1,253

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 12-2

23:25-10:10

1 stop24h 45m

Chicago O'Hare Intl

Thu 20-2

20:30-17:35

1 stop31h 05m

S$ 1,288

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 22-1

11:00-09:39

2 stops36h 39m

Chicago Midway

Sun 2-2

18:59-00:10

2 stops39h 11m

S$ 1,324

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 11-2

11:00-09:55

2 stops36h 55m

Chicago O'Hare Intl

Wed 19-2

06:15-05:00

2 stops32h 45m

S$ 1,324

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 11-2

01:25-13:00

1 stop25h 35m

Chicago O'Hare Intl

Thu 20-2

14:40-16:20

2 stops35h 40m

S$ 1,331

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 22-1

10:10-19:59

1 stop23h 49m

Chicago O'Hare Intl

Sun 2-2

08:55-08:00

1 stop33h 05m

S$ 1,334

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 28-3

09:30-07:30

1 stop35h 00m

Chicago O'Hare Intl

Fri 11-4

12:00-08:10

1 stop31h 10m

S$ 1,428

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 20-1

02:20-07:35

1 stop19h 15m

Chicago O'Hare Intl

Sun 26-1

10:35-17:25

1 stop40h 50m

S$ 1,473

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 18-3

15:45-20:35

1 stop41h 50m

Chicago O'Hare Intl

Sat 22-3

00:30-14:30

1 stop25h 00m

S$ 1,480

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 1-2

02:20-13:49

2 stops25h 29m

Chicago O'Hare Intl

Mon 17-2

10:35-06:40

1 stop30h 05m

S$ 1,503

Flights are sorted by cheapest return flights first.

Deals found on 12-12

Showing 1-10 of 41 results
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Flights to Chicago in 2024

Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 216,420 searches and data was last updated on 12 December 2024.

Return from

S$ 1,253

One-way from

S$ 794

Popular in

August

Cheapest in

October

Average price

S$ 1,616
Korean Air
  • Korean Air
  • 2-2-17-2
  • 2 total stops
  • 67h 10m total
  • Singapore to Chicago
Search Deals
28-1
  • 28-1
  • 2 total stops
  • 52h 08m total
  • Singapore to Chicago
Search Deals
High demand for flights, 5% potential price rise
Search Deals
Best time to find cheap flights, 1% potential price drop
Search Deals
Average for return flights in December 2024
Search Deals

Find flight deals to Chicago

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 12 December 2024.

Tue 17-1208:20SIN - ORD
1 stop36h 10mAir India
Sat 28-1211:00ORD - SIN
1 stop30h 00mAir India
Deal found 11-12S$ 1,634
Mon 30-1200:05SIN - ORD
1 stop30h 10mMultiple Airlines
Sun 20-421:25ORD - SIN
1 stop30h 10mMultiple Airlines
Deal found 12-12S$ 1,755
Mon 30-1200:05SIN - ORD
1 stop30h 10mSWISS
Sat 8-319:05ORD - SIN
1 stop32h 50mSWISS
Deal found 11-12S$ 1,757
Tue 31-1206:35SIN - ORD
1 stop22h 30mUnited Airlines
Mon 21-416:09ORD - SIN
1 stop25h 36mUnited Airlines
Deal found 11-12S$ 1,761
Tue 31-1213:15SIN - ORD
1 stop20h 20mEVA Air
Fri 25-400:30ORD - SIN
1 stop24h 20mEVA Air
Deal found 11-12S$ 1,765
Mon 16-1201:25SIN - ORD
1 stop25h 35mCathay Pacific
Sat 28-1214:40ORD - SIN
1 stop43h 45mCathay Pacific
Deal found 11-12S$ 1,824
Tue 31-1210:00SIN - ORD
2 stops23h 55mAir Canada
Wed 5-315:40ORD - SIN
1 stop26h 15mAir Canada
Deal found 11-12S$ 1,856
Tue 31-1208:15SIN - ORD
2 stops25h 24mJapan Airlines
Wed 23-412:05ORD - SIN
1 stop29h 10mJapan Airlines
Deal found 12-12S$ 1,914
Tue 31-1211:00SIN - ORD
2 stops26h 59mDelta
Sat 26-412:20ORD - SIN
1 stop22h 20mDelta
Deal found 11-12S$ 1,930
Tue 31-1201:30SIN - ORD
1 stop21h 10mKorean Air
Sat 26-412:20ORD - SIN
1 stop27h 40mKorean Air
Deal found 12-12S$ 2,262
Tue 31-1206:35SIN - ORD
1 stop21h 15mANA
Mon 21-407:00ORD - SIN
2 stops28h 45mANA
Deal found 11-12S$ 2,388
Tue 31-1223:55SIN - ORD
2 stops34h 04mAir China
Tue 4-308:45ORD - SIN
3 stops47h 10mAir China
Deal found 11-12S$ 4,436

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight from Singapore to Chicago. Price data was last updated on 6 December 2024.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.