Chicago

$506+ Cheap flights from Singapore to Chicago (CHI)

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
Apr 5 — Apr 121
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Cheap flight deals from Singapore to Chicago

Cheapest flights from Singapore to Chicago
Explore the most affordable flight options available from Singapore to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 6, 2026.

This FlightHub deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:05 am
SIN
-
ORD
1 stop34h 35m
ANA
Sun 11/84:25 pm
ORD
-
SIN
1 stop24h 30m
ANA
Deal found 3/4$828
This ANA deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure ANA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:05 am
SIN
-
ORD
2 stops25h 15m
Multiple Airlines
Sun 11/84:25 pm
ORD
-
SIN
1 stop24h 30m
Multiple Airlines
Deal found 3/4$861
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:00 am
SIN
-
ORD
1 stop35h 07m
United Airlines
Mon 4/66:25 am
ORD
-
SIN
1 stop23h 10m
United Airlines
Deal found 3/3$945
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:35 pm
SIN
-
ORD
1 stop23h 41m
United Airlines
Wed 7/156:10 am
ORD
-
SIN
1 stop23h 25m
United Airlines
Deal found 3/4$946
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:10 am
SIN
-
ORD
1 stop21h 42m
United Airlines
Wed 4/13:45 pm
ORD
-
SIN
1 stop26h 00m
United Airlines
Deal found 3/3$948
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:20 pm
SIN
-
ORD
1 stop20h 57m
United Airlines
Fri 5/16:20 am
ORD
-
SIN
1 stop23h 15m
United Airlines
Deal found 3/2$949
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1010:10 am
SIN
-
ORD
1 stop24h 27m
United Airlines
Wed 4/12:15 pm
ORD
-
SIN
1 stop27h 30m
United Airlines
Deal found 3/2$954
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:00 am
SIN
-
ORD
1 stop27h 29m
United Airlines
Thu 4/239:40 pm
ORD
-
SIN
1 stop31h 55m
United Airlines
Deal found 3/1$955
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:00 am
SIN
-
ORD
1 stop24h 18m
United Airlines
Wed 4/154:40 pm
ORD
-
SIN
1 stop25h 05m
United Airlines
Deal found 3/4$958
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:00 pm
SIN
-
MDW
2 stops27h 33m
Delta
Sun 11/85:59 pm
MDW
-
SIN
2 stops40h 11m
Delta
Deal found 3/4$959
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:30 am
SIN
-
ORD
2 stops26h 48m
Delta
Tue 4/217:09 pm
ORD
-
SIN
2 stops39h 46m
Delta
Deal found 3/4$959
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:30 am
SIN
-
ORD
2 stops29h 28m
Delta
Sun 4/267:15 am
ORD
-
SIN
2 stops27h 40m
Delta
Deal found 3/5$960

Find flight deals from Singapore to Chicago

Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated March 6, 2026.

Round-trip from

$945
(United Airlines)

One-way from

$506
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$1,076
From Singapore to Chicago (CHI)
One-way flight from Singapore to Chicago (CHI)
Highest demand for flights based on searches. 3% potential increase in price ($36 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($34 potential savings vs. average RT price).
Average for round-trip flights in March 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Singapore to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 6, 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 4/2

9:00 am-7:07 am

1 stop35h 07m

Chicago O'Hare Intl

Mon 4/6

6:25 am-6:35 pm

1 stop23h 10m

$945
Quickest round-trip

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 6/25

8:35 pm-7:16 am

1 stop23h 41m

Chicago O'Hare Intl

Wed 7/15

6:10 am-6:35 pm

1 stop23h 25m

$946

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 3/19

10:10 am-6:52 pm

1 stop21h 42m

Chicago O'Hare Intl

Wed 4/1

3:45 pm-6:45 am

1 stop26h 00m

$948

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 6/17

8:45 am-6:35 pm

1 stop22h 50m

Chicago O'Hare Intl

Sat 7/4

9:33 pm-6:15 am

1 stop43h 42m

$949

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 5/2

8:35 pm-5:25 am

1 stop21h 50m

Chicago O'Hare Intl

Fri 5/8

6:20 pm-6:35 pm

1 stop35h 15m

$949

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 4/16

9:00 am-11:29 pm

1 stop27h 29m

Chicago O'Hare Intl

Thu 4/23

9:40 pm-6:35 pm

1 stop31h 55m

$955

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 4/14

1:25 am-9:18 pm

2 stops32h 53m

Chicago O'Hare Intl

Wed 4/22

5:15 am-11:55 pm

2 stops29h 40m

$969

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 4/22

10:00 pm-4:26 pm

2 stops31h 26m

Chicago Midway

Sun 4/26

9:27 am-11:55 pm

2 stops25h 28m

$1,069

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 4/15

10:00 pm-12:07 pm

2 stops27h 07m

Chicago Midway

Wed 4/22

9:29 am-11:55 pm

2 stops25h 26m

$1,079

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Fri 4/17

1:45 pm-5:40 am

2 stops28h 55m

Chicago Midway

Fri 4/24

11:00 am-12:35 pm

2 stops36h 35m

$1,082

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 38 resultsSorted by cheapest first
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Best time to book a flight from Singapore to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Singapore with our price prediction graph.
Estimated round-trip 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.

Cheapflights Insights

Everything you need to know about your flight from Singapore to Chicago

What is the cheapest month to book a flight from Singapore to Chicago?

Currently, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of $695). Flying from Singapore to Chicago in January is currently the most expensive (average of $1,200). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated March 6, 2026.
Read through reviews of airlines operating flights from Singapore to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

7.7

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Boarding

7.7

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Related info for your journey

Find useful and relevant information for your journey from Singapore to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Singapore to Chicago?

    There are many flights that can get you from Singapore to Chicago in 31h 26m. Fly via United Airlines or Delta to get the fastest option. The distance from Singapore to Chicago is about 9360 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Singapore to Chicago one-way?

    To fly one-way, consider booking your trip with Japan Airlines, which is currently one of the cheapest options available, starting at $428. EVA Air flights start at $442 while deals on United Airlines start at $577 one-way.

  • Can I find deals for flights from Singapore to Chicago that include hotel bookings?

    Yes. In addition to deals on Singapore to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Singapore to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Singapore to Chicago.

  • Can I find deals for business class flights from Singapore to Chicago?

    Yes. Cheapflights offers flight deals from Singapore to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Singapore to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Singapore to Chicago (average of $695). Flying from Singapore to Chicago in January is currently the most expensive (average of $1,200). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Singapore to Chicago

Discover the top airline that operate flights from Singapore to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$802Average$1,040FlexibilityNo cancel feeOn-time69%

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