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Cheap flights from Singapore to Chicago from S$ 655

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 22-2. Fares are subject to change and may not be available on all flights or dates of travel.
SIN — CHI
8 Feb — 15 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Singapore to Chicago

Keep the following information in mind while searching for Singapore to Chicago flight deals. Data was last updated 9 January 2026.

Round-trip from

S$ 1,135

One-way from

S$ 655

Popular in

January

Cheapest in

September

Average price

S$ 1,595
IndiGo
  • IndiGo
  • 5-2-12-2
  • 4 total stops
  • 84h 40m total
  • Singapore to Chicago
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22-2
  • 22-2
  • 2 total stops
  • 48h 20m total
  • Singapore to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (S$ 72 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (S$ 28 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 2026
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Find flight deals from Singapore to Chicago

Enter your travel dates to find the best prices.

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 9 January 2026.

Thu 5-219:40SIN - ORD
2 stops36h 45mIndiGo
Thu 12-220:20ORD - SIN
2 stops47h 55mIndiGo
Deal found 8-1S$ 1,135
Thu 22-108:50SIN - ORD
1 stop19h 51mAir Canada
Wed 4-215:35ORD - SIN
1 stop25h 25mAir Canada
Deal found 6-1S$ 1,151
Thu 19-214:25SIN - ORD
2 stops35h 36mMultiple Airlines
Thu 26-213:00ORD - SIN
2 stops34h 05mMultiple Airlines
Deal found 6-1S$ 1,157
Mon 22-613:45SIN - ORD
2 stops29h 35mMultiple Airlines
Tue 7-719:40ORD - SIN
2 stops27h 55mMultiple Airlines
Deal found 6-1S$ 1,158
Thu 22-114:25SIN - ORD
2 stops40h 45mMultiple Airlines
Mon 2-208:00ORD - SIN
2 stops39h 05mMultiple Airlines
Deal found 6-1S$ 1,185
Wed 22-407:30SIN - ORD
1 stop39h 10mKorean Air
Sun 26-412:20ORD - SIN
1 stop27h 40mKorean Air
Deal found 6-1S$ 1,188
Thu 22-122:25SIN - ORD
1 stop23h 10mJapan Airlines
Mon 2-217:40ORD - SIN
1 stop22h 55mJapan Airlines
Deal found 6-1S$ 1,194
Tue 17-210:10SIN - ORD
1 stop33h 02mUnited Airlines
Wed 18-209:01ORD - SIN
1 stop32h 59mUnited Airlines
Deal found 5-1S$ 1,200
Fri 20-222:30SIN - ORD
1 stop24h 10mKorean Air
Fri 27-211:25ORD - SIN
1 stop27h 35mKorean Air
Deal found 6-1S$ 1,202
Sat 31-102:20SIN - ORD
1 stop19h 15mJapan Airlines
Fri 6-210:35ORD - SIN
1 stop24h 15mJapan Airlines
Deal found 8-1S$ 1,203
Sun 22-222:30SIN - MDW
2 stops38h 01mDelta
Sun 1-318:20MDW - SIN
2 stops39h 50mDelta
Deal found 7-1S$ 1,241
Thu 19-214:25SIN - MDW
2 stops37h 05mMultiple Airlines
Thu 26-211:00MDW - SIN
2 stops36h 05mMultiple Airlines
Deal found 6-1S$ 1,377

Cheapflights Fare Finder

 
Customise 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 200,618 searches. Data last updated 9 January 2026.
Use the filters below to find and compare flights from Singapore to Chicago that are best for you.

Fly from

Singapore

Fly to

Chicago

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 22-1

14:25-17:10

2 stops40h 45m

Chicago O'Hare Intl

Mon 2-2

08:00-13:05

2 stops39h 05m

S$ 1,185

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 22-1

22:25-07:35

1 stop23h 10m

Chicago O'Hare Intl

Mon 2-2

17:40-06:35

1 stop22h 55m

S$ 1,194

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 20-2

10:40-08:40

1 stop36h 00m

Chicago O'Hare Intl

Fri 27-2

11:25-00:10

1 stop22h 45m

S$ 1,200

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 17-2

22:20-06:19

1 stop21h 59m

Chicago O'Hare Intl

Wed 18-2

09:01-08:00

1 stop32h 59m

S$ 1,203

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 31-1

02:20-07:35

1 stop19h 15m

Chicago O'Hare Intl

Fri 6-2

10:35-00:50

1 stop24h 15m

S$ 1,203

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 23-1

22:20-05:44

1 stop21h 24m

Chicago O'Hare Intl

Sat 14-2

18:17-20:15

1 stop35h 58m

S$ 1,207

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 24-6

20:40-04:58

1 stop21h 18m

Chicago O'Hare Intl

Thu 9-7

21:39-18:35

1 stop31h 56m

S$ 1,210

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 22-2

22:20-06:19

1 stop21h 59m

Chicago O'Hare Intl

Sun 1-3

12:46-20:15

1 stop41h 29m

S$ 1,210

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 3-6

08:45-05:57

1 stop34h 12m

Chicago O'Hare Intl

Thu 6-8

06:02-18:35

1 stop23h 33m

S$ 1,210

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 21-3

10:10-00:59

1 stop27h 49m

Chicago O'Hare Intl

Wed 25-3

14:26-07:00

1 stop27h 34m

S$ 1,210

Flights are sorted by cheapest return flights first.

Deals found on 8-1

Showing 1-10 of 41 results
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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 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.

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 S$ 893). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,473). 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 9 January 2026.
Read reviews from past customers who have flown with EVA Air, ANA, andCathay Pacific from Singapore to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very Good
1,314 reviews
Check prices

Boarding

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Jan 2026

CGK - TPE

I had lots of room on the exit row. Boarding was quick and easy.
EVA Air
8.4
Very Good
1,314 reviews
EVA Air
8.4
Very Good
1,314 reviews
Check prices

Boarding

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Jan 2026

CGK - TPE

I had lots of room on the exit row. Boarding was quick and easy.
ANA
8.4
Very Good
1,063 reviews
EVA Air
8.4
Very Good
1,314 reviews
Check prices

Boarding

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Jan 2026

CGK - TPE

I had lots of room on the exit row. Boarding was quick and easy.
Cathay Pacific
7.6
Good
1,126 reviews
EVA Air
8.4
Very Good
1,314 reviews
Check prices

Boarding

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Jan 2026

CGK - TPE

I had lots of room on the exit row. Boarding was quick and easy.
United Airlines
7.4
Good
9,143 reviews
EVA Air
8.4
Very Good
1,314 reviews
Check prices

Boarding

8.4

Crew

8.6

Food

8.1

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Jan 2026

CGK - TPE

I had lots of room on the exit row. Boarding was quick and easy.

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?

    Japan Airlines, Korean Air, and United Airlines can get you from Singapore to Chicago in just under 21h 59m. Your travel time can differ by up to 14h 01m. The distance between Singapore and Chicago is about 15039 km. This flight may include one or multiple stops.

  • 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 holiday 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 S$ 893). Flying from Singapore to Chicago in January is currently the most expensive (average of S$ 1,473). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Singapore to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Singapore to O'Hare Intl flights
Singapore to Midway flights

Top 4 airlines flying from Singapore to Chicago

Discover the top 4 airlines 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 200,618 searches. Data last updated 9 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestS$ 886AverageS$ 1,328FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Japan AirlinesCheapestS$ 892AverageS$ 1,541FlexibilityNo cancel feeOn-time79%
Search Japan Airlines flights
ANACheapestS$ 1,056AverageS$ 2,828FlexibilityNo cancel feeOn-time80%
Search ANA flights
EVA AirCheapestS$ 1,300AverageS$ 1,508FlexibilityNo cancel feeOn-time74%
Search EVA Air flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Singapore to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Singapore today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Singapore to Chicago?

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Can Cheapflights find flights from Singapore to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Singapore to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Singapore to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Singapore to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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