SIN - CHI

S$ 625 Find Cheap Flights from Singapore to Chicago – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Singapore to Chicago departing on 15-10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest return fare
S$ 987
Typical prices: S$ 1,098-S$ 1,418
Air Canada
Tue 8-9Tue 15-9
SIN - ORD • 2 stops
Cheapest one-way flight
S$ 625
Typical prices: S$ 821-S$ 893
Air Canada
Thu 15-10
SIN - ORD • 1 stop
Top airlines
Cheapest • from S$ 987 (return)
Best reviews • 8.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Singapore and Chicago. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top stopover airports
Cheapest • Avg S$ 1,073 (return)
Shortest trip • 20h 44m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Singapore to Chicago (SIN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Singapore to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Singapore to Chicago

Tue, 8 Sep - Tue, 15 Sep
Air Canada Logo
06:15 - 20:12
SIN
-
ORD
26h 57m
2 stops
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 987Air Canada
Thu, 24 Sep - Sun, 27 Sep
Air Canada Logo
07:00 - 14:43
SIN
-
ORD
20h 43m
1 stop
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 1,001Air Canada
Tue, 8 Sep - Tue, 15 Sep
Air Canada Logo
06:15 - 20:12
SIN
-
ORD
26h 57m
2 stops
Air Canada Logo
09:55 - 00:45
ORD
-
SIN
25h 50m
2 stops
S$ 1,004Air Canada
Thu, 10 Sep - Thu, 24 Sep
Air Canada Logo
07:00 - 14:43
SIN
-
ORD
20h 43m
1 stop
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 1,009Air Canada
Thu, 10 Sep - Thu, 24 Sep
Air Canada Logo
20:50 - 14:43
SIN
-
ORD
30h 53m
2 stops
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 1,012Air Canada
Thu, 10 Sep - Thu, 24 Sep
Air Canada Logo
20:50 - 14:43
SIN
-
ORD
30h 53m
2 stops
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 1,013Air Canada
Thu, 10 Sep - Thu, 24 Sep
Air Canada Logo
07:00 - 14:43
SIN
-
ORD
20h 43m
1 stop
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 1,014Air Canada
Thu, 10 Sep - Thu, 24 Sep
Air Canada Logo
20:50 - 14:43
SIN
-
ORD
30h 53m
2 stops
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
24h 35m
1 stop
S$ 1,014Air Canada
Sat, 5 Sep - Sat, 5 Sep
United Airlines Logo
08:45 - 18:35
SIN
-
ORD
22h 50m
1 stop
United Airlines Logo
21:40 - 18:35
ORD
-
SIN
31h 55m
1 stop
S$ 1,414United Airlines
Wed, 9 Sep - Wed, 16 Sep
United Airlines Logo
20:35 - 05:01
SIN
-
ORD
21h 26m
1 stop
United Airlines Logo
15:35 - 06:15
ORD
-
SIN
25h 40m
1 stop
S$ 1,418United Airlines
Booking Insights

KAYAK's insights & trends for Singapore to Chicago flights

Get data-powered insights and trends into flights from Singapore to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a return flight from Singapore to Chicago?

This analysis is based on the cheapest return trip price found on KAYAK in the last 12 months by searching for a flight from Singapore to Chicago departing in September.

Flight prices are below average for this route right now.

Flights to Chicago from Singapore usually cost between S$ 2,328 and S$ 2,662 in September.
The lowest price found in the past 5 days was S$ 987 on Air Canada (8 Sept–15 Sept).

What is the cheapest month to fly from Singapore to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Singapore to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Singapore to Chicago is February, where tickets cost S$ 0 (return) on average. On the other hand, the most expensive months are August and July, where the average cost of round-trip tickets is S$ 2,648 and S$ 1,716 respectively.

Good to know

Low season

September

Cheapest flight

S$ 625
Best time to beat the crowds (32% less expensive on average)
Most popular time to fly (66% more expensive on average)
Flight from Singapore to Chicago O'Hare Airport

When to book flights from Singapore to Chicago

Are your dates flexible? Find out the best times to travel from Singapore to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Singapore to Chicago

  • What is the cheapest flight from Singapore to Chicago?

    In the last 5 days, the lowest price for a flight from Singapore to Chicago was S$ 625 for a one-way ticket and S$ 987 for a return.

  • Which airports will I be using when flying from Singapore to Chicago?

    When flying out of Singapore you will be using Singapore Changi. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Singapore to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Singapore to Chicago?

    Star Alliance is the only airline alliance operating flights between Singapore and Chicago.

  • Which is the best airline for flights from Singapore to Chicago, EVA Air or Japan Airlines?

    The two airlines most popular with KAYAK users for flights from Singapore to Chicago are EVA Air and Japan Airlines. With an average price for the route of S$ 1,680 and an overall rating of 8.5, EVA Air is the most popular choice. Japan Airlines is also a great choice for the route, with an average price of S$ 2,620 and an overall rating of 8.3.

  • How does KAYAK find such low prices on flights from Singapore to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Singapore to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Singapore to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Singapore is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Singapore to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Singapore with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Singapore to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines flying from Singapore to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Singapore to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Singapore to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.5
EVA AirOverall score based on 1506 reviews
8.3Comfort
8.0Entertainment
8.7Crew
8.1Food
8.4Boarding
Airline reviews

First international flight where the meals were not to my taste.

8.0 ExcellentIvonny, Jul 2026
TPE - SEA
Read more EVA Air reviews

First international flight where the meals were not to my taste.

Overall, my experience with EVA Air was mixed. The highlight was that the airline clearly tried to provide a premium dining experience by offering the Michelin-starred Kanpai Classic beef yakiniku rice. However, in the limited space of an economy-class cabin, this meal felt overly oily and not very practical to eat. The sauce and grease made it easy to get one’s hands or tray table dirty, and after the meal many passengers may need to go to the lavatory simply to wash their hands. While the food itself may be high quality, the presentation and practicality did not seem well suited to an in-flight environment. Another disappointing part was the paid Wi-Fi service. I paid for the internet package, but the service did not work properly. What made the experience more frustrating was that passengers then had to spend additional time requesting a refund, and the refund process itself was slow and inconvenient. For an international airline, I think a malfunctioning paid service should be handled more efficiently. As for the seat, I feel EVA Air’s economy-class seats may be more comfortable for Asian passengers or people with smaller body frames, but they may not be as comfortable for taller or larger Western passengers on long-haul flights. The overall cabin environment also varied during the flight. Some passengers were not very mindful of noise, cleanliness, or shared cabin etiquette, which affected the comfort of the journey. I believe clearer reminders from the airline regarding cabin manners and hygiene could help improve the overall passenger experience. In short, EVA Air has some strong points, especially in trying to offer a premium Taiwanese-style service, but there are also areas that need improvement: more practical in-flight meals, a more reliable paid Wi-Fi system, faster refund handling, and better cabin management during long-haul flights.

Other than spotty internet, great servic, comfortable and smooth flight!

Crew was good. Sometimes food was eh. The spaghetti is gross for me. First time i got food, they didn’t provide utensils so i ate with my hands. I was hungry. They gave it to me 20 mins later when a crew member came by. I would fly with them again. Nobody is perfect

Organized boarding process, superb food, lovely crew, even arrived early!

Eva airlines has very goin service, despite being low cost. Meals and fin, not amazing, restrooms always clean and staff polite and helpful

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Polite hard working crew. No complaints really. Meals were not to my liking.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

I always enjoy flying with Japanese Airlines. The whole experience is always a pleasure. This flight was no exception. Thank you Kayak for making it so easy to decide.

Overall, it was ok. The attendants are nice. It was a short flight, and I did not use the restrooms. What I was frustrated was the check-in. I was to fly from ATL to Chicago (American) then change to Japan Airline to go to Japan. I checked in, but I only got a boarding pass for the flight from Atlanta to Chicago. It said I would need to check in for a flight to Japan on Japan Airline site. When I tried to check in on JAL website, it said I need to check in American... It was very confusing.

service was excellent. crew very polite, courteous, and good service especially to passengers like me who is a wheelchair passenger

The flights were on time and the cabin crew were very nice. The only downside was that the food was not good

Very comfortab flight. The flight crew and service was terrific. The food was average at best.

Excellent service, excellent food and beverage options, plenty of legroom

Check in procedure is harder than with other airlines, infotainment system is outdated

great experience - staff were kind and attentive and food was excellent. very comfortable flight that felt much shorter than 14 hours.

JAL is an exceptional airline that shows the true heart of Japanese omotenashi service. If the option is available I’ll always chose it

I would like to add American food so tired of rice after being there for 10 days didn’t want anymore to pay an airline did not have my bag marked right so it is still sitting in O’Hare. I am home.

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

Staff was generally seeming stressed out and was a bit rude and slow. Plane left late. Pilot was very well-spoken.

I was not expecting much as i was not in a premium cabin. I was pleasantly surprised that the seat in economy plus was spacious and food was ample. Party of 5 with 2 parents and 3 kids.

Meals were adequate but could be better. Lots of movies, podcasts, tv shows. We really enjoyed using our personal headsets highly recommended. 15 hrs flight great to travel at night.

Customer service - staff was effective in getting my trip rescheduled

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

Information on your arrival and departure airports