SIN - CHI

S$ 607 Find Cheap Flights from Singapore to Chicago

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 9-10. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Singapore to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Singapore to Chicago.
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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

Sat, 11 Oct - Sat, 18 Oct
Air Canada Logo
09:10 - 12:32SIN-ORD
40h 22m2 stops
Air Canada Logo
21:12 - 07:05ORD-SIN
44h 53m2 stops
S$ 1,030Air Canada
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Sun, 5 Oct - Sun, 19 Oct
Air Canada Logo
09:10 - 08:01SIN-ORD
35h 51m2 stops
Air Canada Logo
08:47 - 07:05ORD-SIN
33h 18m2 stops
S$ 1,051Air Canada
Find Deal
Mon, 13 Oct - Mon, 20 Oct
ANA Logo
06:15 - 08:40SIN-ORD
39h 25m1 stop
ANA Logo
12:40 - 06:40ORD-SIN
29h 00m1 stop
S$ 1,086ANA
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Tue, 28 Oct - Tue, 4 Nov
ANA Logo
10:45 - 05:16SIN-ORD
31h 31m2 stops
ANA Logo
16:25 - 06:55ORD-SIN
24h 30m1 stop
S$ 1,094ANA
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Sun, 19 Oct - Sun, 26 Oct
Korean Air Logo
22:30 - 09:30SIN-ORD
24h 00m1 stop
Korean Air Logo
12:15 - 05:00ORD-SIN
27h 45m1 stop
S$ 1,200Korean Air
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Sun, 19 Oct - Tue, 28 Oct
Korean Air Logo
22:30 - 09:30SIN-ORD
24h 00m1 stop
Korean Air Logo
12:15 - 00:10ORD-SIN
22h 55m1 stop
S$ 1,201Korean Air
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Sun, 5 Oct - Sun, 19 Oct
United Airlines Logo
08:45 - 00:54SIN-ORD
29h 09m1 stop
United Airlines Logo
09:00 - 06:15ORD-SIN
32h 15m1 stop
S$ 1,212United Airlines
Find Deal
Sun, 26 Oct - Thu, 13 Nov
Cathay Pacific Logo
01:25 - 14:00SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
14:40 - 05:40ORD-SIN
25h 00m1 stop
S$ 1,221Cathay Pacific
Find Deal
Sun, 26 Oct - Thu, 13 Nov
Cathay Pacific Logo
01:25 - 14:00SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
14:40 - 20:10ORD-SIN
39h 30m1 stop
S$ 1,223Cathay Pacific
Find Deal
Sat, 11 Oct - Sat, 18 Oct
United Airlines Logo
08:45 - 17:08SIN-ORD
21h 23m1 stop
United Airlines Logo
18:32 - 18:25ORD-SIN
34h 53m1 stop
S$ 1,232United Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from S$ 1,030 (return)
EVA Air
Best reviews • 8.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
October
Cheapest • 17% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
S$ 1,030
Overall average: S$ 1,371
Air Canada
Sat 11-10Sat 18-10
SIN - ORD • 2 stops
Cheapest one-way flight
S$ 607
Typical prices: S$ 854-971
Multi-carrier
Thu 9-10
SIN - ORD • 2 stops
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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?

What’s the cheapest day of the week to fly from Singapore to Chicago?

The average price of all round-trip flights from Singapore to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Singapore to Chicago, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Saturday is the most expensive.

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 October, where tickets cost S$ 1,161 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is S$ 1,804 and S$ 1,593 respectively.

How far in advance should I book a flight from Singapore to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Singapore to Chicago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flightS$ 607
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly (13% 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 3 days, the lowest price for a flight from Singapore to Chicago was S$ 474 for a one-way ticket and S$ 804 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, oneworld, and SkyTeam are the airline alliances operating flights between Singapore and Chicago, with Star Alliance being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Singapore to Chicago are EVA Air and ANA. With an average price for the route of S$ 1,525 and an overall rating of 8.4, EVA Air is the most popular choice. ANA is also a great choice for the route, with an average price of S$ 1,760 and an overall rating of 8.4.

  • 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 5 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.
8.4
EVA AirOverall score based on 1236 reviews
8.1Food
8.4Boarding
8.3Comfort
8.0Entertainment
8.6Crew
Airline reviews

Awful had to ask for a supervisor to sit with my flight companion even t booked the tickets together weeks before

4.0 OkayAnonymous, Aug 2025TPE - SEA
Read more EVA Air reviews

Awful had to ask for a supervisor to sit with my flight companion even t booked the tickets together weeks before

Very good service and food. Crew was professional and helpful. Cabin and restrooms were kept clean

EVA airlines was excellent: on time or early, safe, courteous crew. Highly recommended.

EVA! What is going on with your food!?!? Pre pandemic I used to go to Taiwan at least twice a year and always flew EVA — the food was consistently tasty for airplane food. Post pandemic, it’s not great at all. Step it up!

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. Oh and the seats were more comfortable, had more ability to lean and the headrest was much better for flight sleeping. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

Sub sandwhich for a snack through mid flight and giving a bottle water was a good idea

seats are pitched well. you don't feel too tight.

For the price, it was better than other airlines; quality of food and service was very good.

Check in process in Manila was so slow. From the time we got in line to reaching the counter we could have arrived at Taipei even if the flight was delayed for half hour.

Great but I am not sure why I was placed in zone 4 for boarding despite being an Infinity Member??? Can you explain online. Thanks

Everything was excellent. Only the fish entree in the Japanese meal was overcooked and quite dry but everything else was great

One of the best business class seats I’ve had. The lie flat seats made it comfortable to endure a 12 hour flight. Service was excellent and food was great.

Business class on ANA was awesome. There lie flat seats made it easier to sleep on a 12 hour flight. Food was great and service was excellent.

Almost 6 hours of delay with over 12 gate changes. Flight was supposed to depart around 6 and instead depart after 12am. No accommodations were offered than some snacks closer to midnight when the crew was planning to throw away some snacks.

Purchased WiFi was slow to non functional. Staff was not personable or friendly. Seats were cramped. Boarding took long but I expected that.

The crew was excellent. The flight was delayed for 20 to 25 minutes. We did arrive a bit later than expected. The AC could have been better.

Very disappointed with the seat selection. During the booking, I selected seats such that my wife and I would sit next to each other. However, during check-in, we found out that the airline changed our seats and we were seated apart; and I was stuck in the middle seat with two strangers. Very disappointing experience. We would not fly ANA next time.

Luckily I just tried to sleep. But the entertainment system was awkward to operate. I hate all this stuff with apps and adding it to your phone and all. It is a nuisance. I would prefer a good magazine or newspaper in the pocket in front of me or available.

Upgrade the comfort, food and attendants. Also we arrived in Houston in the morning. The meal they served two hours before our arrival was a dinner entree. It would have been a lot nicer and much more appropriate to have had breakfast.

During booking, I selected the seats so that my wife and I would sit next to each other. However, the airline changed our seats at boarding so that we were seated apart. Very disappointing.

I am Vegetarian also has Gluten free food. However they gave me chicken and fish which is gluten free, but i am a vegetrain and i requested crew Hindu meal vegetarian, they said they will come back. .but they never showed up even i asked 2nd time. They could have compensate. I also request airline industry to have another option Gluten Free for Vegetarin people as well. Because Vegetarin people will have gluen issue...

Just want to do a little more clean up so does not smell like urine.

Check in process at the kiosk, crew in flight and overall comfort was good. Food selection could have been better. Flight from Hong Kong to Los Angeles did not have any vegetarian main course option, it was either sea food or chicken. Being a vegetarian I could only eat yogurt and fruit. Most international flights have one vegetarian main course dish which I found missing in Cathay Pacific menu.

If I had blood clots, that window seat would've killed me for certain.

They ran out of food and were offering random food to passengers.

The food and service was great. You have to pay a lot for in flight Internet though which is lame.

Flight was delayed at the last minute for six hours. Instead of delaying it to a normal hour, they moved it to 10 pm to essentially make it a redeye. There was no compensation or benefit offered for this inconvenience. Once on the plane, Inpaid for WiFi twice with both times it not working because of a “weak WiFi signal”, according to the flight attendants. They also chose the farther possible gates in both airports from the entrance/exit, even though they were one of the few active flights left so late in the evening. Overall it was pretty horrible.

Special request meals are really below average. Vegetarian options are very limited if you didn't prebook.

Worst experience I have ever had with any airline in over 25 years.

Very noisy and careless crew on this overnight flight. They should understand customers want to sleep

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

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

Information on your arrival and departure airports

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