$505 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 to Chicago departing on 9/14. 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 for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Singapore to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 round-trip flight deals from Singapore to Chicago

Tue, Sep 2 - Tue, Sep 9
ANA Logo
10:10 pm - 3:10 pmSIN-ORD
30h 00m1 stop
ANA Logo
12:40 pm - 5:15 pmORD-SIN
39h 35m1 stop
$819ANA
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Fri, Oct 31 - Sat, Nov 8
Air Canada Logo
8:50 am - 5:10 pmSIN-ORD
45h 20m2 stops
Air Canada Logo
3:35 pm - 7:00 amORD-SIN
49h 25m2 stops
$820Air Canada
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Sat, Nov 22 - Mon, Dec 1
Korean Air Logo
1:30 am - 8:30 amSIN-ORD
21h 00m1 stop
Korean Air Logo
11:05 am - 8:25 pmORD-SIN
43h 20m1 stop
$931Korean Air
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Sun, Oct 26 - Thu, Nov 13
Korean Air Logo
1:30 am - 9:30 amSIN-ORD
21h 00m1 stop
Korean Air Logo
11:05 am - 12:10 amORD-SIN
23h 05m1 stop
$934Korean Air
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Tue, Sep 9 - Thu, Sep 25
 Logo
2:35 pm - 6:14 pmSIN-ORD
40h 39m2 stops
 Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
Wed, Sep 10 - Tue, Sep 23
 Logo
12:20 am - 10:43 pmSIN-ORD
35h 23m2 stops
 Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
Sat, Sep 20 - Sat, Sep 27
United Airlines Logo
8:40 pm - 5:23 amSIN-ORD
21h 43m1 stop
United Airlines Logo
9:13 pm - 6:25 pmORD-SIN
32h 12m1 stop
$955United Airlines
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Tue, Sep 2 - Mon, Sep 22
United Airlines Logo
8:45 am - 5:08 pmSIN-ORD
21h 23m1 stop
United Airlines Logo
3:47 pm - 6:15 amORD-SIN
25h 28m1 stop
$956United Airlines
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Thu, Sep 18 - Thu, Sep 25
Delta Logo
7:30 am - 8:49 amSIN-MDW
38h 19m2 stops
Delta Logo
9:35 am - 11:40 pmMDW-SIN
25h 05m2 stops
$972Delta
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Sun, Sep 21 - Sun, Sep 28
Delta Logo
7:30 am - 8:53 amSIN-MDW
38h 23m2 stops
Delta Logo
9:35 am - 5:00 amMDW-SIN
30h 25m2 stops
$1,328Delta
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Booking Insights

KAYAK's insights & trends for flights to Chicago

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

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights 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 to Chicago is October, where tickets cost $906 on average for return flights. On the other hand, the most expensive months are January and August, where the average cost of tickets from Singapore is $1,446 and $1,328 respectively. For one-way flights, the best month to travel is October with an average price of $906.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights 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, you should book around 4 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $151.

Good to know

Low seasonJanuary
Cheapest flight$505
Best time to beat the crowds but there is an average 29% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Singapore to Chicago

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles if you land in Chicago Greater Rockford.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Monday where round-trip tickets can be as cheap as $1,116. On the other hand, the most expensive day to fly is Thursday, where round-trip prices are $1,495 on average.

  • How does KAYAK find such low prices on flights 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 to Chicago.

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

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when round-trip flights cost $1,166 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,286.

  • How many direct flights to Chicago are there each week?

    Each week there are around 12,761 direct flights from within Singapore to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying from Singapore to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Singapore to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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.
7.6
Cathay PacificOverall score based on 955 reviews
7.9Boarding
7.8Entertainment
7.3Food
7.6Comfort
8.1Crew
Airline reviews

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.

8.0 ExcellentAnonymous, Jul 2025HKG - LAX
Read more Cathay Pacific reviews

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.

The only problem I had was not being able to download my boarding passes prior to arriving at the airport. Everything else was perfect.

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.

Crew was great. But a bit understaffed. The business class seat, etc were dated. But comfortable. Some legs had entertainment system from a decade ago. Selections were rather poor. Food was mediocre at best. Actually poor for business class standards. I liked the lounge in Hong Kong. Showers were great. Food was nice.

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

Everything was fine and I have no complaints or things to note.

The flight was delayed for 30 mins. The overall experience was good.

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.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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