$469 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 5/24. 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.
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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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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.

Recent round-trip flight deals from Singapore to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Singapore to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Korean Air Logo
1:30 am - 9:30 amSIN-ORD
21h 00m1 stop
Korean Air Logo
11:05 am - 5:00 amORD-SIN
27h 55m1 stop
$922Korean Air
Find Deal
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 - 8:25 pmORD-SIN
43h 20m1 stop
$930Korean Air
Find Deal
Sun, Oct 26 - Thu, Nov 13
 Logo
2:00 am - 5:04 amSIN-ORD
40h 04m2 stops
 Logo
6:50 pm - 12:40 amORD-SIN
39h 50m2 stops
Sun, Oct 26 - Thu, Nov 13
United Airlines Logo
8:45 am - 8:03 pmSIN-ORD
24h 18m1 stop
United Airlines Logo
6:25 pm - 6:15 amORD-SIN
22h 50m1 stop
$944United Airlines
Find Deal
Wed, Sep 17 - Tue, Sep 30
 Logo
2:00 am - 5:04 amSIN-ORD
40h 04m2 stops
 Logo
5:10 pm - 1:05 pmORD-SIN
29h 55m2 stops
Sun, Oct 26 - Thu, Nov 13
EVA Air Logo
3:10 pm - 5:40 amSIN-ORD
27h 30m2 stops
EVA Air Logo
5:58 pm - 12:00 pmORD-SIN
29h 02m2 stops
$1,053EVA Air
Find Deal
Tue, May 27 - Tue, Jun 3
Cathay Pacific Logo
1:50 am - 2:25 pmSIN-ORD
25h 35m1 stop
Cathay Pacific Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
$1,073Cathay Pacific
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Tue, Jun 17 - Fri, Jun 27
Cathay Pacific Logo
1:50 am - 2:25 pmSIN-ORD
25h 35m1 stop
Cathay Pacific Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
$1,075Cathay Pacific
Find Deal
Tue, Jun 17 - Fri, Jun 27
EVA Air Logo
1:10 pm - 9:00 pmSIN-ORD
20h 50m1 stop
EVA Air Logo
5:58 pm - 1:50 pmORD-SIN
30h 52m2 stops
$1,078EVA Air
Find Deal
Tue, May 27 - Tue, Jun 3
United Airlines Logo
8:40 pm - 6:24 amSIN-ORD
22h 44m1 stop
United Airlines Logo
4:25 pm - 6:15 amORD-SIN
24h 50m1 stop
$1,257United Airlines
Find Deal
Fri, Sep 19 - Wed, Oct 1
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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 February, where tickets cost $1,004 on average for return flights. On the other hand, the most expensive months are August and January, where the average cost of tickets from Singapore is $1,484 and $1,446 respectively. For one-way flights, the best month to travel is February with an average price of $1,004.

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. For the absolute cheapest price, our data suggests you should book 8 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 $137.


Good to know

Low seasonJanuary
High seasonJune
Cheapest flight$469
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly with an average 6% 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 10,485 direct flights from within Singapore to Chicago. The most common day for departures is Sunday, with 15% 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.

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.
8.4
EVA AirOverall score based on 1186 reviews
8.0Entertainment
8.3Comfort
8.4Boarding
8.6Crew
8.1Food
Airline reviews

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

8.0 ExcellentAnonymous, Mar 2025TPE - IAH
Read more EVA Air reviews

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

Everything is good staff is polite and helpful flights are on time sub sandwhich for a snack was good with a bottle of water only thing maybe more variety of food like breakfast or dinner depends on the time

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.

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

Excellent food. Good service. Crammed Premium Economy seats. I Asked to change seats during check in. They told me the flight was fully booked. But on board I saw empty seats where I could have been easily relocated.

delayed and the cabin crew was like trainees.. a bit careless and not so pleasing to their job

Except for crying babies all was ok although the movie selection wasn't the best.

The staff was marvelous. The entertainment options were terrible, old or 2nd rate movies. I was unable to entertain myself for 18 hours-it made it seem even longer. Note: I thought about upgrading but your information about what was included was unclear. Are the seats bigger? Are there current moves? What kind of food do you get? Would the upgrade compare to Delta? Just saying the upgrade is better didn’t convince me and I regret not flying Delta.

Boarding was good. It will be nice to have beer anytime. I asked for a beer at tea time & I was refused. Quite disappointed

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

very professional and very attentive to my Special Needs as I required a Wheel Chair and assistance to board

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.

Highly impressive. On time. Smooth and fast boarding and disembarkment. Really great service

It was okay overall but the food was very, very bad.

flight delayed 45 mins - missed connection - 1 hr layover became 8 hr layover waiting for next flight -

Baggage delayed for 2 days and still chasing for reimbursement of basis items. Very horrible customer care service.

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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