$512 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 to Chicago departing on 10/30. 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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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

Thu, Sep 24 - Sun, Sep 27
Air Canada Logo
7:00 am - 2:43 pm
SIN
-
ORD
20h 43m
1 stop
Air Canada Logo
3:40 pm - 5:15 am
ORD
-
SIN
24h 35m
1 stop
$774Air Canada
Sat, Dec 26 - Sun, Jan 10
Air Canada Logo
8:40 am - 2:37 pm
SIN
-
ORD
19h 57m
1 stop
Air Canada Logo
3:35 pm - 7:00 am
ORD
-
SIN
25h 25m
1 stop
$775Air Canada
Thu, Sep 24 - Sun, Sep 27
Air Canada Logo
7:00 am - 2:43 pm
SIN
-
ORD
20h 43m
1 stop
Air Canada Logo
2:15 pm - 5:15 am
ORD
-
SIN
26h 00m
2 stops
$776Air Canada
Sat, Dec 26 - Sun, Jan 10
Air Canada Logo
8:40 am - 7:58 pm
SIN
-
ORD
25h 18m
2 stops
Air Canada Logo
10:05 am - 7:00 am
ORD
-
SIN
30h 55m
2 stops
$786Air Canada
Sat, Dec 26 - Sun, Jan 10
Air Canada Logo
8:40 am - 2:37 pm
SIN
-
ORD
19h 57m
1 stop
Air Canada Logo
12:50 pm - 7:00 am
ORD
-
SIN
28h 10m
2 stops
$789Air Canada
Tue, Sep 22 - Sun, Sep 27
Multiple Airlines Logo
1:45 am - 2:43 pm
SIN
-
ORD
25h 58m
2 stops
Multiple Airlines Logo
3:40 pm - 5:15 am
ORD
-
SIN
24h 35m
1 stop
$803Multiple Airlines
Thu, Sep 24 - Sun, Sep 27
Air Canada Logo
7:00 am - 4:35 pm
SIN
-
ORD
22h 35m
2 stops
Air Canada Logo
10:00 am - 5:15 am
ORD
-
SIN
30h 15m
2 stops
$809Air Canada
Thu, Oct 15 - Mon, Oct 19
Air Canada Logo
7:00 am - 8:06 pm
SIN
-
ORD
26h 06m
1 stop
Air Canada Logo
7:45 pm - 5:15 am
ORD
-
SIN
44h 30m
1 stop
$810Air Canada
Wed, Sep 23 - Mon, Sep 28
Delta Logo
10:00 pm - 10:45 pm
SIN
-
MDW
37h 45m
2 stops
Delta Logo
5:11 pm - 7:15 pm
MDW
-
SIN
37h 04m
2 stops
$1,150Delta
Wed, Aug 26 - Sun, Aug 30
Delta Logo
1:25 am - 4:15 pm
SIN
-
MDW
27h 50m
2 stops
Delta Logo
9:59 am - 11:55 pm
MDW
-
SIN
24h 56m
2 stops
$1,259Delta
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.

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 $141.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$512
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 68% 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.

  • 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.

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

    Each week there are around 30,546 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.

Reviews of the top airline 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.
8.3
Japan AirlinesOverall score based on 1872 reviews
8.2Comfort
8.7Crew
7.8Entertainment
7.7Food
8.4Boarding
Airline reviews

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.

8.0 ExcellentMami, May 2026
ATL - ORD
Read more Japan Airlines reviews

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.

Food was excellent, the crew was exceptionally friendly, and the seats were comfortable. Bathroom were also kept very clean and odor free.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

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.
First Class flights to Chicago
Business Class flights to Chicago
Premium Economy Class flights to Chicago
Economy Class flights to Chicago