$514 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 10/27. 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

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, Nov 10 - Wed, Nov 25
Air Canada Logo
8:50 am - 2:41 pm
SIN
-
ORD
19h 51m
1 stop
Air Canada Logo
3:40 pm - 7:00 am
ORD
-
SIN
25h 20m
1 stop
$762Air Canada
Sat, Nov 7 - Sun, Nov 22
Air Canada Logo
8:50 am - 2:41 pm
SIN
-
ORD
19h 51m
1 stop
Air Canada Logo
3:40 pm - 7:00 am
ORD
-
SIN
25h 20m
1 stop
$801Air Canada
Thu, Nov 5 - Tue, Nov 17
Air Canada Logo
8:50 am - 2:41 pm
SIN
-
ORD
19h 51m
1 stop
Air Canada Logo
3:40 pm - 7:00 am
ORD
-
SIN
25h 20m
1 stop
$810Air Canada
Thu, Nov 5 - Tue, Nov 17
Air Canada Logo
8:50 am - 9:00 am
SIN
-
ORD
38h 10m
2 stops
Air Canada Logo
3:40 pm - 7:00 am
ORD
-
SIN
25h 20m
1 stop
$819Air Canada
Tue, Nov 10 - Wed, Nov 25
Air Canada Logo
8:50 am - 10:44 pm
SIN
-
ORD
27h 54m
2 stops
Air Canada Logo
3:40 pm - 7:00 am
ORD
-
SIN
25h 20m
1 stop
$821Air Canada
Mon, Sep 7 - Wed, Sep 30
ANA Logo
11:05 am - 8:40 am
SIN
-
ORD
34h 35m
1 stop
ANA Logo
5:45 pm - 6:40 am
ORD
-
SIN
23h 55m
1 stop
$823ANA
Wed, Jul 8 - Sun, Jul 12
Air Canada Logo
6:15 am - 8:05 pm
SIN
-
ORD
26h 50m
2 stops
Air Canada Logo
5:00 am - 5:15 am
ORD
-
SIN
35h 15m
2 stops
$835Air Canada
Fri, Nov 20 - Sun, Nov 22
Korean Air Logo
10:30 pm - 8:30 am
SIN
-
ORD
24h 00m
1 stop
Korean Air Logo
11:15 am - 8:25 pm
ORD
-
SIN
43h 10m
1 stop
$841Korean Air
Sun, Sep 6 - Mon, Sep 28
Delta Logo
10:00 pm - 10:36 pm
SIN
-
MDW
37h 36m
2 stops
Delta Logo
9:49 am - 5:00 am
MDW
-
SIN
30h 11m
2 stops
$957Delta
Wed, Oct 21 - Sat, Oct 31
Delta Logo
10:00 pm - 12:33 pm
SIN
-
MDW
27h 33m
2 stops
Delta Logo
6:45 pm - 12:10 am
MDW
-
SIN
40h 25m
2 stops
$959Delta
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 February, where tickets cost $739 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 $2,040 and $1,429 respectively. For one-way flights, the best month to travel is February with an average price of $739.

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 $129.

Good to know

Low seasonFebruary
Cheapest flight$514
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 78% 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 31,498 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 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 1827 reviews
8.2Comfort
8.4Boarding
7.8Entertainment
8.7Crew
7.7Food
Airline reviews

The seats were narrower compare to other airlines traveling to Asia, which makes them uncomfortable after 6 hours The plane was worn, my tray table wasn’t level, You had to pay for WiFi and no Bluetooth option to use your own headphones. The crew was excellent in servicing the food and drinks. However I felt they needed some extra hands to serve the two sections of economy at the same time. They run out of one of the food option as they got to the rear section of the plane. Having travel on other Asian airlines during this trip; American Airlines can learn a bit from them, but I wonder if their service is geared towards a clientele that has become accustomed to not expect to much from an airline.

8.0 ExcellentAnonymous, May 2026
HND - JFK
Read more Japan Airlines reviews

The seats were narrower compare to other airlines traveling to Asia, which makes them uncomfortable after 6 hours The plane was worn, my tray table wasn’t level, You had to pay for WiFi and no Bluetooth option to use your own headphones. The crew was excellent in servicing the food and drinks. However I felt they needed some extra hands to serve the two sections of economy at the same time. They run out of one of the food option as they got to the rear section of the plane. Having travel on other Asian airlines during this trip; American Airlines can learn a bit from them, but I wonder if their service is geared towards a clientele that has become accustomed to not expect to much from an airline.

It was just a short flight. The crew was nice. No major issue.

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.

The crew was great, food was good. My concern is about the plane itself. It wasn't super clean, and during the landing process (after attendants had to take their seats) the air conditioning vent above my daughter's head started leaking a lot of water. It leaked for about 30 minutes, until we landed. I let the attendant know about the leak as we were getting off the plane, and she was very kind about saying she'd look into it. Given concerns about hygiene on planes, plus the fact that my daughter had to hold the blanket over her for 30 minutes to avoid getting soaked, that was not a great situation.

Absolutely WORST experience I’ve ever hard NEVER buy your airline ticket through a third party website, especially this one. Basically stole $1300 from me and has the WORST policy taking a WEEK to change a name on the reservation? A complete joke of a company.

There was a problem with the maintenance so missed the flight from las vegas to L.A and then L.A to Narita with japan airlines. They took care of the problem by rebooked with cathay pacific airways.

I paid for premium and it’s wasn’t what I was told I would be getting. Food wasn’t good. Should be able to pick and not be served items you dislike. Very little leg room.

I am trying to select a seat during booking but it respond that set assigment will be given during check in, and the seat assignment they give is in the middle seat and 2 row from the rest rooms, i am the person who pee a lot in this case I disturb so much the person beside me ,this trip is from Haneda to Texas, the trip from Texas to Cvg is a much better because its a smaller plane few passenger

Their in0flight movie selection is limited in size and poor in quality.

Japan airlines is a great airline. One of my favorites. The only issue I had was that I only pescatarian or I can eat vegetables, pasta, etc and both choices of meals were chicken or red meat. Most of other airlines have meat or pasta. Also usually I get an alert to order a meal prior to fly and this time I did not get one. Other than that everything was wonderful.

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
Chesterton
Munster
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.