$558 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 4/20. 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

Sun, Mar 15 - Fri, Apr 17
United Airlines Logo
10:20 pm - 6:19 am
SIN
-
ORD
20h 59m
1 stop
United Airlines Logo
10:45 pm - 6:35 pm
ORD
-
SIN
30h 50m
1 stop
$951United Airlines
Tue, Apr 14 - Tue, Apr 21
United Airlines Logo
9:00 am - 9:38 pm
SIN
-
ORD
25h 38m
1 stop
United Airlines Logo
3:45 pm - 6:45 am
ORD
-
SIN
26h 00m
1 stop
$952United Airlines
Thu, Jun 25 - Sat, Jul 11
United Airlines Logo
8:45 am - 8:24 pm
SIN
-
ORD
24h 39m
1 stop
United Airlines Logo
9:33 pm - 6:15 am
ORD
-
SIN
43h 42m
1 stop
$953United Airlines
Fri, Mar 13 - Sun, Mar 22
United Airlines Logo
10:20 pm - 12:59 am
SIN
-
ORD
39h 39m
1 stop
United Airlines Logo
7:50 pm - 8:15 pm
ORD
-
SIN
35h 25m
1 stop
$954United Airlines
Sun, Mar 15 - Mon, Apr 13
Delta Logo
10:30 pm - 11:54 pm
SIN
-
ORD
38h 24m
2 stops
Delta Logo
7:45 pm - 7:15 pm
ORD
-
SIN
34h 30m
2 stops
$965Delta
Sun, Apr 19 - Tue, Apr 21
Multiple Airlines Logo
1:45 pm - 6:39 am
SIN
-
ORD
29h 54m
2 stops
Multiple Airlines Logo
7:24 pm - 12:35 pm
ORD
-
SIN
28h 11m
2 stops
$968Multiple Airlines
Tue, Jun 16 - Tue, Jun 30
Multiple Airlines Logo
1:45 pm - 6:20 am
SIN
-
ORD
29h 35m
2 stops
Multiple Airlines Logo
6:53 pm - 12:35 pm
ORD
-
SIN
28h 42m
2 stops
$976Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Turkish Airlines Logo
11:40 am - 6:25 pm
SIN
-
ORD
44h 45m
1 stop
Turkish Airlines Logo
9:20 pm - 10:00 am
ORD
-
SIN
23h 40m
1 stop
$1,002Turkish Airlines
Mon, Mar 16 - Thu, Apr 16
Delta Logo
10:30 pm - 10:31 pm
SIN
-
MDW
37h 01m
2 stops
Delta Logo
6:00 am - 5:00 am
MDW
-
SIN
34h 00m
2 stops
$1,076Delta
Tue, Apr 21 - Thu, Apr 30
Korean Air Logo
7:30 am - 10:28 pm
SIN
-
MDW
27h 58m
2 stops
Korean Air Logo
9:27 am - 11:55 pm
MDW
-
SIN
25h 28m
2 stops
$1,154Korean Air
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 $774 on average for one-way flights. On the other hand, the most expensive months are January and June, where the average cost of tickets from Singapore is $1,429 and $1,219 respectively. For return trips, the best month to travel is February with an average price of $774.

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, with an average flight price of $141.

Good to know

Low seasonJanuary
Cheapest flight$558
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly with an average 15% 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 13,190 direct flights from within Singapore to Chicago. The most common day for departures is Monday, 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.
7.4
United AirlinesOverall score based on 9342 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

10.0 ExcellentDr. Joseph, Feb 2026
DCA - ORD
Read more United Airlines reviews

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

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
Chesterton
Munster
Schererville
Porter
Monticello
Griffith
Saint John

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.