$562 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 3/11. 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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Everything you should know

Cheapest round-trip
$901
Typical prices: $958-$975
Korean Air
Wed 2/4Wed 2/18
SIN - ORD • 1 stop
Cheapest one-way
$535
Typical prices: $612-$949
Multiple Airlines
Wed 3/11
SIN - ORD • 3 stops
When to travel
October
Cheapest • 19% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Wed, Feb 4 - Wed, Feb 18
Korean Air Logo
1:35 am - 8:40 amSIN-ORD
21h 05m1 stop
Korean Air Logo
11:25 am - 8:25 pmORD-SIN
43h 00m1 stop
$901Korean Air
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Thu, Feb 5 - Wed, Feb 18
Air Canada Logo
8:50 am - 2:41 pmSIN-ORD
19h 51m1 stop
Air Canada Logo
3:35 pm - 7:00 amORD-SIN
25h 25m1 stop
$902Air Canada
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Thu, Feb 5 - Wed, Feb 18
Air Canada Logo
8:50 am - 9:13 amSIN-ORD
38h 23m2 stops
Air Canada Logo
3:35 pm - 7:00 amORD-SIN
25h 25m1 stop
$903Air Canada
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Tue, Feb 10 - Fri, Feb 20
United Airlines Logo
10:10 am - 5:44 amSIN-ORD
33h 34m1 stop
United Airlines Logo
4:20 pm - 8:00 amORD-SIN
25h 40m1 stop
$922United Airlines
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Mon, Dec 22 - Wed, Jan 7
United Airlines Logo
10:20 pm - 5:58 amSIN-ORD
21h 38m1 stop
United Airlines Logo
6:47 am - 8:15 pmORD-SIN
23h 28m1 stop
$923United Airlines
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Wed, Jan 28 - Sun, Feb 1
United Airlines Logo
10:20 pm - 5:44 amSIN-ORD
21h 24m1 stop
United Airlines Logo
5:16 pm - 8:00 amORD-SIN
24h 44m1 stop
$924United Airlines
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Thu, Jan 15 - Fri, Jan 23
United Airlines Logo
10:20 pm - 2:53 pmSIN-ORD
30h 33m1 stop
United Airlines Logo
4:16 pm - 8:00 amORD-SIN
25h 44m1 stop
$926United Airlines
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Thu, Feb 5 - Wed, Feb 18
Air Canada Logo
8:50 am - 7:45 pmSIN-ORD
24h 55m2 stops
Air Canada Logo
7:15 am - 12:55 amORD-SIN
27h 40m2 stops
$927Air Canada
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Wed, Feb 4 - Wed, Feb 18
Delta Logo
1:35 am - 10:22 pmSIN-MDW
34h 47m2 stops
Delta Logo
12:46 pm - 8:25 pmMDW-SIN
41h 39m2 stops
$948Delta
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Wed, Feb 4 - Wed, Feb 18
Delta Logo
1:35 am - 9:00 pmSIN-ORD
33h 25m2 stops
Delta Logo
2:46 pm - 8:25 pmORD-SIN
39h 39m2 stops
$948Delta
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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 one-way flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from Singapore is $1,561 and $1,284 respectively. For return trips, the best month to travel is October with an average price of $906.

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 $148.

Good to know

Low seasonJanuary
Cheapest flight$535
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Singapore to Chicago O'Hare Airport

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 tickets can be as cheap as $1,116. On the other hand, the most expensive day to fly is Thursday, where 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 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 15,115 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 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 1068 reviews
8.1Crew
7.9Boarding
7.8Entertainment
7.3Food
7.6Comfort
Airline reviews

Not much of anything could have been done better unless I had a first class ticket. I was literally 15 hours with an airline in the economy class. Very professional friendly and attentive crew. Good airline food, clean cabin, seating area and bathrooms. I've been 4 times back-and-forth with Cathay Pacific, and I would not choose another airline for this trip. Five out of five stars.

10.0 ExcellentErnest, Nov 2025HKG - SFO
Read more Cathay Pacific reviews

Not much of anything could have been done better unless I had a first class ticket. I was literally 15 hours with an airline in the economy class. Very professional friendly and attentive crew. Good airline food, clean cabin, seating area and bathrooms. I've been 4 times back-and-forth with Cathay Pacific, and I would not choose another airline for this trip. Five out of five stars.

Well- trained, cheerful onboard staff. Business class seating and storage were excellent. Outstanding range of food choices, though quality ranged from just OK (seasonal rice and beef dish) to outstanding ( congee and soup noodles with beef brisket). But what can you expect; it's on a plane. I couldn't figure out the remote control, but touch screen worked well. My wife and I (in our 60s), didnt find much to watch from the Entertainment choices. We mostly watched the flight maps. The bedding did the job but is unwieldy and ends up in a clump, with one-third falling on the floor.

First time tying out business class with this airline, hat a disappointment, never returning. We didn’t get the meal as requested from Singapore to HKG flight. While meals served connecting flight, crew takes meal order based off passenger membership status by giving the. Priority selection of meals. It was a battle, plain disappointment, not worth the hype, price, class as categorized/ advertised

Leg room wasn't that great. Other than that it was a good flight

Issues: 1) the charging issue as described in my previous survey 2) when I requested diet coke during the breakfast time, it is not available. Why? I can't drink diet coke in the morning? 3) when I tried to transfer to this flight, its gate information was not available to me?

The lead business class attendant was excellent. Made a point of greeting you and knowing your name by the time you leave.

A lot of things Never flying with this airline again Had an emergency landing

Chicken pieces were too big with pasta. Need to be smaller.

Overall pretty good experience. It would be nice to have caught the attendants even they were flying down the aisle with snacks, and if they could cater to multiple dietary restrictions (bland and no lactose. The customer service chat is a bad experience), but otherwise no complaints.

Boarding at the airport was not well managed. Otherwise, had a good flight sitting in the first row (which I paid for). Crew was pretty friendly, and flight was smooth.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

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
Schererville
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.