$445 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 4/27. 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

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Flight Deals

Book Cheap Chicago to Singapore Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Singapore 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 Chicago to Singapore

Mon, Jun 1 - Mon, Jun 8
Air India Logo
1:10 pm - 12:10 pm
ORD
-
SIN
34h 00m
1 stop
Air India Logo
11:00 pm - 11:10 am
SIN
-
ORD
49h 10m
2 stops
$891Air India
Mon, Aug 24 - Mon, Sep 14
Air India Logo
1:10 pm - 12:10 pm
ORD
-
SIN
34h 00m
1 stop
Air India Logo
11:00 pm - 11:10 am
SIN
-
ORD
49h 10m
2 stops
$901Air India
Mon, Jun 1 - Wed, Jun 10
Air India Logo
1:10 pm - 12:10 pm
ORD
-
SIN
34h 00m
1 stop
Air India Logo
11:00 pm - 11:10 am
SIN
-
ORD
49h 10m
2 stops
$920Air India
Mon, Aug 24 - Tue, Sep 15
Air India Logo
1:10 pm - 7:25 am
ORD
-
SIN
29h 15m
1 stop
Air India Logo
1:10 pm - 11:10 am
SIN
-
ORD
35h 00m
2 stops
$925Air India
Mon, Jun 1 - Thu, Sep 24
Air India Logo
1:10 pm - 7:25 am
ORD
-
SIN
29h 15m
1 stop
Air India Logo
1:10 pm - 11:10 am
SIN
-
ORD
35h 00m
2 stops
$927Air India
Mon, Aug 24 - Sun, Sep 13
Air India Logo
1:10 pm - 7:25 am
ORD
-
SIN
29h 15m
1 stop
Air India Logo
8:25 am - 11:10 am
SIN
-
ORD
39h 45m
2 stops
$931Air India
Mon, Jun 1 - Mon, Jun 8
Air India Logo
1:10 pm - 9:45 pm
ORD
-
SIN
43h 35m
1 stop
Air India Logo
11:00 pm - 11:10 am
SIN
-
ORD
49h 10m
2 stops
$932Air India
Mon, Aug 24 - Mon, Sep 14
Air India Logo
1:10 pm - 12:10 pm
ORD
-
SIN
34h 00m
1 stop
Air India Logo
11:00 pm - 11:10 am
SIN
-
ORD
49h 10m
2 stops
$938Air India
Mon, May 4 - Wed, May 13
Delta Logo
9:29 am - 5:00 am
MDW
-
SIN
30h 31m
2 stops
Delta Logo
7:30 am - 9:09 pm
SIN
-
MDW
26h 39m
2 stops
$1,154Delta
Sun, May 3 - Tue, May 12
Delta Logo
6:00 am - 5:00 am
MDW
-
SIN
34h 00m
2 stops
Delta Logo
10:00 pm - 9:09 pm
SIN
-
MDW
36h 09m
2 stops
$1,204Delta
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, 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 from Chicago to Singapore is September, when tickets cost $851 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $1,944 and $1,442 respectively.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, 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 on the flight from Chicago to Singapore, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low seasonApril
Cheapest flight$417
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 70% increase in price.
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    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 from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    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 from Chicago to Singapore 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 from Chicago to Singapore?

    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 from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? 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.
8.5
EVA AirOverall score based on 1422 reviews
8.3Comfort
8.6Crew
8.4Boarding
8.0Entertainment
8.1Food
Airline reviews

Never went. Got rescheduled with Phillipine Airlines to Bali, which was fine.

2.0 MediocreWilliam, Apr 2026
SEA - TPE
Read more EVA Air reviews

Never went. Got rescheduled with Phillipine Airlines to Bali, which was fine.

I am really satisfied with Eva Air and will definitely fly with them again.

The flight from SEA to Taipei was on a Boeing 787-10. Economy seats were unacceptably cramped and the seats themselves were old and lacking cushion. I'm only 5'3" and couldn't cross my legs as my knees were up against the seat in front of me! I could not get WiFi to work most of the time on both flights and crew were invisible except to serve meals. The onboard entertainment also did not work reliably and was very hard to hear through the provided earbuds. The Asian vegetarian meals were interesting. I hope they can provide a fully vegan option though these meals seemed to be already. I appreciate their providing these meals options for vegans. I don't think I'll fly a 787-10 if I can help it. It was the definition of a sardine can in Economy.

My luggage was lost and didnt arrive in manila yesterday. And until now im still waiting for the confirmation if my luggage is teady for pick up in terminal 1

I always preferred EVA air every time I visit Philippines. It’s just this time that I have to be very early to make sure that I don’t miss my flight due to TSA problem. There’s only one choice of food serve which you use to have 2 on our flight from Taiwan to Philippines . Otherwise I will still use EVA air in my future flight.

Service was great. Flight schedule was on time. Staffs are friendly.

Overall was good but it would be good if the airline is providing snack such as sandwich or instant noodle between meals for LA to Taipei

Amazing customer service. BUT!! It would be nice if the flight attendants SMILE a little more, I know they are doing their job, but it is importantly to smile back and be warm to passengers. Nobody is trying to hit on them, it’s just being polite. So, please Taiwanese flight attendants: SMILE MORE WHEN YOU INTERACT WITH PAYING CUSTOMERS

It was easy going check in was easy and pretty fast entertainment was up to date on movies and food was ok

Premium Economy seats were more comfortable than other airlines I have recently been on. Great staff. Food was unremarkable.

My seat had many issues. First the chair was broken where reclining was difficult. My usb plug was also broken so charging was impossible.

The flight from Hong Kong to Hyderabad didn’t have any power points to charge my mobile. Given we are no longer allowed to use power banks, giving customers the ability to charge even on short flights is critical part of the overall experience.

when i ask for help all the crew members had a look like why are you calling me? very terse and rude.

Good service and food. However, we paid over $400 for aisle seats for my disabled husband and me, and we were given window and middle seats. This was dangerous for our health condition on such a long flight. We needed to stand up and walk around frequently, but we were stuck in our seats. Please give us a refund of our seat payment since you chose not to honor our request.

Very bad Instead 22 hour it take me more that 35 hour to arrive from Los Angeles to Phuket and they changed my flight in Hong Kong to Shanghai china and in order to get my bag I was forced to vet china visa entrry

There could have been more options on the entertainment section Nothing was available for non English speaking passengers

I didn't have much experience with Cathay Pacific airlines because of delay and missed connections, the bulk of the trip was on Japan Airlines.

Flight delayed first from bad weather, then after boarding there was a problem with the plane. We had to get off and onto another plane...connections were missed and the trip took an additional 10 hours!! Pre-paid seatting was not honored due ro last minute carrier changes. Most of the trip was on Japan Airline.

The crew, pilots and flight attendants were all amazing. What could be better is reinforcing that seats cannot be reclined at departure and landing. I had a person seated in front of me who had her seat all the way inclined, including during take-off - after the crew asked her to seat upright. Cathay Pacific should reinforce this safety request and perhaps penalize those who don't follow it. I felt very unsafe with this person limiting my space and perhaps putting my life in danger in the "unlikely" case of an emergency.

Crew and food were great in-flight. We had a 2 hour delay, no communication, and just got left in a limbo. The crew arrived late and they were running checkouts on the plane (which is important, but why not doing it earlier?) Cathay did nothing to about the delay, and a lot of people missed their connection flights. I had to run and got stuck at checkpoint, which made my entire trip very unpleasant. Got to my gate 5 mins prior to them closing it.

The seats seems abit small and the reclining is too much, the seat in front of me came back too much and made it uncomfortable for me.

As a first time flyer with Turkish Airlines. My experience was very good due to the factor that there were to many passengers on the my first flight compared to my connecting flight. However, I know that nothing is perfect and all companies are trying to accommodate their passengers to the best way possible. I will always say, a FEW INCHES will go LONG WAY. That's something all airliners should consider, and not only the money aspect!!! A long time commitment is better than one time service! Thank you

Flight was delayed. While standing at the gate, a note appeared on the sign saying the gate had changed to a gate far away. No member of the Turkish airlines team got on the microphone to instruct passengers to go to the other gate, to ignore the chiron, etc. Finally, the message disappeared. Eventually, the flight began to board. Very slowly. More slowly than I experience with other airlines. Though Istanbul may just be slow . . . In all other ways, great flight, great entertainment (top notch movies), great service, excellent food, comfortable lie-flat seat, dimmed lights, etc.

Staff at the airport wasn't helpful or friendly. Probably the worst airport experience I have ever had, going and coming. The staff on the plane was better. Still not super friendly or personable. However, they were not rude like airport staff. They ran out of certain menu items. Maybe could have been prepared better? Overall just ok.

It was a pleasant experience. In flight entertainment could have been better

The desk crew at the LAX crew could do better. A girl named Mahesi was very abrasive and unfriendly. She needs a better customer service uproar.

It was peaceful excited We enjoyed it always Turkish peaceful excited

Istanbul to Lahore flight was less than standard for international business class cabins. Seat did not were not flat and it did not operate easily. I had to push buttons hard repeatedly to operate the seat. I was in 5A seat

IAH to Istanbul was outstanding across the board. The flight from Istanbul to Male was good, not great.

the cabin was kept too hot. couldn't sleep as a result

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

1 hour delay meant missed my connecting flight and 1st day of holiday

The seats seemed smaller than other business class offerings. The entertainment menu was limited. Flight crew was good.

Dear Team, I purchased a full travel package that included 2 checked bags through you and JustFly. However, when I arrived at the airport, my ticket showed 0 checked bags. Since I was traveling internationally to India with 2 bags, It was a $200 per bag at the counter, which was extremely disappointing. For an international trip, why would I ever choose a no‑bag option for only $20–$30 less? This seems like an error in the booking process, and I am requesting clarification and a resolution. I have called JustFly and on phone for 1 hr :53 min and they couldn't help till I show some kind of proof etc which isn't possible but besides that love your service and using it for years !

Good one but just notice that you have to ask several time to get water or coffee .

The flight was over 1 hour late taking off ,when I arrived in Abu Dhabi ,I missed my connecting flight to Bangkok so I had to wait almost 6 hours for my flight arriving in Bangkok at 6:30 am ,So I missed a whole day of my vacation and my hotel room sat empty so I paid for hotel days that I was not there. In Abu Dhabi there was a woman that worked the desk at transfers that was so professional, courteous , helpful,and may I say absolutely beautiful .she got me food vouchers for my layover and was a very calming presence. Besides that I will never use Etihad again I will pay the Xtra money . I'm sure they won't read or see this but it's my "2 cents" I'll use an airline that respects me and my hard earned dollars

On this flight...fine. The one from India to Abu Dahbi, awful.

I booked and paid for a Business Class seat for myself and my wife. 4 hours before the flight i get a call saying the plane they sent doesn't have the correct layout to accommodate all the business class seats they sold me 3 months earlier at a premium of $1500 a ticket. So they have to bump me from Business to Economy and will give me a $400 credit (total of $800 for both seats) that I could turn in at Abu Dahbi for $400 in US cash. They then promised a row that we could have to ourselves and the arm rests would go up so we could spread out for each of us. My wife was taken care of but I was put in the exit row with the flight attendents set as part of the three...and the arm rest did not go up. When we got to Abu Dahbi, they would not exchange our credit for cash as promised. Very disappointed they took my money 3 months ago and refused to reimburse for the change in seats or follow the promises made.

It was fantastic. The flight from Chicago to Abu Dahbi was fantastic. The crew, food and service were amazing. Everything was handled by the crew member assigned to us , Nicholas, was usually done before we asked for it. Highly recommend Etihad!

I missed my flight ,staff unhelpful, they sat and watched me wait ,gangway door closed, English was a problem no announcement I was on time now I missed my month vacation ,lost 1400 bucks no refund I'm sick to my stomach

It’s a business class ticket but they didn’t give a lounge access

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.