$327 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 9/1. 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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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, Apr 27 - Thu, May 28
Air India Logo
1:15 pm - 9:45 pm
ORD
-
SIN
43h 30m
1 stop
Air India Logo
1:10 pm - 11:10 am
SIN
-
ORD
35h 00m
2 stops
$939Air India
Fri, May 15 - Mon, May 25
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
$965Air India
Wed, Sep 2 - Tue, Sep 15
Cathay Pacific Logo
4:00 pm - 11:45 am
ORD
-
SIN
30h 45m
1 stop
Cathay Pacific Logo
1:45 am - 1:55 pm
SIN
-
ORD
25h 10m
1 stop
$978Cathay Pacific
Fri, Sep 25 - Thu, Oct 1
Air Canada Logo
8:40 pm - 5:15 am
ORD
-
SIN
67h 35m
2 stops
Air Canada Logo
7:00 am - 9:21 am
SIN
-
ORD
39h 21m
2 stops
$985Air Canada
Fri, Sep 11 - Wed, Sep 16
Air Canada Logo
3:40 pm - 5:15 am
ORD
-
SIN
24h 35m
1 stop
Air Canada Logo
6:15 am - 8:12 pm
SIN
-
ORD
26h 57m
2 stops
$992Air Canada
Wed, Aug 19 - Mon, Sep 7
Cathay Pacific Logo
4:00 pm - 11:45 am
ORD
-
SIN
30h 45m
1 stop
Cathay Pacific Logo
1:25 pm - 2:20 pm
SIN
-
ORD
37h 55m
1 stop
$1,006Cathay Pacific
Tue, Aug 25 - Sun, Sep 6
Delta Logo
9:30 am - 11:55 pm
MDW
-
SIN
25h 25m
2 stops
Delta Logo
7:30 am - 9:46 pm
SIN
-
MDW
27h 16m
2 stops
$1,279Delta
Tue, May 5 - Tue, May 12
Delta Logo
6:00 am - 5:00 am
MDW
-
SIN
34h 00m
2 stops
Delta Logo
10:00 pm - 11:56 am
SIN
-
MDW
26h 56m
2 stops
$1,304Delta
Tue, Sep 22 - Tue, Oct 6
Multiple Airlines Logo
8:30 pm - 12:35 pm
MDW
-
SIN
27h 05m
2 stops
Multiple Airlines Logo
1:45 pm - 12:30 pm
SIN
-
MDW
35h 45m
2 stops
$1,377Multiple Airlines
Fri, Sep 11 - Wed, Sep 16
Multiple Airlines Logo
2:00 pm - 12:35 pm
MDW
-
SIN
33h 35m
2 stops
Multiple Airlines Logo
1:45 pm - 5:50 am
SIN
-
MDW
29h 05m
2 stops
$1,436Multiple Airlines
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 seasonMay
Cheapest flight$327
Best time to beat the crowds but there is an average 4% increase 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 1417 reviews
8.3Comfort
8.4Boarding
8.1Food
8.0Entertainment
8.7Crew
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2026
DFW - TPE
Read more EVA Air reviews

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

Service was great didn't leave on time was not good

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.

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.

My flight was suppose to be at 7:45pm to fly but it didnt fly out until 8:55 to dallas so then all of my other flights was late and delay ihad to wait at the airport for extra 14 hours to be able to get on a different plane

There were delays at boarding and landing. These events resulted in a tight transfer time in HK. Poor signage for transfers. Finally, lost luggage at final destination.

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!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

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

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

It was a problem because there was a delay where we sat before taking off from newark,then when landed in Toronto we sat on tarmac and they wouldn't let us out for a long period of time. When we finally were released to the airport in Toronto the attendant scanned our boarding pass that we were here for our connection to Brazil. We ran all the way to the gate and they said at the gate the door is shut so we can not let you on the plane. We explained that we were checked in by the attendant when we arrived at Toronto airport to go to Brazil and they should not have shut the door. We were ignored at the gate

Flight home was delayed multiple times, did not get home until 2am

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

My original flight was cancelled and then rebooked four hours later on a recovery flight, but I was checked in as stanby and had no seats so as a family of four we were concerned about not being seated altogether. Our flight then got delayed by another 1.5 hours and when seats were assigned at the gate, three of the four of us were together and we could get my wife closer, they offered no assistance.

I bought a ticket from Kayak. When I got to the airport, the was no ticket. I had to pay 5X to get to my destination. No response received from Kayak. I will NEVER use them again.

My wallet was stolen while I was sleeping on the plane.

Good boarding but extremely cold temperature in both flights (60 F!).

The whole plane smelled and felt old. The seats were very uncomfortable. Multiple delays. Extra fees.

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.