$315 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 9/11. 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.
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1 adult, Economy

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Cheap Flights from Chicago to Singapore

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Singapore
Singapore1 stop$703
Singapore
Singapore1 stop$703

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, Feb 9 - Mon, Feb 23
Cathay Pacific Logo
2:40 pm - 1:05 pmORD-SIN
32h 25m1 stop
Cathay Pacific Logo
8:15 pm - 1:00 pmSIN-ORD
30h 45m1 stop
$703Cathay Pacific
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Thu, Nov 20 - Wed, Dec 3
Cathay Pacific Logo
2:40 pm - 11:55 amORD-SIN
31h 15m1 stop
Cathay Pacific Logo
8:15 pm - 1:00 pmSIN-ORD
30h 45m1 stop
$704Cathay Pacific
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Sun, Oct 5 - Sat, Oct 11
United Airlines Logo
9:13 pm - 6:25 pmORD-SIN
32h 12m1 stop
United Airlines Logo
8:45 am - 7:35 pmSIN-ORD
23h 50m2 stops
$705United Airlines
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Sun, Oct 5 - Tue, Oct 14
ANA Logo
5:45 pm - 6:40 amORD-SIN
23h 55m1 stop
ANA Logo
6:15 am - 2:55 pmSIN-ORD
21h 40m1 stop
$721ANA
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Sat, Oct 4 - Fri, Oct 10
United Airlines Logo
6:32 pm - 6:15 amORD-SIN
22h 43m1 stop
United Airlines Logo
8:45 am - 12:54 amSIN-ORD
29h 09m1 stop
$743United Airlines
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Thu, Nov 20 - Wed, Dec 3
 Logo
6:00 am - 12:50 amORD-SIN
28h 50m2 stops
 Logo
8:15 am - 10:30 pmSIN-ORD
28h 15m2 stops
Wed, Oct 29 - Tue, Nov 4
ANA Logo
7:10 am - 12:55 amORD-SIN
28h 45m2 stops
ANA Logo
10:45 am - 5:16 amSIN-ORD
32h 31m2 stops
$810ANA
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Wed, Oct 29 - Wed, Nov 12
Delta Logo
6:00 am - 5:00 amMDW-SIN
34h 00m2 stops
Delta Logo
10:40 am - 11:32 pmSIN-MDW
26h 52m2 stops
$904Delta
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Wed, Oct 29 - Wed, Nov 5
Delta Logo
9:35 am - 5:00 amMDW-SIN
30h 25m2 stops
Delta Logo
10:40 am - 12:28 pmSIN-MDW
39h 48m2 stops
$1,022Delta
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Wed, Sep 24 - Sat, Sep 27
 Logo
9:35 am - 11:40 pmMDW-SIN
25h 05m2 stops
 Logo
1:10 am - 12:28 pmSIN-MDW
24h 18m2 stops
$1,413
Find Deal
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 February, when tickets cost $851 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,846 and $1,428 respectively.

What’s the cheapest day of the week to fly from Chicago to Singapore?

The average price of all round-trip flights from Chicago to Singapore clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Singapore, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Thursdays.

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 10 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$315
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 61% 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.

  • What is the cheapest time of day to fly to Singapore?

    The cheapest time of day to fly to Singapore is generally in the afternoon, when round-trip flights cost $1,156 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Singapore is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,411.

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.
8.4
EVA AirOverall score based on 1235 reviews
8.3Comfort
8.1Food
8.4Boarding
8.0Entertainment
8.6Crew
Airline reviews

Very good service and food. Crew was professional and considerate. Cabin and restrooms were kept clean

10.0 ExcellentDale, Aug 2025SFO - TPE
Read more EVA Air reviews

Very good service and food. Crew was professional and considerate. Cabin and restrooms were kept clean

Flight Attendants could have been nicer and food portions could be bigger.

Great experience, comfort and food is delicious. Always great service and one time

The food from Los Angeles to Taipei made me throw up. The flight is also not comfort. But the staffs are very friendly and nice.

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

For the price, it was better than other airlines; quality of food and service was very good.

I appreciate the email reminders for online check-in which made my entry to the lines less stressful. The flight was on schedule and on time. The baording staff were proactively helpful and approachable. The airplane inflight food, entertainment and comfies as well as provisions are excellent even in the economy seating. The airline transfer was smooth and easy! Luggage safe and intact! Thank you EVA airline for making my trip a reliable safe and comfortable experience.

I was sleep when they brought the food. They had put a note on my seat. There was no food when I asked for food later. There was just one main meal served in this 14 hours flight. They offered me sandwich with ham which I don’t eat since I am pescatarian. Long story short I had to wait to get to TPE to get something to eat. I am extremely disappointed from the service. I have been flying EVA since I was 1 year old. Perhaps no more EVA for me. Seems EVA glorious day is long gone

The food is quite mediocre. I had spaghetti and the tomato based sauce was quite salty and there were no other flavors, no spices used in the sauce.

The app was awful. No accurate info. Paying for internet is a negative (Delta is free). The crew was very nice for the most part although you are not guaranteed to get good service. Some crew would ignore requests for things as simple as a cup of water if you were sleeping when the first serving was made. Food was great. Male crew member was exceptionally kind and responsive.

they are deley vancouver to hankong 3 hour after honkong 20 hour stay there honkong not visa approved and they cant help to visa so we are stay in airport 20 hour even honkong staf very bad person they cant do for us 6 hour we arround they said you there you go there waste time next time i dont want to go cathay stay in honkong

I was only given 2 meals, and my screen showed that there were 3 meals. Second meal was 1-2 hours late according to the screen.

Just want to do a little more clean up so does not smell like urine.

Entertainment for kids was good. Good was terrible, needs lots of work.

I've stomach problems after 2 hours of flight, Iris, the flight purser not only did her best to make me feel comfortable, she went above and beyond providing pain relievers medicines and ointment. She look and found a doctor passenger on the flight to provide advise. She even report on ground staffs about my condition and provide wheelchair upon arrival. Kudos to her and Cathay Pacific!

I have a Peanut Allergy and the Steward staff were very accommodating in ensuring my safety as my allergy is life threatening. Very professional and so vested in their profession.

Everything was fine and I have no complaints or things to note.

Overall, it was ok. However, the food was very sub-par.

The economy seats are much indeed roomier. Meals needs improvement.

When comes to Taiwan airlines China airlines is the best rest are pure trash

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

my experience was great with Turkish airlines . the problem i encountered was with kayak booking. When I booked . it showed that im allowed a bag . and when I got to the airport, i had to pay $165 for one bag.

Not up to Business Class standards. Two of the three toilets were out of order. The hostesses were aware and didn’t show any responsible act to do something. Food quality was not what we expect from Turkish hospitality. Overall we were not impressed and disappointed.

During mid flight, try to get a flight attendant to help I couldn’t find one Otherwise, everything was perfect

I was not given basinett seat.The connecting flight was missed due to airline fault i was not accomodated for hotel.Drinks were normt served frewuently.Never travelling again on tirkish airlines.I always travel wiyh family by turkish airline but no more.zero stars

The crew were very hospitable and pleasant. The food was pretty good. Unfortunately, there was a flight delay of more than 2 hours. We're not sure why but it appeared to be outside the control of Turkish Airlines.

Bough tickets with luggage, but made me pay at Airport as well

The economy seat was so uncomfortable, had not enough leg room for 13 hours flight, front seat basket was broken and couldn’t hold anything, food quality was horrible( we got food poisoned ) we charged for logged which used to be free. We paid too much for this flight and very disappointed. Turkish air line better to make satisfy and respect people instead of find different way to scam people.

This is really the rating of two flights. JFK to IST then IST to NQZ. New York to Istanbul was good. Good crew and all positives. The flight to Astana was so bad that brought it all down. Crew was nonexistent above the minimum, seats were cramped, and it was hot on the plane. Turkish Airlines seems to be slipping down to US based carriers level.

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

Everything was very good, except that the plane was an hour and a half late

My flight from New York to Canada and Canada to Brisbane was canceled, so I had to take united airlines instead flight from New York to Dubai then layover in Dubai 8 hours then from Dubai to Brisbane it was extremely difficult for me , it was a nightmare flying with Canadian airlines unfortunately.

I found the boarding easy and my seat was very comfortable as I had a lot of leg room. I am not too happy that I no longer have lounge access even though I used to get it with my TD credit card.

Flight cancelled. Major disruption to our travel. Do not use Air Canada from KC. To few flights.

Real smooth and easy, Real good leg room in coach!

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Re luggage I carried a backpack only. I did not check any bags in. However there were other passengers with carry on luggage going in the plane. My question is why are others allowed to have a carry on luggage inside the plane? Shouldn’t they have dropped it off at the gate? I’m asking because I could have brought the same thing instead of a backpack only. Please clarify for future reference. Thank you.

Like the service. Very hard to communicate or contact when have problems

Very bad, flight was cancelled due to strike and staff was unable to rebook us

They rescheduled me and I had no issues with the new flight

Air Canada is my new fave airline..I plan to use when I can. No complaints at all just rave compliments for the staff and airline.

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.

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