$346 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 2/4. 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

Tue, Jan 20 - Thu, Jan 22
Multiple Airlines Logo
10:35 am - 1:05 pm
MDW
-
SIN
36h 30m2 stops
Multiple Airlines Logo
2:00 am - 10:50 pm
SIN
-
MDW
34h 50m2 stops
$1,281Multiple Airlines
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
2:10 pm - 1:05 pm
MDW
-
SIN
32h 55m2 stops
Multiple Airlines Logo
2:25 pm - 2:55 pm
SIN
-
MDW
38h 30m3 stops
$1,295Multiple Airlines
Fri, Jan 23 - Sat, Jan 31
Multiple Airlines Logo
11:10 am - 1:05 pm
MDW
-
SIN
35h 55m3 stops
Multiple Airlines Logo
2:25 pm - 12:30 pm
SIN
-
MDW
36h 05m2 stops
$1,296Multiple Airlines
Thu, Mar 19 - Sat, Mar 28
Delta Logo
6:30 am - 5:00 am
MDW
-
SIN
33h 30m2 stops
Delta Logo
10:30 pm - 4:53 pm
SIN
-
MDW
31h 23m2 stops
$1,301Delta
Wed, Mar 4 - Sat, Mar 28
Delta Logo
6:45 am - 5:00 am
ORD
-
SIN
32h 15m2 stops
Delta Logo
1:35 am - 9:00 pm
SIN
-
ORD
32h 25m2 stops
$1,301Delta
Tue, Dec 23 - Sat, Dec 27
United Airlines Logo
10:00 pm - 8:15 pm
ORD
-
SIN
32h 15m2 stops
United Airlines Logo
10:10 am - 5:04 pm
SIN
-
ORD
20h 54m1 stop
$1,355United Airlines
Tue, Jan 6 - Sun, Jan 18
EVA Air Logo
1:09 pm - 12:05 pm
ORD
-
SIN
32h 56m2 stops
EVA Air Logo
3:45 pm - 7:35 pm
SIN
-
ORD
41h 50m1 stop
$1,370EVA Air
Tue, Jan 6 - Sun, Jan 18
EVA Air Logo
1:09 pm - 2:30 pm
ORD
-
SIN
35h 21m2 stops
EVA Air Logo
1:15 pm - 11:50 pm
SIN
-
ORD
48h 35m2 stops
$1,392EVA Air
Tue, Jan 6 - Sun, Jan 18
Qatar Airways Logo
6:50 pm - 9:15 pm
ORD
-
SIN
36h 25m1 stop
Qatar Airways Logo
8:15 pm - 2:30 pm
SIN
-
ORD
32h 15m1 stop
$1,470Qatar Airways
Tue, Dec 23 - Fri, Dec 26
United Airlines Logo
10:10 pm - 8:15 pm
ORD
-
SIN
32h 05m1 stop
United Airlines Logo
10:20 pm - 11:25 am
SIN
-
ORD
27h 05m1 stop
$1,501United 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 February, when tickets cost $801 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,913 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 16 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$346
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 68% 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.
8.5
EVA AirOverall score based on 1297 reviews
8.6Crew
8.1Food
8.4Boarding
8.3Comfort
8.0Entertainment
Airline reviews

We were very impressed with the modern plane its amenities, as well as the services of flight attendants.

10.0 ExcellentVip, Dec 2025
LAX - TPE
Read more EVA Air reviews

We were very impressed with the modern plane its amenities, as well as the services of flight attendants.

Everything was great, however the seats in the back are very small. Not as Comfortable as I would have liked.

Eva airlines has very goin service, despite being low cost. Meals and fin, not amazing, restrooms always clean and staff polite and helpful

My ticket was with EVA Airlines, but Asiana Airlines was the ground crew for EVA Airlines. Me and my family member finally received our boarding passes after waiting to check-in, which took over 30 minutes. I had never done a tax refund before, so I crossed immigration without going to customs to receive a stamp for my tax refund. When I went to the tax kiosk on the other side of the immigration gate, NICE Tax Refund asked me to talk to an airline staff member. I could not find any airline staff member, so I went to the Information Desk. The woman at the Information Desk told me and showed me a sign that read that I needed an airline staff member to accompany me to cross immigration again. The woman at the Information Desk phoned EVA Airlines and Asiana Airlines. I also phoned, but there was no answer. There was still 80 minutes before my flight would leave. I waited for 45 minutes. I spoke to Information, not one time, but two times and the woman assured me that this situation happens often and it is nothing to worry about as the airport is small and once the airline staff arrives, it would only take 10 minutes to go get the stamp and I would be able to make my flight. Then, 35 minutes before my flight was scheduled to leave an Asiana Airline employee, accompanied by the woman from the Information Desk came. Asiana asked me to confirm whether I wanted the customs declaration stamp. I answered yes. Then, she said she would like to state that I should take full responsibility if I could not make my flight. She asked whether I wanted her to proceed to contact a staff member to take me to get the stamp. This was very suspicious as there was still 35 minutes remaining until the flight took off. I directly said to her that the question was very strange, but as there was enough time remaining, I did not see a problem and wanted a staff member to accompany me to get the stamp. She went away and came back 5 minutes later and asked me whether I had the item I wanted to declare on me and how many people were traveling with me. I told her I had the item with me and I was here with a family member. She then went away again for another 5 minutes. When she came back she asked whether all members would not be traveling as well. I stated that I am not sure why me or my family member should not board the airplane. At this point, it became apparent that she was not helpful, so I tried to talk to other airline staff. I also talked to a woman wearing a reflective safety vest, who was organizing the gate bollards for boarding and she said she would take me after boarding. When I asked, how I would board the plane, she then said, you will not be able to. I then talked to a man, who spoke Mandarin and appeared to work for EVA Airlines. He told me it was my fault and not his and tried to re-direct me to another person. He was not busy at all. At this point, it became apparent that, Asiana Airlines and EVA Airlines, were more interested in delaying and preventing me from boarding the airplane. In the time the airline staff wasted arguing with me, they could have just brought me to receive the stamp. It seemed apparent that I was not going to receive the stamp or the tax refund, so I stepped into the boarding queue line. Again, the airline staff, the woman in the reflective safety vest asked me to confirm that I would not be getting on the airplane. I was already boarding! There was written signage of the procedure at your airport’s Information Desk. Then, I was passed to multiple airline staff that were not willing to assist accordingly. There was no one at the customs declaration counter and no one else from the airport to assist me. EVA and Asiana Airlines both avoided responsibility and delayed the procedure. They were rude and indirect about the situation with every attempt to prevent me from boarding. Deterring foreigners to depart from a foreign country over tax refund issues is unlawful.

The crew very accommodating and food too is good. Keep up the good work

The crews are very efficient. Other airlines should learn from them when it comes to boarding and departing from the airplane. They also display efficiency in serving meals. They don't keep the aisles blocked for hours like some other airlines. The food is poor. Generally the food was unrecognizable and poorly prepared. The only thing that made it better than US flag carriers is that there was a fresh fruit bowl with each meal.

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.

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.

It was good. The planes needed to be updated though, they were dated and the entertainment systems were old. Service was amazing. The pre-booked meals were lacklustre.

Super delayed. Unnecessary. Need more competent people doing logistics to keep things moving on time. Totally unacceptable.

Flew from lax economy on cathay 777. Seat configuration 3-4-3. When the forward seat reclines it feels like someone is leaning forward and staring you. If you are slightly big tray tables will touch your abdomen even with seats upright. AVOID this above 777 configuration at all cost for a long flight. However their Airbus 350 3-3-3 configuration felt spacious and Seats wider.

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?

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

Seats in the absolute back row of the plane even though we booked ages ago :( Crew was awesome though

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

it was like a banya -so hot... They did provide a great experience with special food. one toilet broke midflight In general it was a peaceful and relaxing flight - for business class it was good.

Chicago to Istanbul was a much better experience than I expected since I’m more accustomed to Qatar Airways business class. The business lounge in the Istanbul airport was amazing - loved the lockers and phone charging stations, and the bathroom was a spa experience in itself. The onward leg from Istanbul to Karachi was utterly disappointing. Terrible plane, and I felt like I was in economy - the seats don’t come near to lying flat and the food was mediocre. What a sad downgrade - it isn’t as though the ticket on that leg was cheaper. So, on that front, there’s no contest with Qatar airways.

Second leg of Turkish Airline with Indigo is disaster for following reason. 1) You have to carry your cabin bags through ladder to boeing 777 because it was parked somewhere in parking lot and was not given a gate to board passengers and this seems to be people traveling to and fro from those flights and is not issue with flight itself. 2) I choose non vegetarian food on Turkish portal way ahead of checkin to entire trip, However the Indigo flight gave me random veg food saying they code veg food code from Turkish. 3) Indigo did not served any alcoholic beverages stating some weird reason which is non nonsensical. 4)Indigo have TV screens in front of you but it displays nothing except "Welcome Onboard" with annoying white black ground in dark flight. This is the most stupidest and annoying part because you are held hostage for 7 hours and only thing you could do is stare back at white screen which does not have entertainment package or even flight tracker. Such a shame.

nice and clean plane but the seats and the comfort was not what i expected. i expected more based on all the ads and reviews that i've read. I guess you get what you pay for in economy.

Overall it was good. Food was bad. I ordered gluten free vegetarian meal. But I got gluten free chicken for my long flight from Seattle to Istanbul. I don’t eat any kind of meat. Second meal I got eggplant with meat which I couldn’t eat. I don’t understand why we can’t get gluten free vegetarian meal for a 12 hour flight. I eat the bread and that was it.

Worse worse worse, i would not recommend this airline to anyone. Istanbul airport maybe State of the Art facility but staff is rude, only works if they get tips, and they push you to give tips even though my family had spent $50 in tips. Airline staff doesn't speak english so you really can't understand them. It was a nightmare travelling with Turkish. Never again.

As a big guy the seats are way too small for me. Would prefer more comfortable seats on these long haul flights.

My flight was canceled 1 minute before boarding. The customer service was owful, no one could tell us what was going happened. I spent 30hrs instead of 15 from Washington DC to Brussels. No apologie or help

Boeing 777 is a bad choice for a such a long flight.

The staff at IST airport could have been more helpful. Too much wasted time and the plane from IST to KHI was just horrible. The plane was not clean and smelled bad!

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

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.