$355 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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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

Wed, Mar 11 - Mon, Mar 16
Air India Logo
2:30 pm - 9:45 pm
ORD
-
SIN
42h 15m
1 stop
Air India Logo
11:00 pm - 12:30 pm
SIN
-
ORD
50h 30m
2 stops
$648Air India
Wed, Feb 11 - Sun, Feb 15
Air India Logo
1:30 pm - 7:00 am
ORD
-
SIN
27h 30m
1 stop
Air India Logo
8:00 pm - 11:30 am
SIN
-
ORD
29h 30m
2 stops
$651Air India
Mon, Mar 2 - Wed, Mar 18
Air India Logo
1:30 pm - 9:45 pm
ORD
-
SIN
42h 15m
1 stop
Air India Logo
11:00 pm - 12:30 pm
SIN
-
ORD
50h 30m
2 stops
$677Air India
Mon, Feb 9 - Sun, Mar 8
Air India Logo
1:30 pm - 9:45 pm
ORD
-
SIN
42h 15m
1 stop
Air India Logo
8:00 pm - 12:30 pm
SIN
-
ORD
29h 30m
2 stops
$680Air India
Mon, Mar 9 - Mon, Mar 16
Air India Logo
2:30 pm - 7:00 am
ORD
-
SIN
27h 30m
1 stop
Air India Logo
11:00 pm - 12:30 pm
SIN
-
ORD
50h 30m
2 stops
$692Air India
Mon, Mar 9 - Mon, Mar 16
Air India Logo
2:30 pm - 7:00 am
ORD
-
SIN
27h 30m
1 stop
Air India Logo
11:00 pm - 12:30 pm
SIN
-
ORD
50h 30m
2 stops
$696Air India
Mon, Mar 2 - Mon, Mar 16
Air India Logo
1:30 pm - 7:00 am
ORD
-
SIN
27h 30m
1 stop
Air India Logo
11:00 pm - 12:30 pm
SIN
-
ORD
50h 30m
2 stops
$701Air India
Mon, Mar 9 - Tue, Mar 24
Air India Logo
2:30 pm - 9:45 pm
ORD
-
SIN
42h 15m
1 stop
Air India Logo
8:20 am - 12:30 pm
SIN
-
ORD
41h 10m
2 stops
$707Air India
Mon, Mar 2 - Mon, Mar 9
Delta Logo
6:40 pm - 12:10 am
MDW
-
SIN
39h 30m
2 stops
Delta Logo
10:30 pm - 10:31 pm
SIN
-
MDW
37h 01m
2 stops
$894Delta
Mon, Feb 9 - Sun, Mar 8
Delta Logo
6:35 pm - 12:10 am
MDW
-
SIN
39h 35m
2 stops
Delta Logo
10:30 pm - 10:31 pm
SIN
-
MDW
37h 01m
2 stops
$900Delta
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 $807 (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 $1,424 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 2 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$355
Best time to beat the crowds with an average 29% 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.
8.4
EVA AirOverall score based on 1325 reviews
8.3Comfort
8.4Boarding
8.1Food
8.0Entertainment
8.6Crew
Airline reviews

Very nice, I feel I got good value for the price.

10.0 ExcellentJimmy, Jan 2026
ORD - TPE
Read more EVA Air reviews

Very nice, I feel I got good value for the price.

Amazing one of the best airlines i have ever traveled with. I live with medical issues called psoriatic arthritis and was in pain on the flight. The flight crew made sure I had fresh ice pack ever hour. Going above an beyond with service and care ⭐️⭐️⭐️⭐️⭐️.

Certain flight crew member were rude and short with me when I asked questions.

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.

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.

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.

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

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

They oversold the tickets by one which was my ticket so I didn’t have a ticket till last second

Not good. I was supposed to be in Mint but got in economy class

Service was slow and checked bag was off last evening when flying business

Turkish Airline canceled our tickets in the very last minute, with our luggage and everything else, all prepared and good to go. It’s clear that they sold the tickets for better money to someone else. Bad, Bad, Bad business!!!

Awful seating. Bad food. Staff only have one bottle of water and no cans.

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.

I waiting for 2 hrs to retrieve my luggage. Didn't get home till 3am.

The flight left late and I didn’t get a glass of bubbly upon boarding (which I’m used to when booking business class on other flights), but otherwise it was a pleasant flight with lovely, helpful crew members and I enjoyed my meal.

Good flight. It's great you can easily go anx help yourself to snacks and water. Crew friendly and helpful. Everything ran very smoothly.

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Couldn't fit knees, only 1 toilet working, didn't get anything to drink cause the stewards were not able to get to us

Flight was canceled for a reason they knew hours before but did not mention. Next the gate chnage from 37 to 38 at least 10 times. Ridiculous.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

Our biggest complaint about Air Canada is that if you don’t like your seat during check-in, there’s a fee to move elsewhere. On our flight from YUL to FFL, we were charged to change seats—just regular seats. What’s maddening is that the plane wasn’t even full; there were even a few people sleeping in the middle row sections (entire rows, completely empty), using them as beds. In my opinion, charging passengers for seat changes is a cash grab by Air Canada. They are definitely not the airline they were back in the day. I suppose they need to gouge the consumer now that they pay their attendants while on ground. One out of 10.

Nothing specific. Cabin temperature was too high for some reason.

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.