$341 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 1/21. 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, 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, Dec 24 - Mon, Jan 5
United Airlines Logo
9:05 pm - 8:15 pmORD-SIN
33h 10m1 stop
United Airlines Logo
10:10 am - 7:49 pmSIN-ORD
23h 39m2 stops
$1,241United Airlines
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Wed, Jan 21 - Tue, Jan 27
Qatar Airways Logo
11:52 am - 8:45 amORD-SIN
30h 53m2 stops
Qatar Airways Logo
3:15 am - 7:36 pmSIN-ORD
30h 21m2 stops
$1,245Qatar Airways
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Fri, Apr 24 - Thu, Apr 30
Delta Logo
9:20 am - 5:00 amMDW-SIN
30h 40m2 stops
Delta Logo
7:30 am - 9:45 pmSIN-MDW
27h 15m2 stops
$1,251Delta
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Tue, Feb 10 - Sat, Feb 14
Multiple Airlines Logo
1:10 pm - 6:40 amORD-SIN
27h 30m2 stops
Multiple Airlines Logo
7:40 am - 12:55 pmSIN-ORD
19h 15m1 stop
$1,253Multiple Airlines
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Wed, Jan 21 - Tue, Jan 27
Multiple Airlines Logo
11:10 am - 1:05 pmMDW-SIN
35h 55m3 stops
Multiple Airlines Logo
2:00 am - 9:15 pmSIN-MDW
33h 15m2 stops
$1,255Multiple Airlines
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Wed, Jan 21 - Wed, Jan 28
Delta Logo
6:14 pm - 12:10 amMDW-SIN
39h 56m2 stops
Delta Logo
10:30 pm - 12:46 pmSIN-MDW
28h 16m2 stops
$1,264Delta
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Wed, Jan 21 - Tue, Jan 27
Multiple Airlines Logo
1:00 pm - 1:05 pmORD-SIN
34h 05m3 stops
Multiple Airlines Logo
2:00 am - 1:30 pmSIN-ORD
49h 30m2 stops
$1,264Multiple Airlines
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Sat, Dec 6 - Tue, Dec 16
Multiple Airlines Logo
10:20 am - 12:50 amORD-SIN
24h 30m1 stop
Multiple Airlines Logo
12:55 am - 6:05 amSIN-ORD
43h 10m3 stops
$1,265Multiple Airlines
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Wed, Dec 24 - Mon, Jan 5
United Airlines Logo
7:10 am - 12:55 amORD-SIN
27h 45m2 stops
United Airlines Logo
10:10 am - 6:55 pmSIN-ORD
22h 45m2 stops
$1,267United Airlines
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Sun, Jan 11 - Wed, Jan 14
China Airlines Logo
6:06 pm - 1:05 pmORD-SIN
28h 59m2 stops
China Airlines Logo
2:00 am - 11:50 pmSIN-ORD
59h 50m2 stops
$1,279China Airlines
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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 $1,860 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 seasonFebruary
Cheapest flight$341
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 63% 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 1287 reviews
8.4Boarding
8.1Food
8.3Comfort
8.6Crew
8.0Entertainment
Airline reviews

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

10.0 ExcellentWalter, Nov 2025TPE - BKK
Read more EVA Air reviews

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.

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.

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.

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

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

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.

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!

Crew was great. But a bit understaffed. The business class seat, etc were dated. But comfortable. Some legs had entertainment system from a decade ago. Selections were rather poor. Food was mediocre at best. Actually poor for business class standards. I liked the lounge in Hong Kong. Showers were great. Food was nice.

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.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

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!

This is my 2nd time with the Turkish airline. Would definitely recommend. In stability we connected to Indiago would not recommend, very cramped seating. No inflight entertainment..service was inferior.

I wouldn't know what the flight was like. AI canceled my flight reservation!! There's no way to speak to an actual human to fix the issue! NEVER AGAIN! ALWAYS BOOK YOUR FLIGHT DIRECTLY WITH THE AIRLINE NEVER GO THROUGH KAYAK OR JUSTFLY.COM!!

Paying extra for premium seats was wasted. Turkish Airlines takes 2 seats for bassinet. The lady next to me had a baby with bassinet Bassinet was in front of my seat

Rude staff. I would avoid using the word racist but definitely partially or discriminatory. My 72 yrs old mother who is also disabled was traveling on this flight. She was the second passenger boarded to the plane. The First elderly couple ahead of my mother were allowed to use the airplane bathroom but my mother was denied entry stating it was for safety reasons. My mother objected the the couple in front of her were allowed but hostess still stated that due to the flight safety reasons she can’t use it. Even my mother explained that he is using blood pressure medication that’s why she have to use the restroom frequently but the crew continued arguing her. At one point the Mae attendent even suggested that if that’s the case my mother can urinate in her seat. The level of disrespect against an elderly lady is beyond my comprehension. This matter will be taken to the social media to shame the employees involved.

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.