$342 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 3/1. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Singapore

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Wed, Mar 25 - Wed, Apr 1
United Airlines Logo
6:20 pm - 7:00 am
ORD
-
SIN
23h 40m
1 stop
United Airlines Logo
8:35 pm - 6:20 am
SIN
-
ORD
22h 45m
1 stop
$783United Airlines
Wed, Mar 18 - Wed, Apr 8
United Airlines Logo
6:17 am - 8:15 pm
ORD
-
SIN
24h 58m
1 stop
United Airlines Logo
9:00 am - 8:27 pm
SIN
-
ORD
24h 27m
1 stop
$790United Airlines
Wed, Mar 18 - Wed, Apr 8
United Airlines Logo
11:15 am - 7:00 am
ORD
-
SIN
30h 45m
2 stops
United Airlines Logo
8:35 pm - 5:27 am
SIN
-
ORD
21h 52m
1 stop
$795United Airlines
Sun, Mar 22 - Mon, Apr 6
Air India Logo
2:30 pm - 9:45 pm
ORD
-
SIN
42h 15m
1 stop
Air India Logo
11:00 pm - 11:10 am
SIN
-
ORD
49h 10m
2 stops
$838Air India
Mon, Apr 6 - Fri, Apr 17
Etihad Airways Logo
2:00 pm - 9:40 am
ORD
-
SIN
30h 40m
1 stop
Etihad Airways Logo
9:00 pm - 8:35 am
SIN
-
ORD
24h 35m
1 stop
$860Etihad Airways
Fri, Feb 27 - Fri, Mar 6
Etihad Airways Logo
1:10 pm - 9:35 am
ORD
-
SIN
30h 25m
1 stop
Etihad Airways Logo
7:25 pm - 7:35 am
SIN
-
ORD
26h 10m
1 stop
$867Etihad Airways
Tue, May 12 - Tue, May 26
Multiple Airlines Logo
3:55 pm - 12:35 pm
MDW
-
SIN
31h 40m
2 stops
Multiple Airlines Logo
1:45 pm - 5:45 am
SIN
-
MDW
29h 00m
2 stops
$1,229Multiple Airlines
Thu, Apr 30 - Thu, May 14
Multiple Airlines Logo
6:10 pm - 12:35 pm
MDW
-
SIN
29h 25m
2 stops
Multiple Airlines Logo
1:45 pm - 11:10 am
SIN
-
MDW
34h 25m
2 stops
$1,278Multiple Airlines
Mon, Mar 16 - Thu, Mar 26
Delta Logo
9:35 am - 12:10 am
MDW
-
SIN
25h 35m
2 stops
Delta Logo
10:40 am - 10:31 pm
SIN
-
MDW
24h 51m
2 stops
$1,286Delta
Mon, Mar 16 - Thu, Mar 26
Delta Logo
9:35 am - 5:00 am
MDW
-
SIN
30h 25m
2 stops
Delta Logo
10:40 am - 8:50 am
SIN
-
MDW
35h 10m
2 stops
$1,291Delta
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 $849 (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 $1,418 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 seasonFebruary
Cheapest flight$342
Best time to beat the crowds with an average 23% 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.

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 1353 reviews
8.4Boarding
8.3Comfort
8.6Crew
8.1Food
8.0Entertainment
Airline reviews

It was easy going check in was easy and pretty fast entertainment was up to date on movies and food was ok

8.0 ExcellentAnonymous, Feb 2026
IAH - TPE
Read more EVA Air reviews

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.

From checking at the airport to end of flights, attentive and caring personnel, comfortable seating, great food. I plan on using EVA again. Thank you, all.

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.

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

There could have been more options on the entertainment section Nothing was available for non English speaking passengers

I was mid plane and they were already out of the main beef entree....ugh!

We flew economy light. We did not want to check bags and we had free 1 bag, but just had back packs with small personal item. Try as we may could only get bags down to 17lbs each. So we put 2 lbs from one bag into other and checked it. I think if someone has a checked bag allowance and chose not to use it , it would benefit both parties to bump carry on weight up to the next level of 22lbs or 10kgs. Just a thought.

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.

Flight from Hong Kong to LAX was late, the plane was grubby, overcrowded and hot. I recently flew Starlux and that was a MUCH better experience.

Extensive delays, poor organization to board people, as it felt like chaos to get inside of the plane. No lines, everyone gathering together like a mayhem, very confusing. Passengers out of hand and rude, which is not the airlines fault. However, there should be rules, e.g., not letting one passenger take 2+ spots in the overhead bin.

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

The flight was just ok, but the vendor made it exceptio ally bard to manage my own reservation and would not give me access. The blocked all of the one time pins to come to their email address which caused me.to go through them eceryrime to get seats see rhe reservation and even get wheelchair access for my sick 71 year old uncle. They only xommunicates via a bot which gave me incorrect info. I thought this was Kayak and not underprivileged. They ruined his trip, did not get him aisle seats and made it impossible to purchase extra leg room. It was a horrible experience. He was taken to hospital on arrival only to find he had blood clots and pnemonia while trying to navigate the airport. This vendor is very irresponsible and the airline could not access his info.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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.

After arriving in Istanbul, the transit information on the electronic board showed a tight departure time, and the gate changed in the middle, making it difficult to make it on time.

Typically good service onboard but baggage delay in airport was significant

My, Syed Zawar Hussein Shirazi frequently flyer membership number was not included on my boarding pass from O’Hare to Istanbul despite my reminder to the attendant at check in. Further she forgot to give me my boarding pass form Istanbul to Lahore and she needs to improve her customer service, please 🙏

Everything about that day was great I was happy with how things went as a first time traveling with the airline thank you for all that you’ve doing by taking us there to our various destinations thanks.

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.

Was delayed at every point/ connection. Luggages missing for 5days. Had no medications for diabetes and high B/p. when bags where finally delivered on the 30th, the insulin and ozempic were no longer patent, as the ice pack had since dissolved and the authenticity of the med is now questionable, since they must be refrigerated. Please have them refund my bag fees. I should sue them for all the inconveniences caused to me.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

Overall very good 👍 the only disappointment was that I pre ordered a vegan meal and the longest flight YVR-SIN wasn’t on board even though check in said it was and my email booking shows that confirmed ✅ luckily some passengers were not on board and there was a vegetarian meal available, but still, I think you should know because every all the other flights were vegan meals except for the longest so that was a bit of a concern at the beginning of the flight.

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.

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.