$336 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 8/20. 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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Best Singapore Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Singapore
Singapore1 stop$692
Singapore
Singapore1 stop$692

Cheap Flights from Chicago to Singapore

 
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

Thu, Aug 28 - Wed, Sep 3
Cathay Pacific Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
Cathay Pacific Logo
1:50 am - 2:25 pmSIN-ORD
25h 35m1 stop
$692Cathay Pacific
Find Deal
Wed, Aug 27 - Wed, Sep 3
Cathay Pacific Logo
4:00 pm - 5:30 amORD-SIN
24h 30m1 stop
Cathay Pacific Logo
8:05 pm - 2:25 pmSIN-ORD
31h 20m1 stop
$697Cathay Pacific
Find Deal
Mon, Oct 20 - Sat, Oct 25
Air India Logo
12:00 pm - 7:15 amORD-SIN
30h 15m1 stop
Air India Logo
11:00 pm - 7:30 amSIN-ORD
45h 30m1 stop
$704Air India
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Sun, Aug 10 - Wed, Sep 10
Air India Logo
12:15 pm - 9:45 pmORD-SIN
44h 30m1 stop
Air India Logo
11:00 pm - 7:25 amSIN-ORD
45h 25m1 stop
$734Air India
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Mon, Aug 18 - Mon, Aug 25
Delta Logo
9:31 am - 5:00 amMDW-SIN
30h 29m2 stops
Delta Logo
10:30 pm - 9:44 pmSIN-MDW
36h 14m2 stops
$1,139Delta
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Mon, Aug 18 - Mon, Aug 25
Delta Logo
9:15 am - 5:00 amMDW-SIN
30h 45m2 stops
Delta Logo
10:30 pm - 9:44 pmSIN-MDW
36h 14m2 stops
$1,140Delta
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Mon, Aug 18 - Sun, Aug 24
 Logo
9:31 am - 11:40 pmMDW-SIN
25h 09m2 stops
 Logo
1:10 am - 12:28 pmSIN-MDW
24h 18m2 stops
$1,188
Find Deal
Mon, Aug 18 - Sun, Aug 24
 Logo
9:31 am - 11:40 pmMDW-SIN
25h 09m2 stops
 Logo
1:10 am - 12:28 pmSIN-MDW
24h 18m2 stops
$1,189
Find Deal
Mon, Aug 18 - Fri, Aug 22
Korean Air Logo
9:31 am - 11:40 pmMDW-SIN
25h 09m2 stops
Korean Air Logo
1:10 am - 12:28 pmSIN-MDW
24h 18m2 stops
$1,636Korean Air
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Fri, Sep 19 - Fri, Sep 26
Korean Air Logo
9:35 am - 11:40 pmMDW-SIN
25h 05m2 stops
Korean Air Logo
10:30 pm - 12:28 pmSIN-MDW
26h 58m2 stops
$1,732Korean Air
Find Deal
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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 $877 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,765 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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.


Good to know

Low seasonAugust
High seasonDecember
Cheapest flight$336
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 53% 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 1214 reviews
8.1Food
8.0Entertainment
8.6Crew
8.3Comfort
8.4Boarding
Airline reviews

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

8.0 ExcellentKaye, Jul 2025JFK - TPE
Read more EVA Air reviews

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.

Clean plane, friendly crew, mostly on-time departure. Negativo since there were no snacks offered. Cold drinks only was fine due to turbulence, but nothing to eat? Really?

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.

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

If I had blood clots, that window seat would've killed me for certain.

The food and service was great. You have to pay a lot for in flight Internet though which is lame.

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!

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

flight delayed 45 mins - missed connection - 1 hr layover became 8 hr layover waiting for next flight -

Fast boarding flight on time boarded plane back to front instead of stupid zone groups like US airlines do...

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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

flight with heavy turbulence old boeing 777 rest wasnt clean dashboard doesn’t work

Light and recline did not work on my seat. Very uncomfortable and could not read in the dark

Bad experience; they are not good anymore. They charge too much for luggage seat are so uncomfortable, Flight delays which may miss your next flight, they don’t care if you miss the flight or not. Zero customer services for front desk representatives Istanbul's airport I’m not using this airline any more.

I’ve been traveling for 20 years. I tried Turkish airline for the first time horrible horrible service and it would be my last time even if I get offer for a free ticket, I will not accept it. They have races and the worst Flight attendant

It wasn't good. I didn’t understand. They changed 320 dollars for 2 luggage. My ticket was regular and I paid almost 1200.00 dollars. Why they did charge? I want my money back.. thanks Yılmaz polat

Very punctual, the onboard staff was friendly and correct, the flight was fortunately very calm, the toilets were clean, in short, an excellent experience Thanks

Ordered Vegan meal - it was ok, but not exceptional. Seat ok row 39 middle section aisle. Nearly full flight - crew was busy but they did the best they could. There was a USB A port at the seat. I listened to my own music and only looked at flight information. One nice thing was the connection information was made available in the screen.

Very nice and friendly crew. Boarding system can be improved.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

I am very tall. All airline seats are a bit uncomfortable.

Bad experience boarding and flight got delayed didn’t make it to my next flight

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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