SIN - CHI

S$ 613 Find Cheap Flights from Singapore to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Singapore to Chicago departing on 27-11. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Singapore to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Singapore to Chicago, as well as popular online travel agencies
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 19% or moreCompare multiple travel sites with one search.

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

Free to useThere are no hidden charges or fees.

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

Flights Deals
Booking Insights
Flights Deals

Cheap Flights from Singapore to Chicago (SIN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Singapore to Chicago 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 return flight deals from Singapore to Chicago

Thu, 25 Sep - Sun, 28 Sep
Air Canada Logo
09:10 - 09:31SIN-ORD
37h 21m2 stops
Air Canada Logo
15:40 - 07:05ORD-SIN
26h 25m1 stop
S$ 867Air Canada
Find Deal
Thu, 25 Sep - Sun, 28 Sep
Air Canada Logo
09:10 - 16:51SIN-ORD
44h 41m2 stops
Air Canada Logo
19:54 - 04:00ORD-SIN
43h 06m2 stops
S$ 868Air Canada
Find Deal
Thu, 25 Sep - Wed, 26 Nov
Air Canada Logo
09:10 - 16:42SIN-ORD
20h 32m1 stop
Air Canada Logo
14:30 - 07:00ORD-SIN
26h 30m2 stops
S$ 903Air Canada
Find Deal
Mon, 25 Aug - Mon, 1 Sep
ANA Logo
22:10 - 15:20SIN-ORD
30h 10m1 stop
ANA Logo
17:45 - 06:40ORD-SIN
23h 55m1 stop
S$ 1,048ANA
Find Deal
Wed, 3 Sep - Wed, 24 Sep
ANA Logo
22:10 - 15:10SIN-ORD
30h 00m1 stop
ANA Logo
11:50 - 00:45ORD-SIN
23h 55m1 stop
S$ 1,049ANA
Find Deal
Thu, 4 Sep - Thu, 11 Sep
 Logo
11:05 - 00:29SIN-ORD
26h 24m2 stops
 Logo
07:19 - 00:45ORD-SIN
28h 26m2 stops
S$ 1,101
Find Deal
Thu, 25 Sep - Wed, 26 Nov
Delta Logo
07:30 - 08:53SIN-MDW
38h 23m2 stops
Delta Logo
06:00 - 00:10MDW-SIN
28h 10m2 stops
S$ 1,251Delta
Find Deal
Wed, 3 Sep - Thu, 25 Sep
Delta Logo
01:10 - 18:37SIN-MDW
30h 27m2 stops
Delta Logo
09:20 - 23:40MDW-SIN
25h 20m2 stops
S$ 1,255Delta
Find Deal
Mon, 11 Aug - Sun, 31 Aug
 Logo
01:10 - 12:28SIN-MDW
24h 18m2 stops
 Logo
09:31 - 23:40MDW-SIN
25h 09m2 stops
S$ 2,549
Find Deal
Tue, 12 Aug - Sun, 31 Aug
Korean Air Logo
22:30 - 12:28SIN-MDW
26h 58m2 stops
Korean Air Logo
09:31 - 23:40MDW-SIN
25h 09m2 stops
S$ 3,420Korean Air
Find Deal
Booking Insights

KAYAK's insights & trends for Singapore to Chicago flights

Get data-powered insights and trends into flights from Singapore to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Singapore to Chicago?

The average price of all round-trip flights from Singapore to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Singapore to Chicago, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Saturday is the most expensive.

What is the cheapest month to fly from Singapore to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Singapore to Chicago, 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 Singapore to Chicago is October, where tickets cost S$ 1,166 (return) on average. On the other hand, the most expensive months are January and August, where the average cost of round-trip tickets is S$ 1,862 and S$ 1,714 respectively.

How far in advance should I book a flight from Singapore to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Singapore to Chicago, 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 Singapore to Chicago, you should book around 4 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flightS$ 613
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly (8% more expensive on average)
Flight from Singapore to Chicago O'Hare Airport

When to book flights from Singapore to Chicago

Are your dates flexible? Find out the best times to travel from Singapore to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Singapore to Chicago

  • What is the cheapest flight from Singapore to Chicago?

    In the last 3 days, the lowest price for a flight from Singapore to Chicago was S$ 476 for a one-way ticket and S$ 673 for a return.

  • Which airports will I be using when flying from Singapore to Chicago?

    When flying out of Singapore you will be using Singapore Changi. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Singapore to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Singapore to Chicago?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Singapore and Chicago, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Singapore to Chicago, EVA Air or Cathay Pacific?

    The two airlines most popular with KAYAK users for flights from Singapore to Chicago are EVA Air and Cathay Pacific. With an average price for the route of S$ 1,531 and an overall rating of 8.4, EVA Air is the most popular choice. Cathay Pacific is also a great choice for the route, with an average price of S$ 1,347 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Singapore to Chicago?

    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 Singapore to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Singapore to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from 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 Singapore to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Singapore with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Singapore to Chicago?

    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 to Chicago from Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines flying from Singapore to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Singapore to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Singapore to Chicago? 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 1222 reviews
8.1Food
8.4Boarding
8.6Crew
8.0Entertainment
8.3Comfort
Airline reviews

EVA airlines was excellent: on time or early, safe, courteous crew. Highly recommended.

10.0 ExcellentAnonymous, Jul 2025TPE - JFK
Read more EVA Air reviews

EVA airlines was excellent: on time or early, safe, courteous crew. Highly recommended.

EVA! What is going on with your food!?!? Pre pandemic I used to go to Taiwan at least twice a year and always flew EVA — the food was consistently tasty for airplane food. Post pandemic, it’s not great at all. Step it up!

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

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. Oh and the seats were more comfortable, had more ability to lean and the headrest was much better for flight sleeping. 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.

Aircraft was late getting to the gate - probably due to weather. We left the gate one hour late and had to wait another hour since we lost our slot in the takeoff queue. Our box was very wet and was falling apart when we got to Clark. It appears that luggage was exposed to weather in TPE while waiting to be loaded. Crew, however, handled the delay well and was able to provide planned service.

Sub sandwhich for a snack through mid flight and giving a bottle water was a good idea

Everything is good staff is polite and helpful flights are on time sub sandwhich for a snack was good with a bottle of water only thing maybe more variety of food like breakfast or dinner depends on the time

seats are pitched well. you don't feel too tight.

For the price, it was better than other airlines; quality of food and service was very good.

JAL is an exceptional airline that shows the true heart of Japanese omotenashi service. If the option is available I’ll always chose it

I avoid American Airlines for a reason. Our flight was delayed at LAX. The situation at the gate was chaotic. The woman making announcements wasn't being clear or transparent regarding why there were delays. There was a lot of confusion regarding flight and gate status. Other passengers were pretty rude. I was elbowed in the eye by someone who was in a hurry to get their bags from the overhead bin immediately after the flight landed. Ultimately, I will avoid AA as much as possible in the future.

I love Japan Airlines! I go out of my way to book with them. It is regrettable that the One World Alliance includes American Airlines though. The last leg of my flight from LAX to Austin was easily the worst, most disorganized part of the trip. Next time I will plan to fly directly from DFW to Haneda to avoid American Airlines as much as possible.

Issue 1: We had a 2 hour delay to repair a windshield wiper, during which we sat on board on the runway. Issue 2: it was VERY HOT in the cabin for most of the flight, we were sweating. We asked to make it cooler. They didn’t succeed in doing so. Other than that, it was great. Fantastic food, and extremely pleasant, accommodating flight crew.

We asked for Hindu vegetarian meal in advance and the quality of the food was horrendous. Never flying JAL again!

My total experience was good. The food and entertainment need improvement.

I wish I was able to flew with JAL all the way to DFW. After my JAL flight to Japan it was taken over by a flight with AA which is another experience, the plane was not as roomy like JAL. I was terrified to drop anything in the floor and not have the room to bend and pick it up. My wifi din not work at all, l just slept through majority of the flight. Although not a bad experience, I still wish that I flew JAL straight to DFW for the experience.

I would like to add American food so tired of rice after being there for 10 days didn’t want anymore to pay an airline did not have my bag marked right so it is still sitting in O’Hare. I am home.

Flight from New Delhi to Tokyo was mediocre. The seats were not of business class as we are used to. They were not wide enough. On the other hand the seats on the flight from Tokyo to San Francisco were excellent every thing were great except the food. Tokyo business lounge was excellent. The whole experience was great except the food on the plane. Will still fly JAL.

The entree wasn’t very good. The rice was soggy. The side dishes were all good though. The breakfast was also good. The crew were excellent, as usual.

Check in process at the kiosk, crew in flight and overall comfort was good. Food selection could have been better. Flight from Hong Kong to Los Angeles did not have any vegetarian main course option, it was either sea food or chicken. Being a vegetarian I could only eat yogurt and fruit. Most international flights have one vegetarian main course dish which I found missing in Cathay Pacific menu.

As before, my only problem was not being able to download my boarding passes prior to arrival at the airport. Everything else was perfect.

The only problem I had was not being able to download my boarding passes prior to arriving at the airport. Everything else was perfect.

Better. I took an aisle seat this time. Although the overheard compartment above the seat ahead of me kept opening up during flight.

They ran out of food and were offering random food to passengers.

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

Flight was delayed at the last minute for six hours. Instead of delaying it to a normal hour, they moved it to 10 pm to essentially make it a redeye. There was no compensation or benefit offered for this inconvenience. Once on the plane, Inpaid for WiFi twice with both times it not working because of a “weak WiFi signal”, according to the flight attendants. They also chose the farther possible gates in both airports from the entrance/exit, even though they were one of the few active flights left so late in the evening. Overall it was pretty horrible.

Special request meals are really below average. Vegetarian options are very limited if you didn't prebook.

very professional and very attentive to my Special Needs as I required a Wheel Chair and assistance to board

Very noisy and careless crew on this overnight flight. They should understand customers want to sleep

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Everything you need to know for your flight from Singapore to Chicago

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.