S$ 637 Find Cheap Flights 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 to Chicago departing on 20-11. 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, 0 bags

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 for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Flight Deals

Cheap Flights to Chicago

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

Thu, 20 Nov - Sun, 30 Nov
Air Canada Logo
21:00 - 14:41SIN-ORD
31h 41m2 stops
Air Canada Logo
07:05 - 07:00ORD-SIN
33h 55m2 stops
S$ 1,055Air Canada
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Fri, 28 Nov - Fri, 5 Dec
Air Canada Logo
08:50 - 14:41SIN-ORD
19h 51m1 stop
Air Canada Logo
15:40 - 11:15ORD-SIN
29h 35m2 stops
S$ 1,089Air Canada
Find Deal
Thu, 20 Nov - Mon, 1 Dec
Cathay Pacific Logo
20:15 - 12:55SIN-ORD
30h 40m1 stop
Cathay Pacific Logo
14:35 - 05:40ORD-SIN
25h 05m1 stop
S$ 1,172Cathay Pacific
Find Deal
Fri, 21 Nov - Fri, 28 Nov
Cathay Pacific Logo
07:40 - 12:55SIN-ORD
19h 15m1 stop
Cathay Pacific Logo
14:35 - 05:40ORD-SIN
25h 05m1 stop
S$ 1,184Cathay Pacific
Find Deal
Thu, 16 Apr - Mon, 20 Apr
United Airlines Logo
09:00 - 16:50SIN-ORD
20h 50m1 stop
United Airlines Logo
06:15 - 18:25ORD-SIN
23h 10m1 stop
S$ 1,206United Airlines
Find Deal
Tue, 10 Feb - Fri, 20 Feb
United Airlines Logo
22:20 - 06:25SIN-ORD
22h 05m1 stop
United Airlines Logo
06:25 - 20:15ORD-SIN
23h 50m1 stop
S$ 1,207United Airlines
Find Deal
Wed, 15 Apr - Mon, 20 Apr
Korean Air Logo
01:10 - 09:40SIN-ORD
21h 30m1 stop
Korean Air Logo
12:20 - 05:00ORD-SIN
27h 40m1 stop
S$ 1,233Korean Air
Find Deal
Wed, 15 Apr - Mon, 20 Apr
Korean Air Logo
01:10 - 09:40SIN-ORD
21h 30m1 stop
Korean Air Logo
12:20 - 23:40ORD-SIN
22h 20m1 stop
S$ 1,234Korean Air
Find Deal
Tue, 25 Nov - Sun, 30 Nov
Delta Logo
01:35 - 23:40SIN-MDW
36h 05m2 stops
Delta Logo
18:48 - 00:10MDW-SIN
39h 22m2 stops
S$ 1,238Delta
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Tue, 25 Nov - Tue, 2 Dec
Delta Logo
01:35 - 23:59SIN-ORD
36h 24m2 stops
Delta Logo
07:50 - 05:00ORD-SIN
31h 10m2 stops
S$ 1,238Delta
Find Deal

Everything you should know

When to travel
October
Cheapest • 17% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
S$ 1,055
Overall average: S$ 1,415
Air Canada
Thu 20-11Sun 30-11
SIN - ORD • 2 stops
Cheapest one-way flight
S$ 637
Typical prices: S$ 747-S$ 859
IndiGo
Thu 20-11
SIN - ORD • 2 stops
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for flights to Chicago

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

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights 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 to Chicago is October, where tickets cost S$ 1,190 on average for one-way flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from Singapore is S$ 1,920 and S$ 1,619 respectively. For return trips, the best month to travel is October with an average price of S$ 1,190.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of S$ 257.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightS$ 637
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly (12% more expensive on average)
Flight from Singapore to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel 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. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (14 km). You'll travel 26 km to reach the center of Chicago if you land in Chicago O'Hare Airport and 126 km if you land in Chicago Greater Rockford.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where tickets can be as cheap as S$ 1,540. On the other hand, the most expensive day to fly is Sunday, where prices are S$ 2,277 on average.

  • How does KAYAK find such low prices on flights 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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    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 to Chicago 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 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 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 Chicago?

    The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost S$ 1,479 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is S$ 1,720.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop to Chicago.
Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

Singapore to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Reviews of the top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Singapore to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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 1265 reviews
8.4Boarding
8.0Entertainment
8.6Crew
8.1Food
8.3Comfort
Airline reviews

Its fantastic!!I like the food the serve in EVA air😊

10.0 ExcellentMary Grace, Oct 2025TPE - SEA
Read more EVA Air reviews

Its fantastic!!I like the food the serve in EVA air😊

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

Flight was canceled was only given only a 8 hour lead time. Had to fight to be put on another airline (United Airlines) that was leaving earlier then the one EVA and rescheduled.

Awful had to ask for a supervisor to sit with my flight companion even t booked the tickets together weeks before

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!

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.

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.

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

Great as can be expected with a 10 hour flight over the Pacific. Great movie selection of new releases that hadn’t hit streaming yet. And despite the bad rep, I actually like the airplane good.

One of the best business class seats I’ve had. The lie flat seats made it comfortable to endure a 12 hour flight. Service was excellent and food was great.

Almost 6 hours of delay with over 12 gate changes. Flight was supposed to depart around 6 and instead depart after 12am. No accommodations were offered than some snacks closer to midnight when the crew was planning to throw away some snacks.

Purchased WiFi was slow to non functional. Staff was not personable or friendly. Seats were cramped. Boarding took long but I expected that.

The crew was excellent. The flight was delayed for 20 to 25 minutes. We did arrive a bit later than expected. The AC could have been better.

Very disappointed with the seat selection. During the booking, I selected seats such that my wife and I would sit next to each other. However, during check-in, we found out that the airline changed our seats and we were seated apart; and I was stuck in the middle seat with two strangers. Very disappointing experience. We would not fly ANA next time.

Luckily I just tried to sleep. But the entertainment system was awkward to operate. I hate all this stuff with apps and adding it to your phone and all. It is a nuisance. I would prefer a good magazine or newspaper in the pocket in front of me or available.

Upgrade the comfort, food and attendants. Also we arrived in Houston in the morning. The meal they served two hours before our arrival was a dinner entree. It would have been a lot nicer and much more appropriate to have had breakfast.

During booking, I selected the seats so that my wife and I would sit next to each other. However, the airline changed our seats at boarding so that we were seated apart. Very disappointing.

Wonderful I would recommend it to fly & ride with ANA.

The seat was uncomfortable and seemed to be on its last days. Loose and sloppy

Business class lie flat seat is the best and easiest to operate 👍👍

My seat had zero leg room. I thought I was flying Japan Airlines, a company I picked based solely on the legroom... When I got to the airport on my first flight, they informed me that I was in fact flying J.A.L VIA American Airlines... What a bait and switch. I will never fly AA on an international flight ever again.

put me in front row, screen was tiny, movie slection wasnt very good will be flying back on another airlines

Excellent flight. Check in experience was a breeze. Smooth and on time flight. Friendly and attentive attendants. Premium economy seating was very spacious. The lounges in both SEATAC and Narita were first rate. The only negative was the inflight food and entertainment options, which were limited, and Wi-Fi was not working. We would definitely fly JAL again.

Not good. The flight from LAX to Tokyo was delayed 15 hours.

My luggage is missing and waiting to hear back about it. 3 of my 6 checked bags didn’t make it to DFW.

Boarding, crew, and seating were great. The food needs to improve.

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.

Leg room wasn't that great. Other than that it was a good flight

Issues: 1) the charging issue as described in my previous survey 2) when I requested diet coke during the breakfast time, it is not available. Why? I can't drink diet coke in the morning? 3) when I tried to transfer to this flight, its gate information was not available to me?

The lead business class attendant was excellent. Made a point of greeting you and knowing your name by the time you leave.

A lot of things Never flying with this airline again Had an emergency landing

Chicken pieces were too big with pasta. Need to be smaller.

Overall pretty good experience. It would be nice to have caught the attendants even they were flying down the aisle with snacks, and if they could cater to multiple dietary restrictions (bland and no lactose. The customer service chat is a bad experience), but otherwise no complaints.

I am Vegetarian also has Gluten free food. However they gave me chicken and fish which is gluten free, but i am a vegetrain and i requested crew Hindu meal vegetarian, they said they will come back. .but they never showed up even i asked 2nd time. They could have compensate. I also request airline industry to have another option Gluten Free for Vegetarin people as well. Because Vegetarin people will have gluen issue...

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

Just want to do a little more clean up so does not smell like urine.

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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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