S$ 669 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 15-10. 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 for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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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

Sat, 31 Jan - Mon, 16 Feb
Air Canada Logo
08:50 - 14:41SIN-ORD
19h 51m1 stop
Air Canada Logo
20:15 - 07:00ORD-SIN
44h 45m2 stops
S$ 1,016Air Canada
Find Deal
Sun, 1 Feb - Tue, 17 Feb
Air Canada Logo
22:20 - 19:30SIN-ORD
35h 10m2 stops
Air Canada Logo
07:15 - 00:55ORD-SIN
27h 40m2 stops
S$ 1,021Air Canada
Find Deal
Sat, 13 Sep - Sun, 21 Sep
 Logo
00:20 - 22:43SIN-ORD
35h 23m2 stops
 Logo
06:30 - 23:20ORD-SIN
27h 50m2 stops
S$ 1,039
Find Deal
Sat, 31 Jan - Mon, 16 Feb
Air Canada Logo
06:35 - 19:30SIN-ORD
26h 55m2 stops
Air Canada Logo
20:15 - 07:00ORD-SIN
44h 45m2 stops
S$ 1,041Air Canada
Find Deal
Fri, 30 Jan - Sun, 15 Feb
Air Canada Logo
08:50 - 14:41SIN-ORD
19h 51m1 stop
Air Canada Logo
15:40 - 07:00ORD-SIN
25h 20m1 stop
S$ 1,042Air Canada
Find Deal
Tue, 30 Sep - Tue, 7 Oct
ANA Logo
06:15 - 14:55SIN-ORD
21h 40m1 stop
ANA Logo
17:45 - 06:40ORD-SIN
23h 55m1 stop
S$ 1,051ANA
Find Deal
Sat, 13 Sep - Sun, 28 Sep
 Logo
00:20 - 22:43SIN-ORD
35h 23m2 stops
 Logo
06:30 - 23:20ORD-SIN
27h 50m2 stops
S$ 1,052
Find Deal
Tue, 23 Sep - Mon, 29 Sep
ANA Logo
06:15 - 14:55SIN-ORD
21h 40m1 stop
ANA Logo
11:50 - 00:45ORD-SIN
23h 55m1 stop
S$ 1,057ANA
Find Deal
Mon, 29 Sep - Tue, 7 Oct
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
S$ 1,223Cathay Pacific
Find Deal
Tue, 16 Sep - Wed, 1 Oct
United Airlines Logo
08:45 - 05:23SIN-ORD
33h 38m1 stop
United Airlines Logo
06:15 - 18:25ORD-SIN
23h 10m1 stop
S$ 1,231United Airlines
Find Deal
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$ 1,163 on average for return flights. On the other hand, the most expensive months are January and August, where the average cost of tickets from Singapore is S$ 1,855 and S$ 1,599 respectively. For one-way flights, the best month to travel is October with an average price of S$ 1,163.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights 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, you should book around 2 weeks before departure, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

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 (MDW), with an average flight price of S$ 254.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightS$ 669
Best time to beat the crowds but there is an average 29% increase in price.
Most popular time to fly (6% 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 round-trip tickets can be as cheap as S$ 1,526. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,257 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 round-trip flights cost S$ 1,142 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$ 1,328.

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, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +73 more

ANA, Aer Lingus, +74 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +73 more

ANA, Aer Lingus, +74 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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 1232 reviews
8.3Comfort
8.0Entertainment
8.4Boarding
8.1Food
8.6Crew
Airline reviews

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

4.0 OkayAnonymous, Aug 2025TPE - SEA
Read more EVA Air reviews

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

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.

Movie selection was not as good as recent flights I've taken (EVA and other airlines).

Great but I am not sure why I was placed in zone 4 for boarding despite being an Infinity Member??? Can you explain online. Thanks

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.

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.

I have a Peanut Allergy and the Steward staff were very accommodating in ensuring my safety as my allergy is life threatening. Very professional and so vested in their profession.

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

Everything was fine and I have no complaints or things to note.

The flight was delayed for 30 mins. The overall experience was good.

Highly impressive. On time. Smooth and fast boarding and disembarkment. Really great service

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

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.

Could not understand what the attendant was saying during his announcements.

Biggest problem for me is that I am Star Alliance Gold and they were not able to give me access to to Maple Lounge because of some computer glitch . It was management by information system. She could clearly see my status and still would not give me access because the computer woudl not let her. She should have override that be attentive to a customer and figure rhat out later

Economy seats always cramped, no meal on international flight, no plugs for electronics, but we got there and cabin crew was excellent.

Horrible, experience, 5 hours delay, they changed gates 3 times, the last one we had to wait for 1::30 hre for the door to open to get to that gate. 0 apologies from Air Canada, they don’t care at all about their passengers

I paid for comfort plus seats but did not get the extra leg room. When I told the stewardess, she just ignored me.

Great breakfast and coffee …..fastest bag service I have ever had in NOLA

I had a very disappointing experience with customer service. I was suffering from a severe viral infection that included a rash and persistent cough, leaving me unable to even sit upright. Given the circumstances, I requested travel credits from Canada Air, explaining the potential health risk to others onboard. However, the airline showed no concern for my condition and stated they were not in a position to make decisions based on health considerations. Despite my illness, I received no support or flexibility. Ultimately, I chose to forgo my flight due to their lack of responsiveness. It’s unfortunate that airlines like this operate without prioritizing passenger health and safety.

Late departing. Late arriving. More worried about limiting bags on board. Free beer and wine a nice surprise.

I did not noticed baggage was separate - I had assumed international flights included luggage, so it surprised me I had to pay to check a bag.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

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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