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 12-5. 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

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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Flights Deals

Cheap Flight Deals 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.

Recent return flight deals to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
 Logo
15:10 - 05:40SIN-ORD
27h 30m2 stops
 Logo
20:42 - 12:00ORD-SIN
26h 18m2 stops
S$ 1,335
Find Deal
Tue, 24 Jun - Wed, 23 Jul
 Logo
15:10 - 05:40SIN-ORD
27h 30m2 stops
 Logo
20:42 - 12:00ORD-SIN
26h 18m2 stops
S$ 1,339
Find Deal
Mon, 23 Jun - Mon, 30 Jun
Cathay Pacific Logo
20:05 - 14:25SIN-ORD
31h 20m1 stop
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
S$ 1,453Cathay Pacific
Find Deal
Tue, 24 Jun - Wed, 23 Jul
Japan Airlines Logo
01:55 - 09:15SIN-ORD
20h 20m1 stop
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
S$ 1,478Japan Airlines
Find Deal
Mon, 23 Jun - Tue, 22 Jul
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
16:00 - 12:25ORD-SIN
31h 25m1 stop
S$ 1,480Cathay Pacific
Find Deal
Tue, 24 Jun - Mon, 7 Jul
Japan Airlines Logo
01:55 - 09:15SIN-ORD
20h 20m1 stop
Japan Airlines Logo
12:30 - 00:20ORD-SIN
22h 50m1 stop
S$ 1,483Japan Airlines
Find Deal
Mon, 23 Jun - Wed, 23 Jul
EVA Air Logo
15:10 - 05:40SIN-ORD
27h 30m2 stops
EVA Air Logo
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,511EVA Air
Find Deal
Wed, 25 Jun - Sun, 6 Jul
United Airlines Logo
08:45 - 05:29SIN-ORD
33h 44m1 stop
United Airlines Logo
06:30 - 18:25ORD-SIN
22h 55m1 stop
S$ 1,658United Airlines
Find Deal
Wed, 25 Jun - Mon, 7 Jul
EVA Air Logo
13:10 - 21:00SIN-ORD
20h 50m1 stop
EVA Air Logo
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,755EVA Air
Find Deal
Sat, 21 Jun - Fri, 27 Jun
United Airlines Logo
08:45 - 00:45SIN-ORD
29h 00m1 stop
United Airlines Logo
08:45 - 06:40ORD-SIN
32h 55m2 stops
S$ 5,668United Airlines
Find Deal
Thu, 4 Sep - Fri, 19 Sep
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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 day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as S$ 1,560. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,308 on average.

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 February, where tickets cost S$ 1,318 on average for return flights. On the other hand, the most expensive months are August and January, where the average cost of tickets from Singapore is S$ 1,948 and S$ 1,898 respectively. For one-way flights, the best month to travel is February with an average price of S$ 1,318.

What is the cheapest time of day to fly to Chicago?

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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.

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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 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 O'Hare Intl Airport (ORD), with an average flight price of S$ 780.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

High season

June

Cheapest flight

S$ 637
Best time to beat the crowds but there is an average 19% 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.

  • 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.

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?

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, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Top 4 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 1186 reviews
8.3Comfort
8.1Food
8.4Boarding
8.0Entertainment
8.6Crew
Airline reviews

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.

10.0 ExcellentDale, Apr 2025TPE - CRK
Read more EVA Air reviews

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.

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

Excellent food. Good service. Crammed Premium Economy seats. I Asked to change seats during check in. They told me the flight was fully booked. But on board I saw empty seats where I could have been easily relocated.

delayed and the cabin crew was like trainees.. a bit careless and not so pleasing to their job

Except for crying babies all was ok although the movie selection wasn't the best.

The staff was marvelous. The entertainment options were terrible, old or 2nd rate movies. I was unable to entertain myself for 18 hours-it made it seem even longer. Note: I thought about upgrading but your information about what was included was unclear. Are the seats bigger? Are there current moves? What kind of food do you get? Would the upgrade compare to Delta? Just saying the upgrade is better didn’t convince me and I regret not flying Delta.

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.

The flight attendants were excellent as usual however the meal wasn’t the usual good quality. There is cooked rice was mushy.

This portion of the trip from HCMC to Dallas was operated by American Airline. Unfortunately they are 2 steps below JAL in overall quality. Regardless, AAStill got me where I needed to go on time.

Website from the 1990s, super frustrating customer support, inflight experience merely OK - more like United than e.g. Emirates

The seats are significantly more comfortable than US airlines and the staff are much friendlier. The food is also much better, as they are particularly accommodating to any dietary restrictions.

Could had been better if they include in their menu some western food.

They 7 seats in one row for Business class while most business class for other airlines are 4 seats in one row. the seat was narrow. the Toilet was so smell, dimming light, no water out of faucet. Terrible.

Difficult to access advanced check-in online. No way to understand why it wouldn’t work. Call center not answering. Email for answers took days to respond, Kind service at the airport and on the flight made up for disappointing service before flight.

Courteous and helpful employees. Comfortable seats and temperature of aircraft . Did not need squid in my salad but glad to have the menu information advising me of what it was

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

Crew was great. But a bit understaffed. The business class seat, etc were dated. But comfortable. Some legs had entertainment system from a decade ago. Selections were rather poor. Food was mediocre at best. Actually poor for business class standards. I liked the lounge in Hong Kong. Showers were great. Food was nice.

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

It was okay overall but the food was very, very bad.

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

Baggage delayed for 2 days and still chasing for reimbursement of basis items. Very horrible customer care service.

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.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

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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