S$ 665 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 20-8. 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, 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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Everything you should know

Cheapest return fare
S$ 1,042
Typical prices: S$ 1,683-S$ 1,448
Air Canada
Tue 16-6Sat 20-6
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 665
Typical prices: S$ 765-S$ 1,849
Air Canada
Thu 20-8
SIN - ORD • 2 stops
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
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

Tue, 16 Jun - Sat, 20 Jun
Air Canada Logo
07:00 - 14:45
SIN
-
ORD
20h 45m
1 stop
Air Canada Logo
21:54 - 05:15
ORD
-
SIN
42h 21m
2 stops
S$ 1,042Air Canada
Wed, 8 Jul - Wed, 15 Jul
United Airlines Logo
06:15 - 00:59
SIN
-
ORD
31h 44m
2 stops
United Airlines Logo
07:10 - 00:45
ORD
-
SIN
28h 35m
2 stops
S$ 1,201United Airlines
Sun, 25 Oct - Mon, 9 Nov
Korean Air Logo
07:30 - 09:30
SIN
-
ORD
39h 00m
1 stop
Korean Air Logo
11:15 - 20:25
ORD
-
SIN
43h 10m
1 stop
S$ 1,221Korean Air
Thu, 22 Oct - Sun, 25 Oct
Korean Air Logo
01:25 - 09:30
SIN
-
ORD
21h 05m
1 stop
Korean Air Logo
12:15 - 05:00
ORD
-
SIN
27h 45m
1 stop
S$ 1,222Korean Air
Sat, 24 Oct - Sun, 8 Nov
Air Canada Logo
07:00 - 19:53
SIN
-
ORD
25h 53m
1 stop
Air Canada Logo
15:40 - 07:00
ORD
-
SIN
25h 20m
1 stop
S$ 1,327Air Canada
Thu, 22 Oct - Sat, 7 Nov
Multiple Airlines Logo
01:25 - 09:30
SIN
-
ORD
21h 05m
1 stop
Multiple Airlines Logo
11:15 - 21:55
ORD
-
SIN
44h 40m
1 stop
S$ 1,359Multiple Airlines
Sat, 24 Oct - Sun, 8 Nov
Delta Logo
07:30 - 23:46
SIN
-
ORD
29h 16m
2 stops
Delta Logo
11:15 - 00:10
ORD
-
SIN
22h 55m
1 stop
S$ 1,364Delta
Sun, 26 Jul - Fri, 21 Aug
Malaysia Airlines Logo
11:05 - 07:45
SIN
-
ORD
33h 40m
2 stops
Malaysia Airlines Logo
10:40 - 10:15
ORD
-
SIN
34h 35m
2 stops
S$ 1,374Malaysia Airlines
Tue, 16 Jun - Mon, 6 Jul
Malaysia Airlines Logo
21:15 - 07:45
SIN
-
ORD
23h 30m
2 stops
Malaysia Airlines Logo
10:40 - 20:25
ORD
-
SIN
44h 45m
2 stops
S$ 1,384Malaysia Airlines
Wed, 17 Jun - Tue, 7 Jul
Delta Logo
07:30 - 23:39
SIN
-
ORD
29h 09m
2 stops
Delta Logo
20:21 - 23:55
ORD
-
SIN
38h 34m
2 stops
S$ 1,422Delta
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 February, where tickets cost S$ 936 on average for return flights. On the other hand, the most expensive months are January and June, where the average cost of tickets from Singapore is S$ 1,810 and S$ 1,575 respectively. For one-way flights, the best month to travel is February with an average price of S$ 936.

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$ 270.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonFebruary
Cheapest flightS$ 665
Best time to beat the crowds (31% less expensive on average)
Most popular time to fly (17% 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.

Reviews of the top 3 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.
8.5
EVA AirOverall score based on 1445 reviews
8.3Comfort
8.4Boarding
8.6Crew
8.0Entertainment
8.1Food
Airline reviews

Other than spotty internet, great servic, comfortable and smooth flight!

8.0 ExcellentDror, Apr 2026
TPE - JFK
Read more EVA Air reviews

Other than spotty internet, great servic, comfortable and smooth flight!

Crew was good. Sometimes food was eh. The spaghetti is gross for me. First time i got food, they didn’t provide utensils so i ate with my hands. I was hungry. They gave it to me 20 mins later when a crew member came by. I would fly with them again. Nobody is perfect

Eva air was fine - Trip.com via KAYAK sold my family access to a “VIP” lounge fo a layover in Taipei… i’m please look at my pictures. It was a scam, Trip.com knows it and they are perpetrating a fraud through your web site.

My flight was amazing smooth and the attendants were so friendly and nice

Organized boarding process, superb food, lovely crew, even arrived early!

Crew are excellent. Food was good generally. Seats are small and there isn’t much leg room. Overhead bins are very small.

What could have been better, was we were delayed from takeoff for two hours. Initially we were informed that we were delayed for refueling. Then we taxied out on the tarmac, then just waited there for a long time, with no explanation of the delay. Were we just waiting on takeoff clearance or was there some other reason for the delay? The pilot, nor none of the crew informed us passengers. That was not good customer service. That needs to be improved, whenever a delay, inform the passengers for the reason.

More seat space More bathrooms Charging outlets Plane was old

This flight was long and I am so thankful I had a seat in the back of the plane. As I usually must get up and stretch every hour . The crew were probably the most friendly I have flown with. Thanks and I will book again with Eva air. Food was ok too.

It was a pleasure to fly with EVA airlines from Taipei to San Francisco.

I paid for premium and it’s wasn’t what I was told I would be getting. Food wasn’t good. Should be able to pick and not be served items you dislike. Very little leg room.

I am trying to select a seat during booking but it respond that set assigment will be given during check in, and the seat assignment they give is in the middle seat and 2 row from the rest rooms, i am the person who pee a lot in this case I disturb so much the person beside me ,this trip is from Haneda to Texas, the trip from Texas to Cvg is a much better because its a smaller plane few passenger

Their in0flight movie selection is limited in size and poor in quality.

Japan airlines is a great airline. One of my favorites. The only issue I had was that I only pescatarian or I can eat vegetables, pasta, etc and both choices of meals were chicken or red meat. Most of other airlines have meat or pasta. Also usually I get an alert to order a meal prior to fly and this time I did not get one. Other than that everything was wonderful.

Boarding and crew service were excellent. Food was mediocre, not as good as our last trip four years ago.

Great level of comfort and highly professional and friendly flight crew. Keep up the great service.

It was amazing. Japan is lovely. I hope to go again. Thank you for everything.

My first issue is the lack of clarity with the airlines. I know that Japan airlines and American Airlines are partners, but I couldn’t figure out which airline I was flying with. I got the flight info for Japan airlines and ended up on American. After my Kayak booking (via Underpricer) I got a phone call to see if I wanted up choose a seat and pay for luggage fees. both American and Japan airlines offer 2 carryons and 2 regular luggage checked in at no additional fees to Tokyo. Having already done my research, I opted out on their “Offer” and just contacted the airline directly to pay for upgraded seats (Which were cheaper than the Underpricer deal) My top complaint was the flight delay from HND to LAX it wasn’t until I had already made my unchangable airport drop off car reservations , that I received 3 hour flight delay email. I was forced to be there 6 hours prior to the departure. They were kind enough to give us a limited restaurant food voucher- which was 1900 yen ( I saw Delta food vouchers were 2000 yen). My teen and I ate food court pizza. The flight arrived when expected, The food was mid on the flight. I slept and woke up about 1.5 hours to LAX. I had waffles ( which also contained 1 mushroom and 1 tomato in the same tray) and 3 small pieces of fruit. All went well, just remember to check on your 3rd party ticket companies. Some seem to be sneaky All in all it was a very long day, we made it back safe.

Horrible like always, flight was supposed to be at 11:40am, we ended up getting a different airplane at 3:25pm.

I have been flying with JAL a few times, crews service, food, overall comfort even with economy, I would rate it the top three airlines. None of any American carriers can provide such excellent service.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

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.