S$ 566 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return fare
S$ 954
Typical prices: S$ 886-S$ 1,359
Air Canada
Sat 3-10Sun 18-10
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 566
Typical prices: S$ 737-S$ 810
Air Canada
Thu 26-11
SIN - ORD • 1 stop
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Cheap Flights to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Sat, 3 Oct - Sun, 18 Oct
Air Canada Logo
07:00 - 14:43SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 43m1 stop Vancouver Intl
Air Canada Logo
08:49 - 05:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
31h 26m1 stop Vancouver Intl
S$ 954Air Canada
Thu, 15 Oct - Wed, 28 Oct
Air Canada Logo
07:00 - 14:43SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 43m1 stop Vancouver Intl
Air Canada Logo
08:40 - 07:00ORD  Chicago O'Hare Intl-SIN Singapore Changi
33h 20m2 stops Calgary Vancouver Intl
S$ 974Air Canada
Sun, 11 Oct - Sun, 18 Oct
Air Canada Logo
07:00 - 14:43SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 43m1 stop Vancouver Intl
Air Canada Logo
15:40 - 05:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
24h 35m1 stop Vancouver Intl
S$ 975Air Canada
Thu, 15 Oct - Wed, 28 Oct
Air Canada Logo
07:00 - 20:06SIN  Singapore Changi-ORD Chicago O'Hare Intl
26h 06m1 stop Vancouver Intl
Air Canada Logo
08:49 - 07:00ORD  Chicago O'Hare Intl-SIN Singapore Changi
33h 11m1 stop Vancouver Intl
S$ 975Air Canada
Wed, 9 Sep - Sat, 12 Sep
United Airlines Logo
08:45 - 20:26SIN  Singapore Changi-ORD Chicago O'Hare Intl
24h 41m1 stop San Francisco
United Airlines Logo
21:40 - 18:35ORD  Chicago O'Hare Intl-SIN Singapore Changi
31h 55m1 stop San Francisco
S$ 1,420United Airlines
Sat, 26 Dec - Thu, 31 Dec
EVA Air Logo
15:45 - 19:35SIN  Singapore Changi-ORD Chicago O'Hare Intl
41h 50m1 stop Taipei City Taiwan Taoyuan Intl
EVA Air Logo
23:30 - 12:05ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 35m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,636EVA Air
Mon, 11 Jan - Mon, 11 Jan
United Airlines Logo
10:45 - 20:22SIN  Singapore Changi-ORD Chicago O'Hare Intl
23h 37m2 stops Tokyo Haneda Los Angeles
United Airlines Logo
23:00 - 23:40ORD  Chicago O'Hare Intl-SIN Singapore Changi
34h 40m2 stops Los Angeles Tokyo Narita
S$ 1,640United Airlines
Mon, 11 Jan - Mon, 11 Jan
United Airlines Logo
06:35 - 13:50SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 15m1 stop Tokyo Narita
United Airlines Logo
20:01 - 00:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
38h 54m2 stops San Francisco Tokyo Narita
S$ 1,641United Airlines
Wed, 23 Dec - Thu, 24 Dec
EVA Air Logo
13:15 - 19:35SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 20m1 stop Taipei City Taiwan Taoyuan Intl
EVA Air Logo
16:07 - 12:05ORD  Chicago O'Hare Intl-SIN Singapore Changi
29h 58m2 stops Seattle/Tacoma Intl Taipei City Taiwan Taoyuan Intl
S$ 1,688EVA Air
Wed, 23 Dec - Thu, 24 Dec
EVA Air Logo
13:15 - 06:40SIN  Singapore Changi-ORD Chicago O'Hare Intl
31h 25m2 stops Taipei City Taiwan Taoyuan Intl Seattle/Tacoma Intl
EVA Air Logo
16:07 - 12:05ORD  Chicago O'Hare Intl-SIN Singapore Changi
29h 58m2 stops Seattle/Tacoma Intl Taipei City Taiwan Taoyuan Intl
S$ 1,810EVA Air
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.

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$ 290.

Good to know – Book Cheap Chicago Plane Tickets

Low season

September

Cheapest flight

S$ 566
Best time to beat the crowds (28% less expensive on average)
Most popular time to fly (75% 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

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 4 airlines flying to Chicago

 
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 1522 reviews
8.5Boarding
8.0Entertainment
8.3Comfort
8.7Crew
8.1Food
Airline reviews

First international flight where the meals were not to my taste.

8.0 ExcellentIvonny, Jul 2026
Read more EVA Air reviews

First international flight where the meals were not to my taste.

Overall, my experience with EVA Air was mixed. The highlight was that the airline clearly tried to provide a premium dining experience by offering the Michelin-starred Kanpai Classic beef yakiniku rice. However, in the limited space of an economy-class cabin, this meal felt overly oily and not very practical to eat. The sauce and grease made it easy to get one’s hands or tray table dirty, and after the meal many passengers may need to go to the lavatory simply to wash their hands. While the food itself may be high quality, the presentation and practicality did not seem well suited to an in-flight environment. Another disappointing part was the paid Wi-Fi service. I paid for the internet package, but the service did not work properly. What made the experience more frustrating was that passengers then had to spend additional time requesting a refund, and the refund process itself was slow and inconvenient. For an international airline, I think a malfunctioning paid service should be handled more efficiently. As for the seat, I feel EVA Air’s economy-class seats may be more comfortable for Asian passengers or people with smaller body frames, but they may not be as comfortable for taller or larger Western passengers on long-haul flights. The overall cabin environment also varied during the flight. Some passengers were not very mindful of noise, cleanliness, or shared cabin etiquette, which affected the comfort of the journey. I believe clearer reminders from the airline regarding cabin manners and hygiene could help improve the overall passenger experience. In short, EVA Air has some strong points, especially in trying to offer a premium Taiwanese-style service, but there are also areas that need improvement: more practical in-flight meals, a more reliable paid Wi-Fi system, faster refund handling, and better cabin management during long-haul flights.

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.

Eva airlines has very goin service, despite being low cost. Meals and fin, not amazing, restrooms always clean and staff polite and helpful

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Polite hard working crew. No complaints really. Meals were not to my liking.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

The business class is excellent. I loved the food, and the crew was very attentive and professional. From boarding to arrival, everything felt smooth and well-organised.

AAAAHHHH... It was shocking in a very positive way, the attention to detail, the courtesy, the manners of all personnel on board, the constant honest smiling. You can see and feel they take pride in all they do no matter how trivial. The plane in general was very comfortable. I can't wait to do it again

Great service and comfort level. You can have more of vegetarian food options.

It’s great, long flight and arrive safe at destination

Everything was excellent as I expected. They also had a very caring crew. I had a headache and asked a Tylenol. The crew members kept checking with me how I was doing.

They were trying to get people to check luggage because the over head compartments were full but when we boarded there were lots of empty places that people could have put the luggage.

I can't believe they put my wife and I in the two middle seats! It is a very long flight and we had single flyers on either side of us blocking the way to the bathroom! There's no reason to not give one of us the isle seat so we could have managed bathroom needs and snacks with convenience. So I think very poorly of Korean air to put us both in the middle, I've never had that happen before and will probably avoid this airline in the future because of this. We tried to have them change it but they didn't so you pretty much lost a customer because of it.

One of the flight attendants stepped on my foot. I was on the aisle seat. A lady inside needed to get out. So Instood. Just then, a flight attentendant came wuicklybtheoughbthe aisle and stepprd on my sock covered toes. I let out a small sound. She stopped momentarily, but didn’t ask how I was just took off of the aisle. Never came back to see how I was. Fortunately, I was not really hurt other than a slight soreness in my toes. But I found that to be very negligent.

Korean Air is unlike any other major airline I have flown with. The grace and respect that the staff has from check in to de-boarding is unmatched. The flight attendants this time were especially wonderful to my five little children. They helped us rearrange to more suitable seating, brought our children’s meals, and patiently waited for them in the aisles when they had to use the bathroom. We felt so welcome and comfortable. I really appreciate the meal voucher when our flight was delayed. I am grateful to have had such an stress-free experience.

Not very comfortable seated in the back plane due to turbulence

I always enjoy flying with Japanese Airlines. The whole experience is always a pleasure. This flight was no exception. Thank you Kayak for making it so easy to decide.

Overall, it was ok. The attendants are nice. It was a short flight, and I did not use the restrooms. What I was frustrated was the check-in. I was to fly from ATL to Chicago (American) then change to Japan Airline to go to Japan. I checked in, but I only got a boarding pass for the flight from Atlanta to Chicago. It said I would need to check in for a flight to Japan on Japan Airline site. When I tried to check in on JAL website, it said I need to check in American... It was very confusing.

service was excellent. crew very polite, courteous, and good service especially to passengers like me who is a wheelchair passenger

The flights were on time and the cabin crew were very nice. The only downside was that the food was not good

Very comfortab flight. The flight crew and service was terrific. The food was average at best.

Excellent service, excellent food and beverage options, plenty of legroom

Check in procedure is harder than with other airlines, infotainment system is outdated

great experience - staff were kind and attentive and food was excellent. very comfortable flight that felt much shorter than 14 hours.

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 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.

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago