S$ 634 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
S$ 1,008
Typical prices: S$ 1,372-S$ 2,181
Air Canada
Mon 12-11Sun 25-11
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 634
Typical prices: S$ 755-S$ 1,131
Air Canada
Mon 12-11
SIN - ORD • 1 stop
Top airlines
Best reviews • 8.5 score
Airline reviews
Airline reviews
When to book
in advance
Our data shows that travellers who book at least 23 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
+1
Good to know
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We hope you enjoy your trip to Chicago!
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Booking Insights
Flight Deals

Cheap Flights to Chicago

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

Recent return flight deals to Chicago

Thu, 12 Nov - Wed, 25 Nov
Air Canada Logo
08:40 - 14:37SIN  Singapore Changi-ORD Chicago O'Hare Intl
19h 57m1 stop Vancouver Intl
Air Canada Logo
15:30 - 07:00ORD  Chicago O'Hare Intl-SIN Singapore Changi
25h 30m1 stop Vancouver Intl
S$ 1,008Air Canada
Thu, 12 Nov - Wed, 25 Nov
Air Canada Logo
08:40 - 14:37SIN  Singapore Changi-ORD Chicago O'Hare Intl
19h 57m1 stop Vancouver Intl
Air Canada Logo
07:05 - 00:45ORD  Chicago O'Hare Intl-SIN Singapore Changi
27h 40m2 stops Montreal Pierre Elliott Trudeau Intl Tokyo Narita
S$ 1,022Air Canada
Thu, 11 Feb - Fri, 26 Feb
Korean Air Logo
01:40 - 08:30SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 50m1 stop Incheon Intl
Korean Air Logo
11:10 - 05:00ORD  Chicago O'Hare Intl-SIN Singapore Changi
27h 50m1 stop Incheon Intl
S$ 1,050Korean Air
Wed, 4 Nov - Sun, 8 Nov
Japan Airlines Logo
02:20 - 10:00SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 40m1 stop Tokyo Haneda
Japan Airlines Logo
13:30 - 06:40ORD  Chicago O'Hare Intl-SIN Singapore Changi
27h 10m1 stop Tokyo Haneda
S$ 1,054Japan Airlines
Sun, 8 Nov - Wed, 11 Nov
United Airlines Logo
22:20 - 05:47SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 27m1 stop San Francisco
United Airlines Logo
06:00 - 20:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
24h 15m1 stop San Francisco
S$ 1,458United Airlines
Sun, 8 Nov - Wed, 11 Nov
United Airlines Logo
22:20 - 05:47SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 27m1 stop San Francisco
United Airlines Logo
06:00 - 20:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
24h 15m1 stop San Francisco
S$ 1,469United Airlines
Fri, 6 Nov - Mon, 9 Nov
United Airlines Logo
10:10 - 18:49SIN  Singapore Changi-ORD Chicago O'Hare Intl
22h 39m1 stop San Francisco
United Airlines Logo
06:00 - 20:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
24h 15m1 stop San Francisco
S$ 1,498United Airlines
Sat, 13 Mar - Fri, 14 May
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
00:30 - 11:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 25m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,720EVA Air
Mon, 15 Mar - Fri, 14 May
EVA Air Logo
15:45 - 20:35SIN  Singapore Changi-ORD Chicago O'Hare Intl
41h 50m1 stop Taipei City Taiwan Taoyuan Intl
EVA Air Logo
00:30 - 11:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 25m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,720EVA Air
Sun, 14 Mar - Fri, 14 May
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
00:30 - 11:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 25m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,720EVA Air
Booking Insights

Price, demand, and travel trends for flights to Chicago

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What is the cheapest flight to Chicago?

Singapore to Chicago is the cheapest route at S$ 1,008 return, found in the past 5 days on KAYAK. KAYAK data shows this is also the most popular route.

How much is a flight to Chicago?

On average, a return flight from Singapore to Chicago costs S$ 1,630, based on KAYAK data over the past 12 months. Return fares from Singapore average S$ 1,630.

What is the cheapest day to fly to Chicago?

Thursday is the cheapest day to fly to Chicago at S$ 1,404 return on average over the past 12 months on KAYAK. Wednesday is the most expensive at S$ 2,594.

What is the cheapest month to fly to Chicago?

•February is the cheapest month to fly to Chicago with an average price of S$ 1,201 return.
•August (S$ 2,621) and July (S$ 1,703) are the most expensive.

Based on KAYAK data over the past 12 months.

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

Morning flights to Chicago are the cheapest at S$ 1,394 return on average. Night flights are the most expensive at S$ 2,115.

What is a good deal for flights to Chicago?

Flights under S$ 1,372 are considered a good deal. 25% of KAYAK users found return flights to Chicago at or below these prices, with the lowest fares from:
•Singapore S$ 1,372.

When are flights to Chicago the cheapest?

Flights to Chicago are cheapest 23 weeks before departure. Booking in this window typically costs about 45% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for flights to Chicago

Low season

October

Cheapest flight

S$ 634
Beat the crowds with an average 60% drop in travellers.
The most popular month to fly with an average 109% increase in travellers.
One-way flight from Singapore to Chicago O'Hare Intl 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

Your questions about flights to Chicago, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Chicago is a good deal?

    A good deal on a flight to Chicago is around S$ 1,372 return. This fare is in the lowest 25% of return flight prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • Which airports serve Chicago?

    Flights to Chicago arrive at: Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • How expensive are last-minute flights to Chicago?

    Last-minute fares to Chicago (booked within two weeks of departure) are typically 18% higher than the average return fare of S$ 1,630.

  • What is the difference between the most popular and the most frequent airline at Chicago?

    United Airlines operates the most flights from Singapore to Chicago at 0 per week, while Etihad Airways is the airline most often selected by KAYAK users searching for flights from Singapore to Chicago. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80.5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

Your guide to booking Chicago flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For the best chance at a low fare to Chicago, book around 23 weeks before departure. Based on KAYAK data from the last 12 months, fares are historically about 45% lower during this window than last-minute fares.
  • For flights to Chicago, a good return fare is around S$ 1,372. If you find a fare below that, you're getting a strong deal.
  • If your travel dates are flexible, consider flying to Chicago in February. Return fares historically average S$ 1,201, making February the cheapest month to travel based on KAYAK data from the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to morning to save up to S$ 721 on a return flight. Morning flights to Chicago average S$ 1,394 compared to S$ 2,115 for evening flights.
  • Once you arrive in Chicago, a great place to start is Grant Park. It is popular with first-time visitors and can give you a good feel for the area.

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 1551 reviews
8.7Crew
8.1Food
8.0Entertainment
8.4Boarding
8.3Comfort
Airline reviews

Picked our seats when we purchased this flight (2 seats alone on the right) but were assigned two middle seats in the middle row at the gate. Very disappointing for a 10 hour+ flight, and what is the point of picking and paying for seats ahead of time when they just reassign us?

6.0 GoodScott, Sept 2026
Read more EVA Air reviews

Picked our seats when we purchased this flight (2 seats alone on the right) but were assigned two middle seats in the middle row at the gate. Very disappointing for a 10 hour+ flight, and what is the point of picking and paying for seats ahead of time when they just reassign us?

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 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

It was smooth and quiet both ways. Staff was attentive and very friendly.

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

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

The first leg of my trip the Republic Airlines aircraft was late due to a maintenance problem. Then I called United to reroute. Their reroute airline lost my bag but found it and returned it two days later. Hopefully my return trip home is better.

There was not even a single time where united airlines from lga has made to the gate straight , 1 hr if delay today

Flight from Munich to O’Hare was great but it was on Lufthansa, a UA partner. It had more legroom than United, seat slid forward to make reclining more comfortable, they offered free drinks. United offered none of this. Oh and the food was superior to United’s which honestly, sucked.

Requested for warm or hot water because of throat pain, it was denied. The entertainment system was hung, requested the crew to turn it off, instead of turning it off they rebooted the device. It was stuck again, no one bothered to check.

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