S$ 613 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 13-11. 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$ 1,044
Typical prices: S$ 945-S$ 1,668
Air Canada
Sun 18-10Sun 25-10
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 613
Typical prices: S$ 750-S$ 825
Air Canada
Fri 13-11
SIN - ORD • 1 stop
When to travel
Cheapest • 17% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Sun, 18 Oct - Sun, 25 Oct
Air Canada Logo
07:00 - 14:43
SIN
-
ORD
20h 43m
1 stop
Air Canada Logo
08:40 - 07:00
ORD
-
SIN
33h 20m
2 stops
S$ 1,044Air Canada
Sun, 18 Oct - Sun, 25 Oct
Air Canada Logo
07:00 - 20:12
SIN
-
ORD
26h 12m
2 stops
Air Canada Logo
08:40 - 07:00
ORD
-
SIN
33h 20m
2 stops
S$ 1,047Air Canada
Thu, 9 Jul - Sun, 12 Jul
ANA Logo
22:00 - 15:25
SIN
-
ORD
30h 25m
1 stop
ANA Logo
17:45 - 17:15
ORD
-
SIN
34h 30m
1 stop
S$ 1,059ANA
Thu, 9 Jul - Sun, 12 Jul
ANA Logo
06:15 - 20:40
SIN
-
ORD
27h 25m
2 stops
ANA Logo
17:45 - 17:15
ORD
-
SIN
34h 30m
1 stop
S$ 1,068ANA
Wed, 8 Jul - Sat, 11 Jul
Air Canada Logo
06:15 - 20:05
SIN
-
ORD
26h 50m
2 stops
Air Canada Logo
15:40 - 05:15
ORD
-
SIN
48h 35m
2 stops
S$ 1,069Air Canada
Thu, 9 Jul - Sun, 12 Jul
ANA Logo
22:00 - 15:25
SIN
-
ORD
30h 25m
1 stop
ANA Logo
17:45 - 17:15
ORD
-
SIN
34h 30m
1 stop
S$ 1,077ANA
Thu, 27 Aug - Sun, 30 Aug
Delta Logo
07:30 - 22:36
SIN
-
MDW
28h 06m
2 stops
Delta Logo
06:05 - 05:00
MDW
-
SIN
33h 55m
2 stops
S$ 1,483Delta
Thu, 27 Aug - Tue, 6 Oct
Delta Logo
07:30 - 22:36
SIN
-
MDW
28h 06m
2 stops
Delta Logo
09:29 - 23:55
MDW
-
SIN
25h 26m
2 stops
S$ 1,487Delta
Thu, 9 Jul - Sun, 12 Jul
Multiple Airlines Logo
15:20 - 05:00
SIN
-
MDW
26h 40m
2 stops
Multiple Airlines Logo
21:35 - 11:55
MDW
-
SIN
25h 20m
2 stops
S$ 1,672Multiple Airlines
Wed, 8 Jul - Sat, 11 Jul
Multiple Airlines Logo
15:20 - 05:00
SIN
-
MDW
26h 40m
2 stops
Multiple Airlines Logo
21:00 - 11:55
MDW
-
SIN
25h 55m
2 stops
S$ 1,680Multiple Airlines
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 round-trip 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$ 859 on average for return flights. On the other hand, the most expensive months are April and May, where the average cost of tickets from Singapore is S$ 1,221 and S$ 1,214 respectively. For one-way flights, the best month to travel is July with an average price of S$ 553.

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$ 295.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonFebruary
Cheapest flightS$ 613
Best time to beat the crowds (38% less expensive on average)
Most popular time to fly (73% 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 1482 reviews
8.7Crew
8.1Food
8.4Boarding
8.3Comfort
8.0Entertainment
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

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

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.

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.

Food was excellent, the crew was exceptionally friendly, and the seats were comfortable. Bathroom were also kept very clean and odor free.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

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.