S$ 670 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 5-2. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest return fare
S$ 1,189
Typical prices: S$ 1,158-S$ 1,298
Multiple Airlines
Wed 25-2Thu 5-3
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 654
Typical prices: S$ 799-S$ 846
IndiGo
Thu 5-2
SIN - ORD • 2 stops
When to travel
September
Cheapest • 20% price drop
June
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

Wed, 25 Feb - Thu, 5 Mar
Multiple Airlines Logo
02:20 - 07:35
SIN
-
ORD
19h 15m
1 stop
Multiple Airlines Logo
15:54 - 09:35
ORD
-
SIN
27h 41m
2 stops
S$ 1,189Multiple Airlines
Tue, 17 Feb - Wed, 18 Feb
United Airlines Logo
22:20 - 05:12
SIN
-
ORD
20h 52m
1 stop
United Airlines Logo
09:01 - 08:00
ORD
-
SIN
32h 59m
1 stop
S$ 1,196United Airlines
Mon, 23 Feb - Mon, 2 Mar
United Airlines Logo
10:10 - 21:36
SIN
-
ORD
25h 26m
1 stop
United Airlines Logo
14:35 - 08:00
ORD
-
SIN
27h 25m
1 stop
S$ 1,202United Airlines
Tue, 10 Feb - Fri, 20 Feb
United Airlines Logo
22:20 - 06:25
SIN
-
ORD
22h 05m
1 stop
United Airlines Logo
06:25 - 20:15
ORD
-
SIN
23h 50m
1 stop
S$ 1,204United Airlines
Wed, 11 Feb - Sat, 14 Feb
United Airlines Logo
22:20 - 06:20
SIN
-
ORD
22h 00m
1 stop
United Airlines Logo
16:20 - 20:15
ORD
-
SIN
37h 55m
1 stop
S$ 1,206United Airlines
Mon, 23 Feb - Mon, 2 Mar
Japan Airlines Logo
08:15 - 21:35
SIN
-
ORD
27h 20m
2 stops
Japan Airlines Logo
07:00 - 00:50
ORD
-
SIN
27h 50m
2 stops
S$ 1,218Japan Airlines
Wed, 4 Mar - Tue, 17 Mar
Delta Logo
22:30 - 23:56
SIN
-
ORD
39h 26m
2 stops
Delta Logo
09:50 - 00:10
ORD
-
SIN
25h 20m
2 stops
S$ 1,224Delta
Thu, 12 Mar - Thu, 19 Mar
Multiple Airlines Logo
13:15 - 20:35
SIN
-
ORD
20h 20m
1 stop
Multiple Airlines Logo
12:05 - 19:10
ORD
-
SIN
42h 05m
2 stops
S$ 1,253Multiple Airlines
Mon, 23 Feb - Mon, 2 Mar
Japan Airlines Logo
08:15 - 07:35
SIN
-
ORD
37h 20m
1 stop
Japan Airlines Logo
06:00 - 00:50
ORD
-
SIN
28h 50m
2 stops
S$ 1,254Japan Airlines
Thu, 26 Feb - Thu, 5 Mar
Delta Logo
10:40 - 09:06
SIN
-
MDW
36h 26m
2 stops
Delta Logo
06:00 - 05:00
MDW
-
SIN
33h 00m
2 stops
S$ 1,557Delta
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 September, where tickets cost S$ 1,072 on average for one-way flights. On the other hand, the most expensive months are January and June, where the average cost of tickets from Singapore is S$ 1,572 and S$ 1,513 respectively. For return trips, the best month to travel is September with an average price of S$ 1,072.

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, with an average flight price of S$ 270.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightS$ 654
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly (12% 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 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 1334 reviews
8.3Comfort
8.4Boarding
8.6Crew
8.0Entertainment
8.1Food
Airline reviews

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.

8.0 ExcellentJolene, Jan 2026
TPE - DFW
Read more EVA Air reviews

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 love EVA airline, but the KAYAK website for not in emergency, urgency and personal issues. For instance, on January 5/2026 with already booked the flight, I have a 15 hours of delay between airport when booked before as my choice. But if I want to go back home (U.S) early, then I have to contact the KAYAK office at I was in other country without phone service and nothing that EVA can do for me. Even I offered to pay more to change from another flight to go to the U.S early, not wasting at15 hours of delay, but EVA could not help me until I call KAYAK at an Island of nation. No office of KAYAK from any nation and times of difference in the world. However, everything and everyone is the best. Therefore, please KAYAK making much more easy for both the airline and passenger in some issues at the middle of nowhere in some country when no need to call KAYAK for some emergency, urgency, sick, etc or personal reference. Please, please, please no need to call KAYAK office for any changes of flights from urgency or private.

My seat arrangement was good with Eva Air. The toilet sanitary was good ( hand wash, face moist spraying, fresh air spray, hair moisturizer). But the Asian movie selection was not great at all.

Overall is good. But Asian movie selection was not great at all. And also more snack food to give out

Don’t preorder the diabetic meal if you don’t have to. Whoever creates those meals thinks everyone loves fish, and hates seasoning. In a world where we can find diabetic friendly candy and low card bread, it’s surprising that places are still serving flavorless gelatin and rice cakes. Boarding in Taipei was chaos. They tried to form a line but didn’t manage it. So once the gate was opened, the line didn’t matter and everyone just mobbed to the front.

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

Its fantastic!!I like the food the serve in EVA air😊

It was very long way flight but its good I like the food they serve in EVA air its really good!

Flight was canceled was only given only a 8 hour lead time. Had to fight to be put on another airline (United Airlines) that was leaving earlier then the one EVA and rescheduled.

The plane was very clean and the crew was very nice.

The lounge in Japan was busy and smaller. Have great choice of ramen.

Customer service was very good. Food was delicious. Wish the flight was longer.

I was good seat to keep stretch my legs . but couldn’t keep my bag in my hand . because they told me can’t keep my seat is no holder , because no seat fronts of us. wish I can put my leg on something higher. but instead of that everything goood.

Overall was a good experience. Crew members are nice and helpful.

Good airlines btu ORL airport messed up the return flight for me. Checking out a connecting flight pax is unacceptable.

The pilot was kept warning about the weather terrifying us. The flight attendants were not warm or pleasant.

I couldn’t sit with my daughter. we are separate and both seat was not window or halway side. in the middle. if we sit together will be share comfort seat and more easy travel. this is bad.

Although the flight was delayed because of the equipment came in late, I still give them excellent service ..good food selection and in flight entertainment were sufficient.. I will continue to fly with them

Staff was rude and loud. No respect for customers unlike the Starflyer Osaka to Haneda sector where service was outstanding. What a stark difference. Maybe United should learn from ANA how to do customer service.

Flight delayed first from bad weather, then after boarding there was a problem with the plane. We had to get off and onto another plane...connections were missed and the trip took an additional 10 hours!! Pre-paid seatting was not honored due ro last minute carrier changes. Most of the trip was on Japan Airline.

Vegetarian options should be included with every meal. Even just simple steamed vegetables and whole grains would capture a wide audience.

Cramped, hot and the plane was grubby. Also the plane was an hour late and it took an hour to get my luggage once I got to LAX.

Extensive delays, poor organization to board people, as it felt like chaos to get inside of the plane. No lines, everyone gathering together like a mayhem, very confusing. Passengers out of hand and rude, which is not the airlines fault. However, there should be rules, e.g., not letting one passenger take 2+ spots in the overhead bin.

The bed was alright in business class. Food variety and quality were not up to the mark compared to the business class airfare.

Food , drink experience were great with Cathay. Crew service was excellent. Clean toilet and full snack bars always, pilot took of 26minutes later when boarding at Hong Kong with extra US customs check at gate 9 for US flight, but he managed to arrive only 2 minutes later from flight tracker. Smooth flight .

I wish there were more bathrooms available on these larger carriers.

The experience was efficient, on time, and provided great service.

one hour transit not good. cathay pacific is not helpful at all

My flight was suppose to be at 7:45pm to fly but it didnt fly out until 8:55 to dallas so then all of my other flights was late and delay ihad to wait at the airport for extra 14 hours to be able to get on a different plane

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

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.