S$ 648 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 25-2. 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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Everything you should know

Cheapest return fare
S$ 1,180
Typical prices: S$ 1,234-S$ 1,256
IndiGo
Wed 11-2Wed 18-2
SIN - ORD • 2 stops
Cheapest one-way flight
S$ 648
Typical prices: S$ 813-S$ 860
Multiple Airlines
Wed 25-2
SIN - ORD • 2 stops
When to travel
September
Cheapest • 22% 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, 11 Feb - Wed, 18 Feb
IndiGo Logo
19:40 - 18:25
SIN
-
ORD
36h 45m
2 stops
IndiGo Logo
20:20 - 10:15
ORD
-
SIN
47h 55m
2 stops
S$ 1,180IndiGo
Mon, 2 Feb - Mon, 16 Feb
Multiple Airlines Logo
11:15 - 18:25
SIN
-
ORD
45h 10m
2 stops
Multiple Airlines Logo
13:30 - 18:55
ORD
-
SIN
39h 25m
1 stop
S$ 1,187Multiple Airlines
Tue, 17 Feb - Wed, 18 Feb
United Airlines Logo
22:20 - 06:19
SIN
-
ORD
21h 59m
1 stop
United Airlines Logo
09:01 - 08:00
ORD
-
SIN
32h 59m
1 stop
S$ 1,202United Airlines
Tue, 30 Jun - Wed, 15 Jul
United Airlines Logo
08:45 - 00:58
SIN
-
ORD
29h 13m
1 stop
United Airlines Logo
15:35 - 06:15
ORD
-
SIN
25h 40m
1 stop
S$ 1,208United Airlines
Sun, 28 Jun - Sat, 8 Aug
United Airlines Logo
20:40 - 05:57
SIN
-
ORD
22h 17m
1 stop
United Airlines Logo
21:39 - 18:35
ORD
-
SIN
31h 56m
1 stop
S$ 1,209United Airlines
Sun, 15 Mar - Thu, 19 Mar
Multiple Airlines Logo
21:15 - 08:35
SIN
-
ORD
48h 20m
2 stops
Multiple Airlines Logo
14:10 - 06:40
ORD
-
SIN
27h 30m
2 stops
S$ 1,216Multiple Airlines
Sat, 28 Feb - Sat, 7 Mar
Delta Logo
22:30 - 22:31
SIN
-
MDW
38h 01m
2 stops
Delta Logo
16:13 - 00:10
MDW
-
SIN
41h 57m
2 stops
S$ 1,239Delta
Sat, 28 Feb - Sun, 8 Mar
Korean Air Logo
01:35 - 22:31
SIN
-
MDW
34h 56m
2 stops
Korean Air Logo
09:35 - 00:10
MDW
-
SIN
25h 35m
2 stops
S$ 1,252Korean Air
Sun, 1 Mar - Sun, 8 Mar
Korean Air Logo
22:30 - 21:30
SIN
-
ORD
37h 00m
2 stops
Korean Air Logo
09:50 - 00:10
ORD
-
SIN
25h 20m
2 stops
S$ 1,252Korean Air
Sun, 1 Mar - Sun, 8 Mar
Turkish Airlines Logo
10:15 - 10:05
SIN
-
ORD
37h 50m
1 stop
Turkish Airlines Logo
21:20 - 08:35
ORD
-
SIN
22h 15m
1 stop
S$ 1,266Turkish 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 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$ 1,091 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$ 2,036 and S$ 1,539 respectively. For return trips, the best month to travel is September with an average price of S$ 1,091.

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$ 275.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightS$ 648
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly (9% 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 1324 reviews
8.6Crew
8.1Food
8.4Boarding
8.0Entertainment
8.3Comfort
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
TPE - SFO
Read more EVA Air reviews

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

Flight attendants were very helpful and nice. Would be nice to board on time.

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.

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😊

My ticket was with EVA Airlines, but Asiana Airlines was the ground crew for EVA Airlines. Me and my family member finally received our boarding passes after waiting to check-in, which took over 30 minutes. I had never done a tax refund before, so I crossed immigration without going to customs to receive a stamp for my tax refund. When I went to the tax kiosk on the other side of the immigration gate, NICE Tax Refund asked me to talk to an airline staff member. I could not find any airline staff member, so I went to the Information Desk. The woman at the Information Desk told me and showed me a sign that read that I needed an airline staff member to accompany me to cross immigration again. The woman at the Information Desk phoned EVA Airlines and Asiana Airlines. I also phoned, but there was no answer. There was still 80 minutes before my flight would leave. I waited for 45 minutes. I spoke to Information, not one time, but two times and the woman assured me that this situation happens often and it is nothing to worry about as the airport is small and once the airline staff arrives, it would only take 10 minutes to go get the stamp and I would be able to make my flight. Then, 35 minutes before my flight was scheduled to leave an Asiana Airline employee, accompanied by the woman from the Information Desk came. Asiana asked me to confirm whether I wanted the customs declaration stamp. I answered yes. Then, she said she would like to state that I should take full responsibility if I could not make my flight. She asked whether I wanted her to proceed to contact a staff member to take me to get the stamp. This was very suspicious as there was still 35 minutes remaining until the flight took off. I directly said to her that the question was very strange, but as there was enough time remaining, I did not see a problem and wanted a staff member to accompany me to get the stamp. She went away and came back 5 minutes later and asked me whether I had the item I wanted to declare on me and how many people were traveling with me. I told her I had the item with me and I was here with a family member. She then went away again for another 5 minutes. When she came back she asked whether all members would not be traveling as well. I stated that I am not sure why me or my family member should not board the airplane. At this point, it became apparent that she was not helpful, so I tried to talk to other airline staff. I also talked to a woman wearing a reflective safety vest, who was organizing the gate bollards for boarding and she said she would take me after boarding. When I asked, how I would board the plane, she then said, you will not be able to. I then talked to a man, who spoke Mandarin and appeared to work for EVA Airlines. He told me it was my fault and not his and tried to re-direct me to another person. He was not busy at all. At this point, it became apparent that, Asiana Airlines and EVA Airlines, were more interested in delaying and preventing me from boarding the airplane. In the time the airline staff wasted arguing with me, they could have just brought me to receive the stamp. It seemed apparent that I was not going to receive the stamp or the tax refund, so I stepped into the boarding queue line. Again, the airline staff, the woman in the reflective safety vest asked me to confirm that I would not be getting on the airplane. I was already boarding! There was written signage of the procedure at your airport’s Information Desk. Then, I was passed to multiple airline staff that were not willing to assist accordingly. There was no one at the customs declaration counter and no one else from the airport to assist me. EVA and Asiana Airlines both avoided responsibility and delayed the procedure. They were rude and indirect about the situation with every attempt to prevent me from boarding. Deterring foreigners to depart from a foreign country over tax refund issues is unlawful.

The crew very accommodating and food too is good. Keep up the good work

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 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.

The meals were sufficient and tasty considering it was air travel food. Water coffee and juices offered each time a meal came by and water distributed between meals. It was good service in my opinion. Plenty of movies to enjoy. May not be the one you want but plenty of older movies and plenty of current ones as well. I enjoyed the trip.

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.

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

The flight was just ok, but the vendor made it exceptio ally bard to manage my own reservation and would not give me access. The blocked all of the one time pins to come to their email address which caused me.to go through them eceryrime to get seats see rhe reservation and even get wheelchair access for my sick 71 year old uncle. They only xommunicates via a bot which gave me incorrect info. I thought this was Kayak and not underprivileged. They ruined his trip, did not get him aisle seats and made it impossible to purchase extra leg room. It was a horrible experience. He was taken to hospital on arrival only to find he had blood clots and pnemonia while trying to navigate the airport. This vendor is very irresponsible and the airline could not access his info.

Super delayed. Unnecessary. Need more competent people doing logistics to keep things moving on time. Totally unacceptable.

Overall, not good. Super late boarding in Hong Kong because some last minute issue with a plane. The boarding process is chaotic. Kathy Pacific should seek to do better with punctual departure time. Caused a lot of trouble with missed connecting flight.

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??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

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.