S$ 618 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$ 1,128
Overall average: S$ 1,250
Korean Air
Fri 13-2Fri 20-2
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 618
Multiple Airlines
Wed 25-2
SIN - MDW • 3 stops
When to travel
April
Cheapest • 16% 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

Fri, 13 Feb - Fri, 20 Feb
Korean Air Logo
10:40 - 08:40
SIN
-
ORD
36h 00m1 stop
Korean Air Logo
11:25 - 05:00
ORD
-
SIN
27h 35m1 stop
S$ 1,128Korean Air
Mon, 9 Feb - Fri, 20 Feb
Korean Air Logo
01:35 - 08:40
SIN
-
ORD
21h 05m1 stop
Korean Air Logo
11:25 - 05:00
ORD
-
SIN
27h 35m1 stop
S$ 1,129Korean Air
Wed, 4 Feb - Wed, 18 Feb
Korean Air Logo
01:35 - 08:40
SIN
-
ORD
21h 05m1 stop
Korean Air Logo
11:25 - 05:00
ORD
-
SIN
27h 35m1 stop
S$ 1,130Korean Air
Wed, 4 Feb - Wed, 18 Feb
Delta Logo
01:35 - 23:55
SIN
-
ORD
36h 20m2 stops
Delta Logo
06:15 - 00:10
ORD
-
SIN
27h 55m2 stops
S$ 1,132Delta
Tue, 27 Jan - Tue, 3 Feb
IndiGo Logo
11:15 - 18:25
SIN
-
ORD
45h 10m2 stops
IndiGo Logo
20:20 - 10:15
ORD
-
SIN
47h 55m2 stops
S$ 1,164IndiGo
Mon, 16 Feb - Wed, 18 Feb
Korean Air Logo
01:35 - 21:30
SIN
-
ORD
33h 55m2 stops
Korean Air Logo
11:25 - 00:10
ORD
-
SIN
22h 45m1 stop
S$ 1,178Korean Air
Thu, 22 Jan - Wed, 4 Feb
Air Canada Logo
08:50 - 14:41
SIN
-
ORD
19h 51m1 stop
Air Canada Logo
15:35 - 14:50
ORD
-
SIN
33h 15m2 stops
S$ 1,184Air Canada
Thu, 29 Jan - Thu, 5 Feb
IndiGo Logo
19:40 - 18:25
SIN
-
ORD
36h 45m2 stops
IndiGo Logo
20:20 - 17:20
ORD
-
SIN
31h 00m2 stops
S$ 1,195IndiGo
Tue, 17 Feb - Wed, 18 Feb
United Airlines Logo
22:20 - 06:19
SIN
-
ORD
21h 59m1 stop
United Airlines Logo
09:01 - 08:00
ORD
-
SIN
32h 59m1 stop
S$ 1,199United Airlines
Sun, 15 Feb - Sun, 22 Feb
Delta Logo
10:40 - 22:31
SIN
-
MDW
25h 51m2 stops
Delta Logo
18:40 - 00:10
MDW
-
SIN
39h 30m2 stops
S$ 1,412Delta
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 April, where tickets cost S$ 1,210 on average for one-way flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from Singapore is S$ 2,269 and S$ 1,606 respectively. For return trips, the best month to travel is April with an average price of S$ 1,210.

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$ 274.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flightS$ 618
Best time to beat the crowds but there is an average 56% increase in price.
Most popular time to fly (6% more expensive on average)
Flight from Singapore to Chicago Midway 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.

Prefer to fly direct to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop to Chicago.
Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

Singapore to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Tuesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Wednesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Thursday

ANA, Aer Lingus, Aeromexico, +73 more

ANA, Aer Lingus, +74 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Tuesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Wednesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Thursday

ANA, Aer Lingus, Aeromexico, +73 more

ANA, Aer Lingus, +74 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Reviews of the top 5 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 1306 reviews
8.1Food
8.0Entertainment
8.4Boarding
8.6Crew
8.3Comfort
Airline reviews

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

10.0 ExcellentAlexandra, Nov 2025
TPE - ORD
Read more EVA Air reviews

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.

Awful had to ask for a supervisor to sit with my flight companion even t booked the tickets together weeks before

EVA airlines was excellent: on time or early, safe, courteous crew. Highly recommended.

EVA! What is going on with your food!?!? Pre pandemic I used to go to Taiwan at least twice a year and always flew EVA — the food was consistently tasty for airplane food. Post pandemic, it’s not great at all. Step it up!

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. Oh and the seats were more comfortable, had more ability to lean and the headrest was much better for flight sleeping. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

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.

we were in premium economy, but we both got middle seats and had to sit separately. i could have avoided this by trying to obtain seats sooner, but i tried 3 times and gave up. ANA's technology is not friendly for newcomers. no, check that---I think it is nigh impossible. not sure we are coming back. ana can do better to provide a front end that's friendly to users in both US and Japan.

Checking in via an alliance partner, even a foreign one should get TSA Precheck printed on your boarding pass. The paper copy issued by ANA didn’t show it. I couldn’t get my digital copy due to some technical issue arising because I checked in with ANA. The kiosks at SFO similarly threw an error. The only way I could have gotten a new copy of my boarding pass was from the UA counter and lines were nearly as long as TSA so I bit the bullet and went through the regular TSA line. If UA wants my business, they need to improve that process.

Great as can be expected with a 10 hour flight over the Pacific. Great movie selection of new releases that hadn’t hit streaming yet. And despite the bad rep, I actually like the airplane good.

I wouldn’t know, I tried to contact you days before to reschedule my flight back to Okinawa but you left me on hold for 2 hours. I tried calling multiple times and not once did you pick up. I had to spend 2000 dollars on a one way ticket back to Okinawa because I couldn’t get ahold of you guys to change my flight.

I fell asleep, and the crew kindly left some snacks for me

Underpricer is a terrible third party service that couldn’t change three letters on my boarding pass in time to make a flight. It cost me tons of money to have to buy a new ticket with JAL. I’m extremely let down with Kayak using such a sketchy company with horrific customer service.

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

I liked- timely took the take off I disliked- food for ANML was not served even after request, ASVML was really bad, the cleanliness of seats were not up to satisfactory level and I had to use my own sanitizer. Even basic sanitizer packs were not served, cabin crew could be more friendly as I noticed their behavior against other fellow passangers who were not speaking English well.

The crew was attentive and provided everything I needed. The business class food was excellent.

Fantastic flight company. A higher standard than any American airline company for sure.

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

I thought this was a JAL flight but landed up being a code sharing one with Hawaiian Air. Got upgraded by check in staff and they confirmed my bag coming from Bangkok which was great. Cabin crew was solid, not especially friendly, just super efficient and wanting to get the job done which they did. Very fast and agenda oriented. Worst part is my economy plus seat was no better than my economy seat on JAL. Plus JAL has way better food, cleaner plane, and better crew. Worst part is when I landed, was never told where to grab bags. I had correct flight name and number for JAL but there was a Hawaiian flight number in another baggage terminal. I wasted over an hour with no help from ground staff for my bag. Hawaiian and Alaska airlines merger can’t happen fast enough as Hawaiian airlines is a dinosaur. Bad experience again and I’m not surprised. JAL rocks!

The seat was uncomfortable and seemed to be on its last days. Loose and sloppy

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.

Not much of anything could have been done better unless I had a first class ticket. I was literally 15 hours with an airline in the economy class. Very professional friendly and attentive crew. Good airline food, clean cabin, seating area and bathrooms. I've been 4 times back-and-forth with Cathay Pacific, and I would not choose another airline for this trip. Five out of five stars.

Well- trained, cheerful onboard staff. Business class seating and storage were excellent. Outstanding range of food choices, though quality ranged from just OK (seasonal rice and beef dish) to outstanding ( congee and soup noodles with beef brisket). But what can you expect; it's on a plane. I couldn't figure out the remote control, but touch screen worked well. My wife and I (in our 60s), didnt find much to watch from the Entertainment choices. We mostly watched the flight maps. The bedding did the job but is unwieldy and ends up in a clump, with one-third falling on the floor.

First time tying out business class with this airline, hat a disappointment, never returning. We didn’t get the meal as requested from Singapore to HKG flight. While meals served connecting flight, crew takes meal order based off passenger membership status by giving the. Priority selection of meals. It was a battle, plain disappointment, not worth the hype, price, class as categorized/ advertised

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.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

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.