Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

Find cheap flights to Chicago from S$ 843

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 24-5. 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
Fri 24-5
Fri 31-5

Search 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
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
In the last 7 days, travellers have searched 45,119,101 times on KAYAK, and here's why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheap flight deals to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 and deals for you by selecting your travel dates.
Choose your dates
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,322EVA Air
Find Deal
Mon, 23 Sep - Thu, 26 Sep
08:35 - 07:25SIN-ORD
35h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,330Air India
Find Deal
Mon, 23 Sep - Fri, 27 Sep
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,356EVA Air
Find Deal
Sat, 21 Sep - Fri, 27 Sep
08:05 - 23:56SIN-ORD
28h 51m2 stops
13:20 - 00:20ORD-SIN
46h 00m2 stops
S$ 1,471Japan Airlines
Find Deal
Mon, 23 Sep - Fri, 27 Sep
22:30 - 09:30SIN-ORD
24h 00m1 stop
12:20 - 05:00ORD-SIN
27h 40m1 stop
S$ 1,490Korean Air
Find Deal
Mon, 7 Oct - Thu, 24 Oct
01:50 - 00:16SIN-ORD
35h 26m2 stops
12:25 - 06:15ORD-SIN
28h 50m1 stop
S$ 1,507Japan Airlines
Find Deal
Fri, 21 Jun - Tue, 9 Jul
08:45 - 22:53SIN-ORD
27h 08m2 stops
05:00 - 20:15ORD-SIN
25h 15m2 stops
S$ 1,601United Airlines
Find Deal
Tue, 15 Oct - Thu, 7 Nov
21:00 - 04:54SIN-ORD
20h 54m1 stop
21:10 - 18:45ORD-SIN
32h 35m2 stops
S$ 1,644United Airlines
Find Deal
Mon, 23 Sep - Fri, 27 Sep
01:10 - 09:30SIN-ORD
21h 20m1 stop
12:20 - 05:00ORD-SIN
27h 40m1 stop
S$ 1,789Korean Air
Find Deal
Sun, 6 Oct - Sat, 26 Oct
06:15 - 14:55SIN-ORD
21h 40m1 stop
07:10 - 00:45ORD-SIN
28h 35m2 stops
S$ 1,987ANA
Find Deal
Wed, 9 Oct - Tue, 22 Oct

Flights to Chicago - Travel Insights & Trends

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 day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Monday where tickets can be as cheap as S$ 1,669. On the other hand, the most expensive day to fly is Thursday, where prices are S$ 2,502 on average.

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 October, where tickets cost S$ 1,490 on average for one-way flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Singapore is S$ 2,371 and S$ 2,319 respectively. For return trips, the best month to travel is October with an average price of S$ 1,490.

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

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost S$ 1,733 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is S$ 1,933.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 44 days before departure.

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 O'Hare Intl Airport, with an average flight price of S$ 513.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 86% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Singapore, which takes 20h 35m.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 843
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 6% lower 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.

  • Which airline offers the most flights to Chicago?

    Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,848 per week, followed by American Airlines with 3,726 flights per week.

See more FAQs

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?

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, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

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
ANAOverall score based on 948 reviews
8.8crew
7.8food
8.0entertainment
8.3comfort
8.6boarding
Airline reviews

Staff and crew are wonderful, professional and courteous. Meal is delicious and snacks can be improved. Entertainment needs improvement, pls update selections of movies. I appreciate that our flight was on time

8.0 ExcellentTheresa, Apr 2024NRT - HNL
Read more about ANA reviews

Staff and crew are wonderful, professional and courteous. Meal is delicious and snacks can be improved. Entertainment needs improvement, pls update selections of movies. I appreciate that our flight was on time

I flew economy class so of course it’s not as roomy as business and first class. But overall it was ok and the seat had an interesting way to recline — the seat itself extended forward instead of the backrest. This way the person sitting behind me would not lose space by my reclining—excellent concept. I wish all airlines used these seats.

Flying with ANA is always a breeze. Seats are very comfortable.

For the price of a seat that is obviously crammed together so as to get many more people onboard and combined with the long flight duration, Free WiFi should be an automatic “Thank You for Flying with Us!” To charge an additional fee when so many other businesses offers it is a bit “cheap” on the airline’s part.

Food was high quality. Crew was extremely professional, polite, attentive. Flights were on time. Plane had good media tech.

I wish the serve should leach and drink. Maybe because only 2hr

It was ok I thought because my flight was 1pm i was expecting to have lunch but it didn’t and after 7 hr finally dinner time was only chicken sandwich and next breakfast was an hour before plane land in Tokyo. so I should bring some food with me. Japanese flight attend was nice but the other was chewing gum and how she ask and respond to customers was not professional I felt. Maybe because Japan flight attendant is highly train and everyone looked very dress and professional so I was kind disappointed. I like that the bathroom was very clean .

Lovely airport at Haneda. Great food selection. Spacious and private boarding area with dedicated bathroom for each gate.

They did not get my request for veg food that i made a month ago. Also did not have any backup veg food on board or fruit plate or simething. Very disappointing as i had hward about how grwat ANA was supossed to be. Alsio entertainment was lacking and screen and tech was subpar. Overall just mid to low tie. They are living off reputation and are being passed up by most other carriers.

Ana is absolute world class They should not work with united

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

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.

The crew is so cold and indifferent but I have to appreciate their professionalism. The seat is too hard and not comfortable at all. Entertainment is very limited and not of many choices.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

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.

t and I Flight crew did excellent job taking care of us and feeding us and staying professional. The boarding was delayed by an hour and then extra security measures were taken. No real explanation except for they said it was more of a maintenance dey

At least it was not very cold inside the plane. I noticed there was now a bidet in the bathroom and that’s good! I didn’t like the window seat. Flight was smooth except for 1 turbulence. Plane was on time. Thanks. Food was not that great. Miso and green tea were good! As usual movies were old and there were no changes.

Food as always. PA was not clear, especially the English ones. Very limited Hollywood movies. Unlike the first flight I had, this plane has less leg room and less room for my under seat baggage.

Great crew, Japanese domestic flight is just a drink service but crew are very attentive

I didn’t like the check in process I had to check in at the counter took too much time . Didn’t give the upgrade my seat .

Japan airlines is excellent. I had a great flight with them, and they are the consummate professionals. I booked my flight through Kayak and they sent it on to Underpricer. That felt really scammy. My Oneworld number would not attach to the reservation and I could not choose a seat. I called Japan Airlines and got one but it was in the back. Later I drove to the airport and worked with the excellent agents there to find a better one. Later that day, I got a phone call from Underpricer trying to upsell me the option of choosing a seat. It felt like a Spirit Airlines level crappy move. The flight itself was exactly as nice as you would expect from JAL. The meal was good and the flight crew was awesome.

Need new movies, a lots of them are 20-10 years old or older. It us a very long flight we need good entertainment. Please load more new movies!

Good and movies are so old. Needs to have more up-to-date movies.

It was one of the best experiences. The staff were amazing. JAL is my second favorite Asian Carrier I have flown on. Korean Air was my first. Thank you JAL for bringing me home safely and for such an amazing staff and service.

JAL is quite nice in business class. Comfortable, spacious seats. Their entertainment, especially their film selection, isn’t that great though as their are not many new releases like some airlines offer their first and business class customers. . Food is excellent and the option to order on demand is always quite nice, which JAL offers. Flight attendants were very friendly and kind. Overall very good experience with JAL.

Very comfortable unlike my first trip where they switched my flight from JAL to AA which was a disaster!

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Air India lounge in Delhi , was very disappointing! The food was of poor quality and options were limited especially for vegetarians!! Beverages were fine. The in flight crew was excellent! . They helped me with my seat controls - the controls did not work without a hassle or assistance!! A very poor showing for a Business cabin!!! Post flight , the wheel chair passengers ( including Me) were “ shepherded and left waiting twice (an hour or more) before taking us to immigration! I chose to Fly Air India because I want. to patronize our National carrier with the hope that the experience will improve!!! Regrettably, I will have to look at other options for my next trip to India

Entertainment system was not working and was told I would get a voucher and have not got one. No toiletries were available not even a toothbrush false sweet talk by ground staff

Worst International flight I ever had in my whole life time. Boarding is the worst of all and flight experience was also not good. Screens were not working, seats were not comfortable and lot more.

Very very impressed with the proactive care and alertness with which ABHISHEK Chowdhary took care of us. Quietl,dignified , very alert, and meticulous. Very impressed. Also with SUNiL Kumar who was there for us in a very helpful way. SHERLY ALEX On Flight 119, BOM TO JFK CUSTOMER ON SEAT 21C, 21ST March 2024

If you are traveling to mumbai -- must try SFO - MUM direct flight. It's a game changer when you are traveling to India. Timings are well designed, optimal and makes the travel enjoyable.

Air India needs to launch new planes. Seats are worn out, most of the plane's TV screens wasn't working, USB charging ports wasn't working as well so I can charge my phone & watch my download movies, Food was mediocre, the plane smells. How can Air India put through their customers with this bad experience? This complaint needs to get escalated to the upper management. How shameful is the upper management to improve this plane? The flight is going back & forth from NEW YORK & DELHI. Two of the big cities in the world and this is how your experience is for sitting in a plane for 12+ hrs? Get your planes fixed ASAP Air India (TATA Management do your job right).

One of my worst experiences. Nothing was working in the flight. Entertainment system was broken, seat was very uncomfortable, crew did not offer water until food was provided, lights were not working, attendant call was not working. In short everything was broken and duct taped.

Old aircraft, crew were so so. Meals were mediocre. Flight to delhi was delayed. Lounge needs update and was mediocre too.

Bathrooms were horrible and no cleaning. Announced baggage claim carousel as one but came to a different one. People were waiting

Every thing was so old…. Can’t believe they are able to charge so much for this terrible level of service will use alternate company in future for all travel needs

Book Cheap Chicago Plane Tickets

Recent return flight deals

 
These are the cheapest return flights to Chicago found on KAYAK in the last 72 hours.
23-9Mon
1 stopEVA Air
20h 35mSIN-ORD
26-9Thu
1 stopEVA Air
24h 20mORD-SIN
S$ 1,322
23-9Mon
1 stopAir India
35h 50mSIN-ORD
27-9Fri
1 stopAir India
30h 30mORD-SIN
S$ 1,330
21-9Sat
1 stopEVA Air
20h 35mSIN-ORD
27-9Fri
1 stopEVA Air
22h 30mORD-SIN
S$ 1,356
23-9Mon
2 stopsJapan Airlines
28h 51mSIN-ORD
27-9Fri
2 stopsJapan Airlines
46h 00mORD-SIN
S$ 1,471
7-10Mon
1 stopKorean Air
24h 00mSIN-ORD
24-10Thu
1 stopKorean Air
27h 40mORD-SIN
S$ 1,490
21-6Fri
2 stopsJapan Airlines
35h 26mSIN-ORD
9-7Tue
1 stopJapan Airlines
28h 50mORD-SIN
S$ 1,507
15-10Tue
2 stopsUnited Airlines
27h 08mSIN-ORD
7-11Thu
2 stopsUnited Airlines
25h 15mORD-SIN
S$ 1,601
23-9Mon
1 stopUnited Airlines
20h 54mSIN-ORD
27-9Fri
2 stopsUnited Airlines
32h 35mORD-SIN
S$ 1,644
6-10Sun
1 stopKorean Air
21h 20mSIN-ORD
26-10Sat
1 stopKorean Air
27h 40mORD-SIN
S$ 1,789
9-10Wed
1 stopANA
21h 40mSIN-ORD
22-10Tue
2 stopsANA
28h 35mORD-SIN
S$ 1,987

Search by stops

Search by airline

Search by price

Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
24-5Fri
3 stops
45h 55mSIN-ORD
S$ 843
18-6Tue
3 stops
36h 32mSIN-ORD
S$ 886
17-6Mon
3 stops
37h 21mSIN-ORD
S$ 919
21-6Fri
1 stopEVA Air
20h 50mSIN-ORD
S$ 1,038
19-6Wed
1 stopAir India
35h 50mSIN-ORD
S$ 1,164
17-6Mon
1 stopAir India
35h 50mSIN-ORD
S$ 1,194
18-5Sat
2 stopsJapan Airlines
30h 48mSIN-ORD
S$ 1,275
23-7Tue
2 stopsJapan Airlines
35h 28mSIN-ORD
S$ 1,405
23-5Thu
2 stopsKorean Air
24h 30mSIN-MDW
S$ 1,935
7-8Wed
2 stopsKorean Air
27h 01mSIN-MDW
S$ 2,575

Search by stops

Search by airline

Search by price

Recent domestic flight deals

14-5Tue
directSpirit Airlines
2h 37mLGA-ORD
15-5Wed
directSpirit Airlines
2h 09mORD-LGA
S$ 135
14-5Tue
directSpirit Airlines
2h 39mLGA-ORD
15-5Wed
multi-stopSpirit Airlines
12h 22mORD-LGA
S$ 150
9-7Tue
directJetBlue
2h 46mJFK-ORD
10-7Wed
directJetBlue
2h 23mORD-JFK
S$ 173
29-5Wed
directJetBlue
2h 54mBOS-ORD
29-5Wed
directJetBlue
2h 26mORD-BOS
S$ 173
9-7Tue
directDelta
2h 34mLGA-ORD
9-7Tue
directDelta
2h 19mORD-LGA
S$ 173
14-8Wed
directDelta
2h 33mLGA-ORD
14-8Wed
directDelta
2h 12mORD-LGA
S$ 174
21-5Tue
directUnited Airlines
2h 40mLGA-ORD
22-5Wed
multi-stopUnited Airlines
6h 22mORD-LGA
S$ 290
29-5Wed
directUnited Airlines
2h 35mEWR-ORD
30-5Thu
directUnited Airlines
2h 23mORD-EWR
S$ 298
4-5Sat
directAmerican Airlines
3h 58mLAX-ORD
9-5Thu
directAmerican Airlines
4h 27mORD-LAX
S$ 842
19-5Sun
multi-stopAmerican Airlines
6h 40mLAX-ORD
22-5Wed
directAmerican Airlines
4h 27mORD-LAX
S$ 995

Search by stops

Search by airline

Search by price

Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
25-4Thu
multi-stopJapan Airlines
34h 30mSIN-ORD
4-5Sat
multi-stopJapan Airlines
46h 35mORD-SIN
S$ 1,532
25-4Thu
multi-stopAmerican Airlines
40h 59mSIN-ORD
4-5Sat
multi-stopAmerican Airlines
28h 50mORD-SIN
S$ 1,644
25-4Thu
multi-stopANA
21h 40mSIN-ORD
4-5Sat
multi-stopANA
23h 55mORD-SIN
S$ 1,837
25-4Thu
multi-stopEVA Air
20h 50mSIN-ORD
3-5Fri
multi-stopEVA Air
24h 20mORD-SIN
S$ 2,132
25-4Thu
multi-stop
29h 55mSIN-ORD
4-5Sat
multi-stop
31h 50mORD-SIN
S$ 2,258
25-4Thu
multi-stop
28h 13mSIN-ORD
4-5Sat
multi-stop
27h 03mORD-SIN
S$ 2,638
25-4Thu
multi-stop
29h 23mSIN-ORD
3-5Fri
multi-stop
24h 20mORD-SIN
S$ 2,661
25-4Thu
multi-stopEVA Air
20h 50mSIN-ORD
3-5Fri
multi-stopEVA Air
22h 30mORD-SIN
S$ 2,728
25-4Thu
multi-stopEVA Air
20h 50mSIN-ORD
4-5Sat
multi-stopEVA Air
27h 03mORD-SIN
S$ 2,747
25-4Thu
multi-stopCathay Pacific
31h 15mSIN-ORD
4-5Sat
multi-stopCathay Pacific
24h 25mORD-SIN
S$ 3,161

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - Singapore

Cabin classes: