S$ 684 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 18-2. 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.
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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, 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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Cheap Flight Deals 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.

Recent return flight deals to Chicago

Recommended return deals departing in the coming months from the most popular airlines that fly to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
01:25 - 14:00SIN-ORD
25h 35m1 stop
15:40 - 05:40ORD-SIN
25h 00m1 stop
S$ 1,275Cathay Pacific
Find Deal
Mon, 10 Mar - Tue, 18 Mar
20:15 - 13:00SIN-ORD
30h 45m1 stop
15:40 - 05:40ORD-SIN
25h 00m1 stop
S$ 1,280Cathay Pacific
Find Deal
Mon, 3 Mar - Mon, 10 Mar
20:15 - 13:00SIN-ORD
30h 45m1 stop
14:40 - 11:55ORD-SIN
31h 15m1 stop
S$ 1,293Cathay Pacific
Find Deal
Mon, 10 Feb - Tue, 18 Feb
00:50 - 23:13SIN-ORD
36h 23m2 stops
11:00 - 06:15ORD-SIN
29h 15m2 stops
S$ 1,320
Find Deal
Sun, 9 Feb - Tue, 18 Feb
00:50 - 23:13SIN-ORD
36h 23m2 stops
13:10 - 14:15ORD-SIN
35h 05m3 stops
S$ 1,347
Find Deal
Sun, 9 Feb - Tue, 18 Feb
10:45 - 15:05SIN-ORD
42h 20m1 stop
10:35 - 08:00ORD-SIN
31h 25m2 stops
S$ 1,420United Airlines
Find Deal
Wed, 5 Feb - Fri, 7 Feb
15:45 - 20:35SIN-ORD
41h 50m1 stop
00:30 - 14:30ORD-SIN
25h 00m1 stop
S$ 1,441EVA Air
Find Deal
Mon, 10 Mar - Thu, 13 Mar
13:15 - 20:35SIN-ORD
20h 20m1 stop
00:30 - 12:05ORD-SIN
22h 35m1 stop
S$ 1,451EVA Air
Find Deal
Tue, 11 Mar - Mon, 17 Mar
10:10 - 13:09SIN-ORD
40h 59m3 stops
06:30 - 20:15ORD-SIN
23h 45m1 stop
S$ 1,485United Airlines
Find Deal
Wed, 5 Feb - Fri, 7 Feb
02:20 - 17:17SIN-ORD
28h 57m2 stops
08:15 - 00:50ORD-SIN
27h 35m2 stops
S$ 2,105Japan Airlines
Find Deal
Sun, 2 Mar - Mon, 10 Mar

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 round-trip 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 Tuesday where round-trip tickets can be as cheap as S$ 1,613. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,385 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$ 1,436 on average for return flights. On the other hand, the most expensive months are August and June, where the average cost of tickets from Singapore is S$ 2,026 and S$ 1,887 respectively. For one-way flights, the best month to travel is October with an average price of S$ 1,436.

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

The average price for all round-trip 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 round-trip flights cost S$ 1,549 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$ 1,802.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 19 weeks 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 (ORD), with an average flight price of S$ 541.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 684
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly (4% 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.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be July, August and September. The cheapest month to fly from Singapore is October.
  • 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, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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
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
EVA AirOverall score based on 1253 reviews
8.1Food
8.0Entertainment
8.4Boarding
8.3Comfort
8.6Crew
Airline reviews

Great but I am not sure why I was placed in zone 4 for boarding despite being an Infinity Member??? Can you explain online. Thanks

10.0 ExcellentM, Jan 2025TPE - SEA
Read more EVA Air reviews

Great but I am not sure why I was placed in zone 4 for boarding despite being an Infinity Member??? Can you explain online. Thanks

basic and only minimum of service, they offer nothing special

The staff was marvelous. The entertainment options were terrible, old or 2nd rate movies. I was unable to entertain myself for 18 hours-it made it seem even longer. Note: I thought about upgrading but your information about what was included was unclear. Are the seats bigger? Are there current moves? What kind of food do you get? Would the upgrade compare to Delta? Just saying the upgrade is better didn’t convince me and I regret not flying Delta.

Crew's attitude can be better. I asked one crew member to help to put carry on baggage into overhead bin, but he was not willing to help. I needed help because my height is short. His attitude was bad.

Plane is new and I was upgraded to first class so all was great.

Food was ok. Could have been better. Entertainment was limited, especially for kids.

EVA Air flight from Wien to Taipei is good, but the on-ground service to arrival gate is bad.

The flight from Taipei to LAX was the first time we encountered rudeness from the crew. From the gate agents to the in flight crew. We had received such wonderful service going to Bali and on our Bali to Taipei flight that it shocked us when the gate agent was rude and then the rudeness continued on the flight to LAX.

Overall great experience. All four members of my family were seated together without paying extra to reserve seats. Everything was on time. Food was great and healthy. Media entertainment was good. Rock music could be added as a listening choice. No issue with baggages. Flight attendants were friendly and helpful. I would recommend EVA to friends and family.

The crew was very helpful. Food was prepared with great care and tasted wonderful. Movie selection was a bit limited. The bedding on the seat is a little too thin for sleeping.

Wonderfully pleasant experience. Good meal and beverage selections. Professional air staff.

Seat width can be a bit wider. not nice that they charge extra for the window seats.

Seats were comfortable with excellent legroom. Meals were also quite good. The cabin crew were excellent and very helpful. The check-in experience was also very smooth.

I was very happy with my flight on ANA. The crew were excellent and very helpful throughout the flight. The food was also very good. The seats were comfortable and had excellent legroom. The headphone jack position was annoying, but that is a minor nitpick. The movie selection in the IFE was good, but the TV selection was lacking. Adding English subtitles to the Japanese movies and videos would have been very useful.

The ehole fliht went smoothly. No delays. Bur the food was not good.

Wonderful. I love ANA airlines. It's the best so far. My first pick when I travel now.

Just okay. Staff is accomodating especially at the check in counter and gate. Boarding was just fine. Leg room was cramped at economy. No entertainment, wifi is so-so. Cola in can given by cup, but rest of can was not given. At least give the whole can.

What I noticed is that when customers or passengers are asleep, they are no longer given food.

Flight were late each leg of the trip, seats were narrow and uncomfortable. Food was delayed and poor quality. Overall a bad e perience. I complained and was offered no offset or compensation.

I ask the crew to help me get my bag because I can't reached it she ignore me

Website from the 1990s, super frustrating customer support, inflight experience merely OK - more like United than e.g. Emirates

The seats are significantly more comfortable than US airlines and the staff are much friendlier. The food is also much better, as they are particularly accommodating to any dietary restrictions.

Could had been better if they include in their menu some western food.

They 7 seats in one row for Business class while most business class for other airlines are 4 seats in one row. the seat was narrow. the Toilet was so smell, dimming light, no water out of faucet. Terrible.

Difficult to access advanced check-in online. No way to understand why it wouldn’t work. Call center not answering. Email for answers took days to respond, Kind service at the airport and on the flight made up for disappointing service before flight.

Courteous and helpful employees. Comfortable seats and temperature of aircraft . Did not need squid in my salad but glad to have the menu information advising me of what it was

Everything was great, except the Wifi, but that's understandable.

The plane was dirty, there was trash in the seat pocket in front of me.

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

They woke us up 2.5 hours before the flight was over? Why? If I'm on a long haul flight I want to sleep as much as possible. Also, didn't mention the mattress pads in business class so missed out on using those. The western meal of truffle, salmon pasta was the awful. Had a different fish dish on JAL that was great but that pasta was a mish-mash of too many random things that didn't make sense plus dry fish. Staff was friendly and helpful.

Very noisy and careless crew on this overnight flight. They should understand customers want to sleep

The flight was delayed for 30 mins. The overall experience was good.

Highly impressive. On time. Smooth and fast boarding and disembarkment. Really great service

Overall, it was ok. However, the food was very sub-par.

The economy seats are much indeed roomier. Meals needs improvement.

It was okay overall but the food was very, very bad.

When comes to Taiwan airlines China airlines is the best rest are pure trash

Horrible. No good food. Baggage missed to onboard and came after a day. No support to compensate the delay. Customer care cannot see the status of the complaint. No reply of the email.

Food was hood for airline food with good poftion and variety in meals. Frequency of beverage service was very low and amount of soda with meals was inadequate.

bad… no veg food was provided eventhough i pre ordered special meal

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

Cramped seats. Audio jack for the in -flight entertainment was broken.

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.
10-3Mon
1 stopCathay Pacific
25h 35mSIN-ORD
18-3Tue
1 stopCathay Pacific
25h 00mORD-SIN
S$ 1,275
3-3Mon
1 stopCathay Pacific
30h 45mSIN-ORD
10-3Mon
1 stopCathay Pacific
25h 00mORD-SIN
S$ 1,280
10-2Mon
1 stopCathay Pacific
30h 45mSIN-ORD
18-2Tue
1 stopCathay Pacific
31h 15mORD-SIN
S$ 1,293
9-2Sun
2 stops
36h 23mSIN-ORD
18-2Tue
2 stops
29h 15mORD-SIN
S$ 1,320
9-2Sun
2 stops
36h 23mSIN-ORD
18-2Tue
3 stops
35h 05mORD-SIN
S$ 1,347
5-2Wed
1 stopUnited Airlines
42h 20mSIN-ORD
7-2Fri
2 stopsUnited Airlines
31h 25mORD-SIN
S$ 1,420
10-3Mon
1 stopEVA Air
41h 50mSIN-ORD
13-3Thu
1 stopEVA Air
25h 00mORD-SIN
S$ 1,440
11-3Tue
1 stopEVA Air
20h 20mSIN-ORD
17-3Mon
1 stopEVA Air
22h 35mORD-SIN
S$ 1,451
5-2Wed
3 stopsUnited Airlines
40h 59mSIN-ORD
7-2Fri
1 stopUnited Airlines
23h 45mORD-SIN
S$ 1,485
2-3Sun
2 stopsJapan Airlines
28h 57mSIN-ORD
10-3Mon
2 stopsJapan Airlines
27h 35mORD-SIN
S$ 2,105

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.
18-2Tue
3 stops
39h 47mSIN-MDW
S$ 684
20-2Thu
2 stops
28h 13mSIN-ORD
S$ 697
8-4Tue
3 stops
59h 00mSIN-ORD
S$ 704
28-1Tue
1 stopCathay Pacific
30h 45mSIN-ORD
S$ 798
28-1Tue
1 stopCathay Pacific
25h 35mSIN-ORD
S$ 800
27-1Mon
1 stopEVA Air
20h 20mSIN-ORD
S$ 886
29-1Wed
2 stopsEVA Air
28h 09mSIN-ORD
S$ 1,092
31-3Mon
3 stopsUnited Airlines
30h 55mSIN-ORD
S$ 1,259
4-4Fri
3 stopsUnited Airlines
28h 15mSIN-ORD
S$ 2,016
28-2Fri
1 stopANA
30h 45mSIN-ORD
S$ 4,659

Search by stops

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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.
24-1Fri
multi-stopUnited Airlines
26h 47mSIN-ORD
31-1Fri
multi-stopUnited Airlines
39h 40mORD-SIN
S$ 1,584
24-1Fri
multi-stopUnited Airlines
28h 05mSIN-ORD
1-2Sat
multi-stopUnited Airlines
23h 45mORD-SIN
S$ 1,613
24-1Fri
multi-stopLufthansa
38h 10mSIN-ORD
1-2Sat
multi-stopLufthansa
29h 40mORD-SIN
S$ 1,667
25-1Sat
multi-stopUnited Airlines
21h 10mSIN-ORD
31-1Fri
multi-stopUnited Airlines
33h 10mORD-SIN
S$ 1,683
25-1Sat
multi-stopCathay Pacific
30h 45mSIN-ORD
31-1Fri
multi-stopCathay Pacific
25h 00mORD-SIN
S$ 1,689
24-1Fri
multi-stopUnited Airlines
25h 19mSIN-ORD
31-1Fri
multi-stopUnited Airlines
33h 10mORD-SIN
S$ 1,697
23-1Thu
multi-stopCathay Pacific
25h 35mSIN-ORD
31-1Fri
multi-stopCathay Pacific
25h 00mORD-SIN
S$ 1,709
23-1Thu
multi-stopCathay Pacific
25h 35mSIN-ORD
1-2Sat
multi-stopCathay Pacific
32h 25mORD-SIN
S$ 1,731
24-1Fri
multi-stopAir India
24h 30mSIN-ORD
31-1Fri
multi-stopAir India
30h 00mORD-SIN
S$ 1,786
25-1Sat
multi-stopEVA Air
28h 09mSIN-ORD
1-2Sat
multi-stopEVA Air
33h 10mORD-SIN
S$ 2,523

Search by stops

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Search by price

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.

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