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$570 Find cheap flights from Singapore 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 6/7. 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
0 bags
Mon 6/3
Mon 6/10

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
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

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

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

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Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for 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 Wednesday where tickets can be as cheap as $1,116. On the other hand, the most expensive day to fly is Sunday, where prices are $1,637 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 $1,094 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 $1,741 and $1,703 respectively. For return trips, the best month to travel is October with an average price of $1,094.

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 $1,240 on average. The most expensive time of day to fly to Chicago is generally at night, which is peak travel time and where the average cost of a ticket is $1,305.

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 Midway Airport, with an average flight price of $114.

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 82% 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 20m.

How many direct flights to Chicago are there each day?

There are around 1,572 direct flights from within Singapore to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 51% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,003 direct flights from within Singapore to Chicago. The most common day for departures is Tuesday, with 16% of flights taking off on this day.

Good to know

Low season

January

High season

May

Cheapest flight

$570
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Singapore to Chicago

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 (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles 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 travelers 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 5,222 per week, followed by American Airlines with 2,596 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 non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Singapore to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 3 airlines serving from Singapore 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.
8.3
EVA AirOverall score based on 1542 reviews
8.2Comfort
8.6Crew
8.0Entertainment
8.4Boarding
8.0Food
Airline reviews

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.

8.0 ExcellentAnonymous, Apr 2024TPE - JFK
Read more about EVA Air reviews

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

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

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!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Book cheap flights from Singapore to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
9/16Mon
1 stopAir India
35h 50mSIN-ORD
9/30Mon
1 stopAir India
30h 30mORD-SIN
$1,003
9/16Mon
1 stopDelta
35h 40mSIN-ORD
9/30Mon
2 stopsDelta
34h 00mORD-SIN
$1,098
6/25Tue
2 stopsAmerican Airlines
27h 05mSIN-ORD
7/10Wed
1 stopAmerican Airlines
28h 50mORD-SIN
$1,102
6/15Sat
2 stopsAmerican Airlines
24h 27mSIN-ORD
7/30Tue
1 stopAmerican Airlines
28h 50mORD-SIN
$1,104
7/9Tue
2 stopsJapan Airlines
58h 43mSIN-ORD
7/17Wed
1 stopJapan Airlines
28h 50mORD-SIN
$1,110
7/8Mon
2 stopsJapan Airlines
54h 43mSIN-ORD
7/17Wed
1 stopJapan Airlines
28h 50mORD-SIN
$1,133
8/5Mon
1 stopUnited Airlines
33h 11mSIN-ORD
1/16Thu
1 stopUnited Airlines
36h 00mORD-SIN
$1,281
5/25Sat
1 stopUnited Airlines
30h 45mSIN-ORD
7/29Mon
2 stopsUnited Airlines
28h 30mORD-SIN
$1,288
5/25Sat
2 stopsEVA Air
27h 12mSIN-ORD
7/28Sun
1 stopEVA Air
24h 20mORD-SIN
$1,330
5/25Sat
1 stopEVA Air
20h 50mSIN-ORD
7/28Sun
1 stopEVA Air
24h 20mORD-SIN
$1,505

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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.
6/7Fri
3 stops
59h 22mSIN-ORD
$570
6/6Thu
3 stops
41h 45mSIN-ORD
$574
6/6Thu
2 stops
47h 52mSIN-ORD
$632
6/7Fri
2 stops
43h 07mSIN-ORD
$650
6/7Fri
1 stopCathay Pacific
31h 15mSIN-ORD
$814
5/19Sun
1 stopSingapore Airlines
23h 30mSIN-ORD
$864
6/6Thu
1 stopCathay Pacific
25h 40mSIN-ORD
$955
5/18Sat
2 stopsAmerican Airlines
26h 55mSIN-ORD
$995
8/14Wed
1 stopAmerican Airlines
20h 30mSIN-ORD
$1,022
5/20Mon
3 stopsUnited Airlines
32h 29mSIN-ORD
$5,049

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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.
5/4Sat
multi-stopDelta
23h 41mSIN-MDW
5/11Sat
multi-stopDelta
34h 00mMDW-SIN
$2,091
5/6Mon
multi-stopUnited Airlines
29h 48mSIN-ORD
5/9Thu
multi-stopUnited Airlines
28h 50mORD-SIN
$4,372
5/6Mon
multi-stopAir India
35h 50mSIN-ORD
5/9Thu
multi-stopAir India
30h 30mORD-SIN
$4,451
5/5Sun
multi-stopEVA Air
20h 50mSIN-ORD
5/8Wed
multi-stopEVA Air
24h 20mORD-SIN
$5,533
5/5Sun
multi-stopCathay Pacific
20h 55mSIN-ORD
5/9Thu
multi-stopCathay Pacific
30h 50mORD-SIN
$5,534
5/6Mon
multi-stopEVA Air
20h 50mSIN-ORD
5/8Wed
multi-stopEVA Air
22h 30mORD-SIN
$5,723
5/5Sun
multi-stop
27h 39mSIN-ORD
5/9Thu
multi-stop
34h 00mORD-SIN
$5,831
5/5Sun
multi-stopEVA Air
51h 14mSIN-ORD
5/8Wed
multi-stopEVA Air
24h 20mORD-SIN
$6,019
5/6Mon
multi-stopUnited Airlines
27h 59mSIN-ORD
5/9Thu
multi-stopUnited Airlines
29h 45mORD-SIN
$6,254
5/5Sun
multi-stopAmerican Airlines
28h 29mSIN-ORD
5/9Thu
multi-stopAmerican Airlines
32h 50mORD-SIN
$6,704

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Flights to Chicago

Return flight deals:

Chicago - Singapore

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