S$ 765 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 20-3. 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
In the last 7 days, travellers have searched 41,299,237 times on KAYAK, and here's why:

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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 from Singapore to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Singapore to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
22:20 - 17:05SIN-ORD
32h 45m1 stop
06:30 - 20:15ORD-SIN
23h 45m1 stop
S$ 1,334United Airlines
Find Deal
Tue, 21 Jan - Sun, 26 Jan
22:20 - 23:19SIN-ORD
38h 59m1 stop
15:50 - 20:15ORD-SIN
38h 25m1 stop
S$ 1,338United Airlines
Find Deal
Fri, 17 Jan - Fri, 24 Jan
01:30 - 00:11SIN-ORD
36h 41m2 stops
16:55 - 00:10ORD-SIN
41h 15m2 stops
S$ 1,353Delta
Find Deal
Mon, 20 Jan - Sun, 26 Jan
01:30 - 00:11SIN-ORD
36h 41m2 stops
16:58 - 00:10ORD-SIN
41h 12m2 stops
S$ 1,356Delta
Find Deal
Mon, 20 Jan - Sun, 26 Jan
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,365EVA Air
Find Deal
Sat, 26 Apr - Sun, 29 Jun
02:20 - 07:35SIN-ORD
19h 15m1 stop
10:35 - 17:25ORD-SIN
40h 50m1 stop
S$ 1,471Japan Airlines
Find Deal
Mon, 20 Jan - Sun, 26 Jan
02:20 - 07:35SIN-ORD
19h 15m1 stop
20:25 - 17:25ORD-SIN
31h 00m2 stops
S$ 1,502Japan Airlines
Find Deal
Mon, 20 Jan - Sun, 26 Jan
13:10 - 05:04SIN-ORD
28h 54m2 stops
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,800EVA Air
Find Deal
Sat, 26 Apr - Sun, 29 Jun
01:25 - 13:00SIN-ORD
25h 35m1 stop
14:40 - 05:40ORD-SIN
25h 00m1 stop
S$ 6,002Cathay Pacific
Find Deal
Sat, 15 Feb - Thu, 27 Feb
01:25 - 13:00SIN-ORD
25h 35m1 stop
14:40 - 16:20ORD-SIN
35h 40m2 stops
S$ 6,391Cathay Pacific
Find Deal
Sat, 15 Feb - Thu, 27 Feb

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$ 1,609. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,380 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$ 1,449 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$ 2,019 and S$ 1,909 respectively. For one-way flights, the best month to travel is October with an average price of S$ 1,449.

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$ 1,546 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$ 1,798.

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$ 468.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 765
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly (3% more expensive on average)
Flight from Singapore to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (14 km). You'll travel 26 km to reach the center of Chicago if you land in Chicago O'Hare Airport and 126 km if you land in Chicago Greater Rockford.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +74 more

ANA, Aer Lingus, +75 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +74 more

ANA, Aer Lingus, +75 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 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 1273 reviews
8.0Entertainment
8.4Boarding
8.6Crew
8.2Comfort
8.0Food
Airline reviews

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.

6.0 GoodMargaret, Nov 2024TPE - SFO
Read more EVA Air reviews

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.

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.

The food was good, but we are not able to use earphones to watch a movie.

I was expecting that movie selection and food would have been better. Everything else was great.

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.

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

Loved that leg room was great for economy, and food was definitely better than other American airlines, great selection of movies. My mom is happy.

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

ANA’s service was great, and the flight was nice and smooth . They gave us updates and checking in and boarding was smooth and easy .

I have never been a big fan of airplane meals

Flight was overall OK: lovely staff and smooth travelling. The only downside was no food was available on a 3.5 hour flight over lunchtime. Luckily we had realised this in advance and brought our own bento.

The whole flight in Economy was great, the crew were just amazing and the food was great as well

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.

I loved Ryuichi Sakamoto's OPUS in the movie choice.

Too bad the plane didn't work after we taxied out to get in line for take-off. We went back to the gate and waited for almost 90 minutes for them to find a plane that worked. Waited another hour to board. When we got to Rochester we waited for over an hour for our bags to appear. The agent said they only had three people working to load and unload baggage. A one hour flight took an extra four hours. It would have been faster to rent a car at JFK and drive to Rochester.

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

Excellent service provided the flight crew. Food and drinks were very good.

Cathay has a great reputation, though it's baseline economy seating is nothing to write home about (and SE Asia flight passengers sometime lack 'routine stateside' etiquette). On the other hand, food was great, flight attendants were nice, and price was very good~

Cathay was not the problem. The problem was the customer service from Kayak/Underprice. Will never book through Kayak again.

The crews were smiling all the time with soft tunes when they spoke; the food was excellent. Thank you!

They charged me $900 to board my flight I already paid for just because I missed my previous flight. I do not recommend this airline by any means.

Not good. Small seats. Not enough food that customers wanted. No special requests were given that i could see. Slow response from flight attendants

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.

Flight was great albeit the long line before the int’l immigration given the timing of the year.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

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.
21-1Tue
1 stopUnited Airlines
32h 45mSIN-ORD
26-1Sun
1 stopUnited Airlines
23h 45mORD-SIN
S$ 1,334
17-1Fri
1 stopUnited Airlines
38h 59mSIN-ORD
24-1Fri
1 stopUnited Airlines
38h 25mORD-SIN
S$ 1,338
20-1Mon
2 stopsDelta
36h 41mSIN-ORD
26-1Sun
2 stopsDelta
41h 15mORD-SIN
S$ 1,353
20-1Mon
2 stopsDelta
36h 41mSIN-ORD
26-1Sun
2 stopsDelta
41h 12mORD-SIN
S$ 1,356
26-4Sat
1 stopEVA Air
20h 50mSIN-ORD
29-6Sun
1 stopEVA Air
22h 30mORD-SIN
S$ 1,365
20-1Mon
1 stopJapan Airlines
19h 15mSIN-ORD
26-1Sun
1 stopJapan Airlines
40h 50mORD-SIN
S$ 1,471
20-1Mon
1 stopJapan Airlines
19h 15mSIN-ORD
26-1Sun
2 stopsJapan Airlines
31h 00mORD-SIN
S$ 1,502
26-4Sat
2 stopsEVA Air
28h 54mSIN-ORD
29-6Sun
1 stopEVA Air
22h 30mORD-SIN
S$ 1,800
15-2Sat
1 stopCathay Pacific
25h 35mSIN-ORD
27-2Thu
1 stopCathay Pacific
25h 00mORD-SIN
S$ 6,002
15-2Sat
1 stopCathay Pacific
25h 35mSIN-ORD
27-2Thu
2 stopsCathay Pacific
35h 40mORD-SIN
S$ 6,391

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.
20-3Thu
3 stops
53h 15mSIN-ORD
S$ 765
11-2Tue
3 stops
41h 51mSIN-ORD
S$ 766
30-1Thu
3 stops
33h 11mSIN-ORD
S$ 775
22-2Sat
1 stopCathay Pacific
25h 35mSIN-ORD
S$ 863
26-12Thu
1 stopCathay Pacific
25h 35mSIN-ORD
S$ 866
13-1Mon
2 stopsUnited Airlines
36h 05mSIN-ORD
S$ 1,265
30-1Thu
3 stopsUnited Airlines
39h 49mSIN-ORD
S$ 1,269
17-1Fri
1 stopJapan Airlines
37h 20mSIN-ORD
S$ 1,403
12-1Sun
2 stopsJapan Airlines
31h 11mSIN-ORD
S$ 1,418
11-1Sat
1 stopANA
22h 30mSIN-ORD
S$ 1,782

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.
19-12Thu
multi-stopUnited Airlines
24h 57mSIN-ORD
27-12Fri
multi-stopUnited Airlines
44h 00mORD-SIN
S$ 1,720
19-12Thu
multi-stopUnited Airlines
23h 49mSIN-ORD
27-12Fri
multi-stopUnited Airlines
44h 00mORD-SIN
S$ 1,855
20-12Fri
multi-stopUnited Airlines
27h 10mSIN-ORD
28-12Sat
multi-stopUnited Airlines
33h 08mORD-SIN
S$ 1,890
20-12Fri
multi-stopUnited Airlines
21h 34mSIN-ORD
28-12Sat
multi-stopUnited Airlines
32h 15mORD-SIN
S$ 1,905
19-12Thu
multi-stop
25h 23mSIN-ORD
27-12Fri
multi-stop
27h 31mORD-SIN
S$ 1,931
20-12Fri
multi-stopUnited Airlines
24h 15mSIN-ORD
28-12Sat
multi-stopUnited Airlines
32h 46mORD-SIN
S$ 2,129
20-12Fri
multi-stop
36h 55mSIN-ORD
28-12Sat
multi-stop
30h 25mORD-SIN
S$ 2,414
19-12Thu
multi-stop
35h 20mSIN-ORD
27-12Fri
multi-stop
39h 25mORD-SIN
S$ 2,548
19-12Thu
multi-stopCathay Pacific
25h 35mSIN-ORD
28-12Sat
multi-stopCathay Pacific
31h 15mORD-SIN
S$ 2,575
19-12Thu
multi-stop
25h 35mSIN-ORD
28-12Sat
multi-stop
30h 50mORD-SIN
S$ 2,620

Search by stops

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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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