S$ 781 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 21-3. 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
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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
15:15 - 05:46SIN-ORD
27h 31m2 stops
14:58 - 13:50ORD-SIN
33h 52m3 stops
S$ 1,133
Find Deal
Tue, 8 Apr - Tue, 15 Apr
07:30 - 09:40SIN-ORD
39h 10m1 stop
12:20 - 19:55ORD-SIN
42h 35m1 stop
S$ 1,205Korean Air
Find Deal
Tue, 8 Apr - Tue, 15 Apr
22:20 - 06:13SIN-ORD
21h 53m1 stop
18:15 - 07:00ORD-SIN
23h 45m1 stop
S$ 1,235United Airlines
Find Deal
Wed, 5 Mar - Sun, 16 Mar
20:40 - 11:36SIN-ORD
27h 56m1 stop
06:30 - 18:25ORD-SIN
22h 55m1 stop
S$ 1,250United Airlines
Find Deal
Sun, 6 Apr - Sun, 13 Apr
01:50 - 14:25SIN-ORD
25h 35m1 stop
16:00 - 05:30ORD-SIN
24h 30m1 stop
S$ 1,254Cathay Pacific
Find Deal
Thu, 1 May - Mon, 5 May
20:15 - 14:00SIN-ORD
30h 45m1 stop
15:40 - 05:40ORD-SIN
25h 00m1 stop
S$ 1,264Cathay Pacific
Find Deal
Wed, 19 Mar - Wed, 26 Mar
11:00 - 22:20SIN-MDW
25h 20m2 stops
09:25 - 00:10MDW-SIN
25h 45m2 stops
S$ 1,280Delta
Find Deal
Wed, 5 Mar - Sun, 16 Mar
11:00 - 23:56SIN-ORD
26h 56m2 stops
06:15 - 05:00ORD-SIN
33h 45m2 stops
S$ 1,280Delta
Find Deal
Wed, 5 Mar - Sun, 16 Mar
15:45 - 19:35SIN-ORD
41h 50m1 stop
00:30 - 12:05ORD-SIN
22h 35m1 stop
S$ 1,360EVA Air
Find Deal
Wed, 5 Mar - Sat, 15 Mar
13:15 - 20:35SIN-ORD
20h 20m1 stop
00:30 - 12:05ORD-SIN
22h 35m1 stop
S$ 1,587EVA Air
Find Deal
Wed, 19 Mar - Tue, 25 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$ 1,590. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,351 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 February, where tickets cost S$ 1,445 on average for return flights. On the other hand, the most expensive months are August and January, where the average cost of tickets from Singapore is S$ 1,984 and S$ 1,933 respectively. For one-way flights, the best month to travel is February with an average price of S$ 1,445.

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$ 1,527 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$ 1,776.

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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 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$ 487.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 781
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly (4% 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 February.
  • 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, +75 more

ANA, Aer Lingus, +76 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, +78 more

ANA, Aer Lingus, +79 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, +75 more

ANA, Aer Lingus, +76 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, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Top 4 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 1200 reviews
8.0Food
8.6Crew
8.0Entertainment
8.4Boarding
8.3Comfort
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

Excellent food. Good service. Crammed Premium Economy seats. I Asked to change seats during check in. They told me the flight was fully booked. But on board I saw empty seats where I could have been easily relocated.

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.

EVA air was nice. It was the first time I’ve flown with them. The poor entertainment choices for 2 long flights will make me think about choosing them next time. I didn’t know if would effect me so much but I couldn’t sleep and it added to the stress. The food was terrible for me but I couldn’t find how to inform them about my diet when I bought my ticket.

I think the business class service has declined as compared to how it was years ago. I am not a fan of the hello kitty graphics. Boarding was long and not well organized. The lounge in Taipei was not very good, the food was very poor. Did not live up to many international business class lounges.

Boarding was good. It will be nice to have beer anytime. I asked for a beer at tea time & I was refused. Quite disappointed

The employees were professional and efficient. I consider myself a traveler but have trouble with the international fare served on airplanes. I admit Americans buy their food in the supermarket and we typically don’t eat the ligaments and cartilage. I know that is whiny but as I age, I dislike it more. At least things weren’t covered in cheese. The desserts are terrible! My neighbor didn’t eat her bread so I asked if I could have it. First time for everything but had been traveling a total of 27 hours and was hungry.

Amazing crew, excellent food, business class seats seem a bit dated but are super comfy even for a very tall person. If continuing onto Taipei, the stopover in Bangkok is a bit annoying (queue at security) though the lounge is decent.

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

Only one Hindi movie from LA to Taipei and same movie from Taipei to Singapore Why we call it entertainment when I have to watch one movie for 18 hours flying ?

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.

Crew was great. But a bit understaffed. The business class seat, etc were dated. But comfortable. Some legs had entertainment system from a decade ago. Selections were rather poor. Food was mediocre at best. Actually poor for business class standards. I liked the lounge in Hong Kong. Showers were great. Food was nice.

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

Everything was fine and I have no complaints or things to note.

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.

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.

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

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

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

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.
8-4Tue
2 stops
27h 31mSIN-ORD
15-4Tue
3 stops
33h 52mORD-SIN
S$ 1,133
8-4Tue
1 stopKorean Air
39h 10mSIN-ORD
15-4Tue
1 stopKorean Air
42h 35mORD-SIN
S$ 1,205
5-3Wed
1 stopUnited Airlines
21h 53mSIN-ORD
16-3Sun
1 stopUnited Airlines
23h 45mORD-SIN
S$ 1,235
6-4Sun
1 stopUnited Airlines
27h 56mSIN-ORD
13-4Sun
1 stopUnited Airlines
22h 55mORD-SIN
S$ 1,250
1-5Thu
1 stopCathay Pacific
25h 35mSIN-ORD
5-5Mon
1 stopCathay Pacific
24h 30mORD-SIN
S$ 1,254
19-3Wed
1 stopCathay Pacific
30h 45mSIN-ORD
26-3Wed
1 stopCathay Pacific
25h 00mORD-SIN
S$ 1,264
5-3Wed
2 stopsDelta
25h 20mSIN-MDW
16-3Sun
2 stopsDelta
25h 45mMDW-SIN
S$ 1,280
5-3Wed
2 stopsDelta
26h 56mSIN-ORD
16-3Sun
2 stopsDelta
33h 45mORD-SIN
S$ 1,280
5-3Wed
1 stopEVA Air
41h 50mSIN-ORD
15-3Sat
1 stopEVA Air
22h 35mORD-SIN
S$ 1,360
19-3Wed
1 stopEVA Air
20h 20mSIN-ORD
25-3Tue
1 stopEVA Air
22h 35mORD-SIN
S$ 1,587

Search by stops

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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.
21-3Fri
3 stops
37h 16mSIN-ORD
S$ 781
11-5Sun
2 stopsIndiGo
35h 10mSIN-ORD
S$ 782
11-4Fri
1 stopCathay Pacific
25h 35mSIN-ORD
S$ 797
11-4Fri
1 stopCathay Pacific
25h 35mSIN-ORD
S$ 798
9-5Fri
2 stopsDelta
38h 09mSIN-MDW
S$ 849
20-3Thu
2 stopsDelta
35h 23mSIN-ORD
S$ 849
4-8Mon
1 stopJapan Airlines
20h 20mSIN-ORD
S$ 1,381
4-8Mon
1 stopJapan Airlines
20h 20mSIN-ORD
S$ 1,384
12-4Sat
3 stopsUnited Airlines
31h 15mSIN-ORD
S$ 1,396
5-4Sat
1 stopUnited Airlines
29h 12mSIN-ORD
S$ 1,397

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.
25-2Tue
multi-stopUnited Airlines
28h 18mSIN-ORD
11-3Tue
multi-stopUnited Airlines
24h 00mORD-SIN
S$ 1,235
25-2Tue
multi-stopCathay Pacific
36h 55mSIN-ORD
11-3Tue
multi-stopCathay Pacific
25h 00mORD-SIN
S$ 1,314
25-2Tue
multi-stopCathay Pacific
36h 55mSIN-ORD
11-3Tue
multi-stopCathay Pacific
35h 40mORD-SIN
S$ 1,345
22-2Sat
multi-stopEVA Air
41h 50mSIN-ORD
1-3Sat
multi-stopEVA Air
22h 35mORD-SIN
S$ 1,417
22-2Sat
multi-stop
41h 50mSIN-ORD
1-3Sat
multi-stop
28h 09mORD-SIN
S$ 1,507
25-2Tue
multi-stop
36h 55mSIN-ORD
11-3Tue
multi-stop
35h 05mORD-SIN
S$ 1,599
25-2Tue
multi-stopEVA Air
20h 20mSIN-ORD
10-3Mon
multi-stopEVA Air
22h 35mORD-SIN
S$ 1,677
24-2Mon
multi-stop
25h 35mSIN-ORD
11-3Tue
multi-stop
39h 25mORD-SIN
S$ 1,818
24-2Mon
multi-stop
25h 35mSIN-ORD
11-3Tue
multi-stop
41h 55mORD-SIN
S$ 1,871
22-2Sat
multi-stopEVA Air
51h 07mSIN-ORD
1-3Sat
multi-stopEVA Air
32h 50mORD-SIN
S$ 1,912

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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