S$ 628 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 29-5. 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.
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KAYAK searches 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

KAYAK's recommended return flight deals from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Air Canada Logo
09:10 - 14:49SIN-ORD
42h 39m1 stop
Air Canada Logo
20:03 - 07:05ORD-SIN
46h 02m2 stops
S$ 1,175Air Canada
Find Deal
Tue, 24 Jun - Wed, 23 Jul
Air Canada Logo
09:10 - 14:49SIN-ORD
42h 39m1 stop
Air Canada Logo
20:03 - 07:05ORD-SIN
46h 02m2 stops
S$ 1,177Air Canada
Find Deal
Tue, 24 Jun - Wed, 23 Jul
United Airlines Logo
20:40 - 05:11SIN-ORD
21h 31m1 stop
United Airlines Logo
18:25 - 06:45ORD-SIN
23h 20m1 stop
S$ 1,232United Airlines
Find Deal
Fri, 2 May - Tue, 6 May
United Airlines Logo
20:40 - 05:11SIN-ORD
21h 31m1 stop
United Airlines Logo
20:30 - 18:25ORD-SIN
32h 55m1 stop
S$ 1,240United Airlines
Find Deal
Mon, 12 May - Sat, 17 May
Cathay Pacific Logo
20:05 - 14:25SIN-ORD
31h 20m1 stop
Cathay Pacific Logo
16:00 - 11:45ORD-SIN
30h 45m1 stop
S$ 1,317Cathay Pacific
Find Deal
Thu, 1 May - Tue, 6 May
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
S$ 1,373Cathay Pacific
Find Deal
Thu, 1 May - Thu, 8 May
Japan Airlines Logo
08:05 - 16:00SIN-ORD
20h 55m1 stop
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
S$ 1,476Japan Airlines
Find Deal
Fri, 6 Jun - Tue, 10 Jun
Japan Airlines Logo
08:05 - 16:00SIN-ORD
20h 55m1 stop
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
S$ 1,484Japan Airlines
Find Deal
Fri, 6 Jun - Tue, 10 Jun
EVA Air Logo
13:10 - 21:00SIN-ORD
20h 50m1 stop
EVA Air Logo
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,598EVA Air
Find Deal
Fri, 2 May - Fri, 2 May
EVA Air Logo
13:10 - 21:00SIN-ORD
20h 50m1 stop
EVA Air Logo
18:22 - 13:50ORD-SIN
30h 28m2 stops
S$ 1,702EVA Air
Find Deal
Mon, 23 Jun - Tue, 8 Jul

KAYAK's insights & trends for flights to Chicago

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$ 1,588. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,349 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$ 1,341 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$ 1,992 and S$ 1,931 respectively. For one-way flights, the best month to travel is February with an average price of S$ 1,341.

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$ 1,142 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$ 1,328.

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 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 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$ 433.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

High season

December

Cheapest flight

S$ 628
Best time to beat the crowds but there is an average 20% 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

  • 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, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 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 1172 reviews
8.3Comfort
8.4Boarding
8.6Crew
8.1Food
8.0Entertainment
Airline reviews

Sub sandwhich for a snack through mid flight and giving a bottle water was a good idea

8.0 ExcellentAnonymous, Mar 2025TPE - IAH
Read more EVA Air reviews

Sub sandwhich for a snack through mid flight and giving a bottle water was a good idea

seats are pitched well. you don't feel too tight.

For the price, it was better than other airlines; quality of food and service was very good.

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.

delayed and the cabin crew was like trainees.. a bit careless and not so pleasing to their job

Except for crying babies all was ok although the movie selection wasn't the best.

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.

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

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.

So so, crew was overly professional and lacks human touch. Equipment is very old, especially the HKG-PVG CX366 flight. That plane along with its decor must have twenty years of history, or at least I had that impression.

very professional and very attentive to my Special Needs as I required a Wheel Chair and assistance to board

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.

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

flight delayed 45 mins - missed connection - 1 hr layover became 8 hr layover waiting for next flight -

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

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.

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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