S$ 625 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 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.
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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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Flights Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Mon, 23 Jun - Tue, 22 Jul
Japan Airlines Logo
01:55 - 19:29SIN-ORD
30h 34m2 stops
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
S$ 870Japan Airlines
Find Deal
Mon, 23 Jun - Tue, 22 Jul
Japan Airlines Logo
01:55 - 19:29SIN-ORD
30h 34m2 stops
Japan Airlines Logo
01:30 - 17:30ORD-SIN
27h 00m1 stop
S$ 871Japan Airlines
Find Deal
Sun, 26 Oct - Thu, 13 Nov
Korean Air Logo
01:30 - 09:30SIN-ORD
21h 00m1 stop
Korean Air Logo
11:05 - 00:10ORD-SIN
23h 05m1 stop
S$ 1,240Korean Air
Find Deal
Sun, 26 Oct - Thu, 13 Nov
Korean Air Logo
01:30 - 09:30SIN-ORD
21h 00m1 stop
Korean Air Logo
11:05 - 05:00ORD-SIN
27h 55m1 stop
S$ 1,249Korean Air
Find Deal
Sun, 6 Jul - Sun, 13 Jul
United Airlines Logo
20:40 - 05:18SIN-ORD
21h 38m1 stop
United Airlines Logo
12:46 - 06:15ORD-SIN
28h 29m1 stop
S$ 1,358United Airlines
Find Deal
Sat, 9 Aug - Mon, 11 Aug
EVA Air Logo
13:10 - 23:59SIN-ORD
47h 49m2 stops
EVA Air Logo
13:03 - 12:00ORD-SIN
33h 57m2 stops
S$ 1,393EVA Air
Find Deal
Mon, 16 Jun - Sat, 28 Jun
EVA Air Logo
15:10 - 05:40SIN-ORD
27h 30m2 stops
EVA Air Logo
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,395EVA Air
Find Deal
Sun, 15 Jun - Sun, 29 Jun
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
S$ 1,479Cathay Pacific
Find Deal
Tue, 17 Jun - Fri, 27 Jun
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
S$ 1,499Cathay Pacific
Find Deal
Thu, 7 Aug - Fri, 8 Aug
United Airlines Logo
08:45 - 00:59SIN-ORD
29h 14m1 stop
United Airlines Logo
16:07 - 06:15ORD-SIN
25h 08m2 stops
S$ 1,635United Airlines
Find Deal
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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 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 April, where tickets cost S$ 1,206 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$ 1,928 and S$ 1,866 respectively. For one-way flights, the best month to travel is April with an average price of S$ 1,206.

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 Midway Airport (MDW), with an average flight price of S$ 256.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
High seasonJune
Cheapest flightS$ 625
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly (5% 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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as S$ 1,535. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are S$ 2,270 on average.

  • 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.

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

    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.

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, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 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 1195 reviews
8.1Food
8.4Boarding
8.3Comfort
8.0Entertainment
8.6Crew
Airline reviews

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. Oh and the seats were more comfortable, had more ability to lean and the headrest was much better for flight sleeping. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

10.0 ExcellentAnonymous, May 2025TPE - SEA
Read more EVA Air reviews

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. Oh and the seats were more comfortable, had more ability to lean and the headrest was much better for flight sleeping. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

I have never heard of EVA air before but I am so happy my wife and I were able to flight on their planes twice. Everything on these flights just felt better than their competitors. As someone with longer legs any bit of extra leg spaces is appreciated. The different options for food and drinks were also a plus. They were extra careful to make sure my wife's eating restrictions were taken care for. They had a before take off and landing announcements on the built in tablets for each seat and it gave out information that was very helpful. Such as what and how to declare your items in the specific country you landed in, any odd items that may be illegal to bring it (and even the reasoning why) and any other information you might need to make your post flight experience better. The only downside was there were "forced" ads on the tablet at take off for maybe 5-10 minutes but honestly, this flight was the cheapest option and had all the benefits listed above that is such an easy trade off. Im keeping an eye out for EVA air going forward.

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

The flight attendants should be nicer, on my first flight I told them I’d prefer a veggie meal sometimes and then she began to lecture me about it, it was a late flight and I wanted an easy digestion meal so that I can sleep quickly. The meals were abit odd, breakfast on my last flight had eggs, oatmeal and fish, did not taste good at all, strange combination. The economy seats are very tight and crowded, not comfortable at all. Overall for the price I paid I thought I was going to get more.

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.

Movie selection was not as good as recent flights I've taken (EVA and other airlines).

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

Flight from New Delhi to Tokyo was mediocre. The seats were not of business class as we are used to. They were not wide enough. On the other hand the seats on the flight from Tokyo to San Francisco were excellent every thing were great except the food. Tokyo business lounge was excellent. The whole experience was great except the food on the plane. Will still fly JAL.

The entree wasn’t very good. The rice was soggy. The side dishes were all good though. The breakfast was also good. The crew were excellent, as usual.

The flight attendants were excellent as usual however the meal wasn’t the usual good quality. There is cooked rice was mushy.

This portion of the trip from HCMC to Dallas was operated by American Airline. Unfortunately they are 2 steps below JAL in overall quality. Regardless, AAStill got me where I needed to go on time.

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

The food and service was great. You have to pay a lot for in flight Internet though which is lame.

Flight was delayed at the last minute for six hours. Instead of delaying it to a normal hour, they moved it to 10 pm to essentially make it a redeye. There was no compensation or benefit offered for this inconvenience. Once on the plane, Inpaid for WiFi twice with both times it not working because of a “weak WiFi signal”, according to the flight attendants. They also chose the farther possible gates in both airports from the entrance/exit, even though they were one of the few active flights left so late in the evening. Overall it was pretty horrible.

Special request meals are really below average. Vegetarian options are very limited if you didn't prebook.

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

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

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

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

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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