$495 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 2/25. 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
1 adult, Economy, 0 bags

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
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$899
Typical prices: $915-$1,026
Multiple Airlines
Thu 2/26Thu 3/5
SIN - ORD • 2 stops
Cheapest one-way
$495
Multiple Airlines
Wed 2/25
SIN - MDW • 3 stops
When to travel
September
Cheapest • 22% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Singapore to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Singapore 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 round-trip flight deals from Singapore to Chicago

Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
2:25 pm - 2:11 pm
SIN
-
ORD
37h 46m
2 stops
Multiple Airlines Logo
5:29 pm - 1:05 pm
ORD
-
SIN
29h 36m
2 stops
$899Multiple Airlines
Mon, Jan 26 - Thu, Jan 29
Multiple Airlines Logo
2:25 pm - 2:38 pm
SIN
-
ORD
38h 13m
2 stops
Multiple Airlines Logo
6:06 pm - 1:05 pm
ORD
-
SIN
28h 59m
2 stops
$901Multiple Airlines
Wed, Feb 25 - Wed, Mar 4
Japan Airlines Logo
10:25 pm - 7:35 am
SIN
-
ORD
23h 10m
1 stop
Japan Airlines Logo
5:40 pm - 6:35 am
ORD
-
SIN
22h 55m
1 stop
$930Japan Airlines
Wed, Feb 25 - Thu, Mar 5
Japan Airlines Logo
2:20 am - 7:35 am
SIN
-
ORD
19h 15m
1 stop
Japan Airlines Logo
6:00 am - 12:50 am
ORD
-
SIN
28h 50m
2 stops
$933Japan Airlines
Tue, Feb 17 - Wed, Feb 18
United Airlines Logo
10:20 pm - 6:19 am
SIN
-
ORD
21h 59m
1 stop
United Airlines Logo
9:01 am - 8:00 am
ORD
-
SIN
32h 59m
1 stop
$934United Airlines
Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
10:25 pm - 7:35 am
SIN
-
ORD
23h 10m
1 stop
Multiple Airlines Logo
3:54 pm - 1:00 pm
ORD
-
SIN
31h 06m
2 stops
$935Multiple Airlines
Thu, Feb 26 - Thu, Mar 5
United Airlines Logo
10:10 am - 7:55 pm
SIN
-
ORD
23h 45m
1 stop
United Airlines Logo
6:17 am - 8:15 pm
ORD
-
SIN
23h 58m
1 stop
$937United Airlines
Sun, Jun 28 - Fri, Aug 7
United Airlines Logo
8:40 pm - 4:58 am
SIN
-
ORD
21h 18m
1 stop
United Airlines Logo
6:02 am - 6:35 pm
ORD
-
SIN
23h 33m
1 stop
$939United Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
10:30 pm - 12:46 pm
SIN
-
MDW
28h 16m
2 stops
Delta Logo
6:40 pm - 8:25 pm
MDW
-
SIN
35h 45m
2 stops
$962Delta
Wed, Feb 25 - Wed, Mar 4
Delta Logo
10:40 am - 9:54 am
SIN
-
MDW
37h 14m
2 stops
Delta Logo
6:00 am - 12:10 am
MDW
-
SIN
28h 10m
2 stops
$963Delta
Booking Insights

KAYAK's insights & trends for flights to Chicago

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 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 September, where tickets cost $847 on average for one-way flights. On the other hand, the most expensive months are January and June, where the average cost of tickets from Singapore is $1,581 and $1,195 respectively. For return trips, the best month to travel is September with an average price of $847.

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 Greater Rockford Airport, with an average flight price of $122.

Good to know

Low seasonJanuary
Best time to beat the crowds but there is an average 45% increase in price.
Most popular time to fly with an average 9% increase in price.

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.

  • How many direct flights to Chicago are there each week?

    Each week there are around 7,976 direct flights from within Singapore to Chicago. The most common day for departures is Monday, with 15% of flights taking off on this day.

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.

Reviews of the top airlines flying 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.
7.6
Cathay PacificOverall score based on 1128 reviews
8.1Crew
7.8Entertainment
7.3Food
7.9Boarding
7.6Comfort
Airline reviews

The bed was alright in business class. Food variety and quality were not up to the mark compared to the business class airfare.

6.0 GoodAnonymous, Jan 2026
HKG - JFK
Read more Cathay Pacific reviews

The bed was alright in business class. Food variety and quality were not up to the mark compared to the business class airfare.

Food , drink experience were great with Cathay. Crew service was excellent. Clean toilet and full snack bars always, pilot took of 26minutes later when boarding at Hong Kong with extra US customs check at gate 9 for US flight, but he managed to arrive only 2 minutes later from flight tracker. Smooth flight .

I wish there were more bathrooms available on these larger carriers.

one hour transit not good. cathay pacific is not helpful at all

My flight was suppose to be at 7:45pm to fly but it didnt fly out until 8:55 to dallas so then all of my other flights was late and delay ihad to wait at the airport for extra 14 hours to be able to get on a different plane

The flight was just ok, but the vendor made it exceptio ally bard to manage my own reservation and would not give me access. The blocked all of the one time pins to come to their email address which caused me.to go through them eceryrime to get seats see rhe reservation and even get wheelchair access for my sick 71 year old uncle. They only xommunicates via a bot which gave me incorrect info. I thought this was Kayak and not underprivileged. They ruined his trip, did not get him aisle seats and made it impossible to purchase extra leg room. It was a horrible experience. He was taken to hospital on arrival only to find he had blood clots and pnemonia while trying to navigate the airport. This vendor is very irresponsible and the airline could not access his info.

Super delayed. Unnecessary. Need more competent people doing logistics to keep things moving on time. Totally unacceptable.

Overall, not good. Super late boarding in Hong Kong because some last minute issue with a plane. The boarding process is chaotic. Kathy Pacific should seek to do better with punctual departure time. Caused a lot of trouble with missed connecting flight.

Not much of anything could have been done better unless I had a first class ticket. I was literally 15 hours with an airline in the economy class. Very professional friendly and attentive crew. Good airline food, clean cabin, seating area and bathrooms. I've been 4 times back-and-forth with Cathay Pacific, and I would not choose another airline for this trip. Five out of five stars.

Well- trained, cheerful onboard staff. Business class seating and storage were excellent. Outstanding range of food choices, though quality ranged from just OK (seasonal rice and beef dish) to outstanding ( congee and soup noodles with beef brisket). But what can you expect; it's on a plane. I couldn't figure out the remote control, but touch screen worked well. My wife and I (in our 60s), didnt find much to watch from the Entertainment choices. We mostly watched the flight maps. The bedding did the job but is unwieldy and ends up in a clump, with one-third falling on the floor.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

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.