Cheap Flights from Singapore to Chicago

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Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Singapore to Chicago

Looking for a cheap last-minute deal or the best return flight from Singapore to Chicago? If you want to travel next month, return fares start from R 13,702. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Singapore to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Singapore to Chicago flights are currently cheapest in September.

Alternative Singapore to Chicago routes

Looking for the cheapest, fastest or easiest route from Singapore to Chicago? You could fly into the following airports instead.

Singapore to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 8,288
Cheapest month to flySeptember

Finding cheap flights from Singapore to Chicago: Frequently asked questions

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from Singapore to Chicago is R 11,960. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Singapore to Chicago. But we found flights with one or more stops from R 11,960.
As of July 2026, there are no flights flying from Singapore to Chicago.
The cheapest month to fly from Singapore to Chicago is usually February.
If you're flying from Singapore, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from R 11,960.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Singapore to Chicago on Thursday, 4 February 2027.
No airlines currently offer direct flights between Singapore and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is Air Canada .

Travelling from Singapore to Chicago: what you need to know

  • There are a couple of main airports to choose from in Singapore. Check out your options departing from Singapore Changi Airport (SIN) or Seletar Airport (XSP) when searching for a flight from Singapore to Chicago.

  • Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW) are Chicago's primary gateways.

  • The timezone in Chicago is UTC-6, which is 14 hours behind Singapore.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your Singapore to Chicago flight.

  • You can expect longer queues during popular months such as June. Arriving up to four hours in advance for international flights and two hours for domestic departures is a wise move.

How to find the cheapest flights from Singapore to Chicago

  • To find cheap Singapore to Chicago flights, book in advance. Airlines typically offer the most competitive fares when tickets are first released.

  • If you can be flexible with your travel plans, try using the 'Whole month' tool. It'll show you the cheapest price across the month when looking for your plane ticket from Singapore to Chicago.

  • Spend less time searching for cheap flights from Singapore to Chicago by setting up a Price Alert. You'll get an email or notification on the app when a new low fare is offered.

  • Select your ideal departure and arrival times, airlines and number of stops with the filters. Or sort your Singapore to Chicago flight results by 'Best,' 'Fastest' or 'Cheapest.'

Flying from Singapore

Singapore Changi Airport (SIN)

  • Consider adding a stopover to potentially find a cheaper Singapore to Chicago flight. Just uncheck 'Direct flights only' when browsing departures from Singapore Changi Airport. Take a pause at one of these airports:

    • Los Angeles International Airport (LAX)

    • Tokyo Haneda Airport (HND)

    • Seattle / Tacoma International Airport (SEA)

  • The journey from central Singapore to SIN takes around 40 minutes by public transport. If you drive, ride-share or take a taxi, you'll cover the 18 kilometres in 25 minutes or so, depending on traffic conditions.

  • Want an easy start to your journey? Stay near Singapore Changi Airport. Whether you're catching an early flight from Singapore to Chicago or want to avoid feeling rushed, these hotels are ideal:

  • When it comes to Singapore Changi Airport's on-time performance, 74% of flights meet their scheduled arrival time.

Seletar Airport (XSP)

  • XSP is about 14 kilometres from central Singapore. It'll take 25 minutes or so to get to the airport if you're driving from the city centre. Public transport takes roughly 1 hour.

  • Start your holiday early with an additional night away from home. Before catching your flight from Singapore to Chicago, unwind in one of these hotels close to Seletar Airport:

  • Flights from Seletar Airport have a track record for punctuality, with 82% of them landing right on cue.

Arriving in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to central Chicago takes about 30 minutes to reach by car. The centre is roughly 26 kilometres away.

  • When travelling on public transport, expect a journey time of around 45 minutes.

  • If you're coming in on a late flight from Singapore to Chicago, nothing beats the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and resting soon after at one of these accommodation options near ORD:

  • Travel at your own pace with a Chicago O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and experience more of Chicago and beyond.

  • To lock in the lowest price, reserve your ride from Chicago O'Hare International Airport about four weeks in advance of your Singapore to Chicago flight.

  • ORD is located at 10000 West O'Hare.

Chicago Midway Airport (MDW)

  • The centre of Chicago is about 14 kilometres from Chicago Midway Airport (MDW). After your flight from Singapore to Chicago has touched down and you've made your way through the terminal, expect a drive of around 25 minutes.

  • Public transport will get you there in around 30 minutes.

  • Hang up the 'Do not disturb' sign and relax at a hotel near MDW. Here are a few options where you can put your feet up after your flight from Singapore to Chicago:

  • The fastest way to get to where you're going is with a Chicago Midway Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and get going in the blink of an eye.

  • Score the best price by booking your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • The address for Chicago Midway Airport is 5700 South Cicero.

Chicago Rockford Airport (RFD)

  • Make your way into the city centre after your flight from Singapore to Chicago has touched down. Central Chicago is about 129 kilometres from Chicago Rockford Airport (RFD) and takes roughly 1 hour 40 minutes to get there in a car.

  • The journey will take you around 2 hours when travelling by public transport.

  • Whether you want a zippy compact for a solo adventure or a full-size SUV to fit a group of friends, you'll find the perfect Chicago Rockford Airport rental car for your needs. Explore the types of wheels available here from providers such as Budget, Alamo and National.

  • If you prefer a particular type of vehicle, booking early gives you a better shot at getting your first choice. Book your ride from RFD a couple of weeks ahead of your flight from Singapore to Chicago.

  • Chicago Rockford Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • It's time to plan your dates for your flight from Singapore to Chicago. July is the busiest month to travel to Chicago. If you like a more relaxed vibe, go in March.

  • Lock in a Singapore to Chicago ticket departing in July if you want to experience the city during its warmest month. You can expect temperatures in Chicago to range from 16ºC (61ºF) to 28ºC (82ºF).

  • Search for cheap flights from Singapore to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Explore these hotels once you've booked your flight from Singapore to Chicago:

  • There are so many things to discover in this city it can be hard to figure out where to begin. Millennium Park, The Art Institute of Chicago and Willis Tower are top sights which should feature on any good Chicago itinerary.

Explore more of the United States

  • Columbus is just one of the many places in the United States waiting to be discovered once you've seen the sights of Chicago. Around 451 kilometres to the southeast, its top attractions include Franklin Park Conservatory and Botanical Gardens, Columbus Park of Roses and Ohio Theatre.

  • Around 257 kilometres southeast of Chicago, Indianapolis is another favourite stop in the United States. Get a taste of what this destination has to offer at Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.