$514 Cheap Flights from Singapore (SIN) to Chicago (ORD)

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Singapore (SIN) to Chicago (ORD) at a glance

Embark on an international journey from Singapore (SIN) to Chicago (ORD) with a selection of airlines offering diverse flight options. Whether you seek cheap flights from SIN or prefer full-service carriers, you can compare itineraries to find the best fit for your budget and schedule. Gather essential information for your SIN to ORD flight and prepare to explore the iconic sights and vibrant neighborhoods of Chicago.

• Fastest flight duration: around 19 hours in-flight, plus roughly 2h 15m layover with one stop
• Route distance: roughly 9,400 miles (15,130 km)
• Flights per week: around 9 departures on average
• Typical fares (one-way): economy tickets often range from $495–$1400, depending on seasonality and how far ahead you book

Flights from Changi Airport (SIN) to O'Hare International Airport (ORD)

According to the latest traveler bookings, here are the top airlines favored for flights from Singapore to Chicago, particularly for one-stop and multi-stop journeys. Common layover points include San Francisco International Airport (SFO) with around a 2-hour layover, Incheon International Airport (ICN) offering approximately 4 hours and 45 minutes, and Taoyuan International Airport (TPE) with about 2 hours and 15 minutes. This variety allows you to customize your itinerary by balancing price, total travel time, and cabin class.

• United: This comprehensive airline provides one-stop service, with one-way ticket prices generally falling between $530 and $1390. It represents around 26% of flights on this route, featuring an in-flight duration of 19 hours and an approximate total travel time of 21 hours and 30 minutes, including layovers.
• EVA Airways: A full-service airline that also offers one-stop journeys, EVA Airways has one-way fares typically priced from $555 to $1595. This carrier accounts for about 16% of departures on this route, with a flight time of 19 hours and a total journey time of approximately 21 hours and 30 minutes, including layovers.
• Japan Airlines: Providing both one-stop and multi-stop options, Japan Airlines presents one-way fares usually ranging from $495 to $1100. It covers about 13% of departures for this route, featuring a typical 19-hour in-flight duration and a total journey time of around 21 hours and 30 minutes.
• Cathay Pacific: As a full-service airline, Cathay Pacific offers one-stop options, with one-way fares that generally range from $520 to $2895. This airline contributes to roughly 12% of departures on this route, with an in-flight time of 19 hours and a total journey time of about 21 hours and 30 minutes, including layovers.
• Korean Air: This full-service carrier specializes in one-stop flights, with one-way fares usually between $585 and $3480. Korean Air accounts for approximately 10% of departures on this route, featuring an in-flight duration of 19 hours and an estimated total travel time of 21 hours and 30 minutes, including layovers.

Travelers flying from Singapore to Chicago have the option to upgrade their flight. Leading airlines include Cathay Pacific, offering both business class and premium economy; EVA Airways, known for its premium economy service; and Delta, which provides a business class experience.

Best time to fly from Singapore (SIN) to Chicago (ORD)

The most popular months for travelers flying from Singapore to Chicago are January, March, and June, when peak temperatures in Chicago reach up to 67.3°F in June. If you prefer quieter travel, consider November, the least busy time to visit with temperatures around 42.3°F and typically the lowest average one-way fare (around $709). Flight availability peaks in June, with approximately 12 flights per week, making it easier to find convenient departure times. September and October have the fewest flights, with approximately 7 flights per week.

• Cheapest time to fly: November usually offers good deals with average one-way fare around $709, roughly 24% cheaper than the yearly average.
• Another budget-friendly time to fly: September typically offers an average one-way fare of around $733.
• Most flight options: June has the highest number of flights from Singapore to Chicago, with approximately 12 flights per week, giving you more flexibility in scheduling your trip.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

Alternative routes from Singapore (SIN) to Chicago (ORD)

• Singapore to Chicago (XSP-ORD): Seletar Airport (XSP) is located approximately 10 miles from Changi Airport (SIN), providing convenient access for travelers heading to Chicago.
• Singapore to Chicago (SIN-MDW): Midway International Airport (MDW) is situated around 16 miles from O'Hare International Airport (ORD), offering an alternative route for those flying from Singapore.
• Paya Lebar to Chicago (QPG-MDW): Paya Lebar Air Base Airport (QPG) is roughly 6 miles away from Changi Airport (SIN), with Midway International Airport (MDW) being about 16 miles from O'Hare International Airport (ORD).

How to find the best prices for flights from Singapore (SIN) to Chicago (ORD)

Getting some of the best deals on flights from Singapore to Chicago is all about timing and flexibility. Here are some key tips to help you save:

1. Best times to book and fly: cheaper fares are usually available when booking 2 to 8 weeks in advance, although most travelers tend to book at least 2 months ahead. Departures in the morning (5 a.m. to 12 p.m.) are often cheaper and are the most popular flight times, while flying on Thursday generally provides lower prices, despite Sunday being the most favored travel day.
2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Changi Airport

Chicago welcomes travelers from Singapore with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
• Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
• Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away on foot, while Rosemont Station, a train station, is about 2.2 miles from the airport and is typically reached by car.

Singapore to Chicago Flights

The cheapest times to fly from Singapore to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Singapore to Chicago are during the month of January. You can find some of the cheapest flights from Singapore to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Singapore to Chicago

Sunday is one of the best days to book for cheap flights from Singapore to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Singapore to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Singapore to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $514 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Singapore to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Singapore to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently Asked Questions

How much does a flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) cost?

You can find cheap one-way flights from $514 and cheap return flights $848 Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $637 to $5841, and return flights typically cost between $1369 and $11497. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.

*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.

What is the cheapest month to fly from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

The cheapest month to fly from SIN to ORD is January when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.

Which airlines fly direct from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

Enter SIN to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

What is the cheapest airline that flies from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

China Airlines is one of the cheapest airlines offering connecting flights from Singapore (SIN) to Chicago, IL (ORD), with round-trip tickets starting from around $1,111.43 with a layover in Taoyuan Intl. (TPE). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

*Prices based on flights available on Expedia in the last year.

How do I find cheap flights from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

To find a cheap flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

What is the best time to fly from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

What is the earliest flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from SIN to ORD. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.

What are the most popular departure times for flights from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

The most popular departure times for flights from Changi Airport (SIN) to O'Hare International Airport (ORD) are in the late evening, from 9pm to midnight. About 40% of passengers prefer this time window. Many major carriers, including United Airlines, Lufthansa, and British Airways, offer flights during this window. This timing works well because it allows you to enjoy a full day in Singapore before heading to Chicago.

How long does it take to fly from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

A flight from SIN to ORD with a layover takes around 24 hours 20 minutes, with the route covering approximately 9,352 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.

Can you fly business or first class from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

Select the "Business class" and "First class" filters when looking for SIN to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

How do I earn miles on a Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?

It's easy to earn miles on a Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

What airports do you fly into for Chicago from Changi (SIN)?

If you're planning to travel to Chicago from Changi (SIN), you can fly into O'Hare Intl. (ORD) Some flights may connect through major hubs like Narita Intl. (NRT), Incheon Intl. (ICN), San Francisco Intl. (SFO) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Is it cheaper to buy a plane ticket from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?

Typically, booking a last minute flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Is it cheaper to book a Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?

Securing a Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

Can I cancel or change the date of my flight from Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.)?

If you booked your Singapore (SIN-Changi) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.