Cheap Flights from Chicago to Singapore

Compare Chicago to Singapore flight deals

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

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Flight deals from Chicago to Singapore

Looking for a cheap last-minute deal or the best return flight from Chicago to Singapore? If you want to travel next month, return fares start from ج.م.‏ 61,959. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago to Singapore

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

Alternative Chicago to Singapore routes

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

Chicago to Singapore: Flight information

The things to know before you go.
Cheapest flight foundج.م.‏ 23,218
Cheapest month to flyApril

Finding cheap flights from Chicago to Singapore: Frequently asked questions

There are 2 airports in Singapore: Seletar and Singapore Changi.
The best price we found for a return flight from Chicago to Singapore is ج.م.‏ 53,436. 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 Chicago to Singapore. But we found flights with one or more stops from ج.م.‏ 53,436.
As of April 2026, there are no flights flying from Chicago to Singapore.
The cheapest month to fly from Chicago to Singapore is usually September.
If you're flying from Chicago, the cheapest airport near Singapore is Singapore Changi – which is 17.9 km away from the centre of Singapore. We've found flights into this airport from ج.م.‏ 53,436.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Singapore on Monday, 21 September 2026.
No airlines currently offer direct flights between Chicago and Singapore. 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 Singapore 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 Singapore is around 40 days in advance, so don’t leave your flight to the last minute.
In April, the average temperature is usually around 28°C. May is typically the warmest month in Singapore, when it usually averages around 30°C. You can expect the least rain in February. The coldest month is December, with temperatures averaging 25°C. The rainiest month is December.
The cheapest airline that flies to Singapore is Air Canada .

Flying from Chicago to Singapore: what you need to know

  • Get your holiday planning started by considering where you'll board your flight from Chicago to Singapore. O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.

  • When planning your arrival in Singapore, Changi International Airport (SIN) and Seletar Airport (XSP) are the primary gateways.

  • The timezone in Singapore is UTC+8, which is 13 hours ahead of Chicago.

  • Give yourself plenty of time to make your Chicago to Singapore flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Be prepared for longer lines during popular months like August. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a wise move.

How to find the cheapest flights from Chicago to Singapore

  • Don't leave everything to the last moment. You're more likely to find cheap Chicago to Singapore flights if you book early. Airlines often have some great early bird discounts.

  • The 'Whole month' tool will show you the cheapest plane tickets from Chicago to Singapore throughout the entire month. It's an easy way to find a bargain if your travel plans are flexible.

  • There's no need to check back in every day to see if fares have dropped when you set up a Price Alert. We'll let you know as soon as there's a better deal on cheap flights from Chicago to Singapore.

  • Save money on your Chicago to Singapore flight with the help of our filters. Choose your preferred duration, number of stops and airlines, then sort the results by 'Cheapest' to see the best deals.

Flying from Chicago

O'Hare International Airport (ORD)

  • A stopover is the perfect opportunity to take a travel break — and possibly even explore a different city. When browsing Chicago to Singapore flights leaving from O'Hare International Airport, uncheck the 'Direct flights only' box to see where you can stop along the way. Top options include:

    • Shanghai Pudong International Airport (PVG)

    • London Heathrow Airport (LHR)

    • Haneda Airport (HND)

  • The journey from central Chicago to ORD takes about 55 minutes by public transport. If you ride-share, drive or take a cab, you'll cover the 26 kilometres in 35 minutes or so, depending on traffic.

  • Want a hassle-free start to your holiday? Stay near O'Hare International Airport. Whether you're catching an early flight from Chicago to Singapore or just don't want to be rushed, these hotels are ideal:

  • When it comes to the on-time performance of O'Hare International Airport, 74.85% of flights stick to their scheduled arrival time.

  • ORD's address is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Visit family or friends or just take some time to unwind with a stopover. If you'd like to split up your Chicago to Singapore flight, check out these options when departing from Chicago Midway International Airport:

    • Los Angeles International Airport (LAX)

    • Seattle-Tacoma International Airport (SEA)

    • San Francisco International Airport (SFO)

  • You can reach MDW from central Chicago in about 20 minutes by car, depending on traffic. The ride on public transport takes roughly 45 minutes to cover the 14 kilometres or so.

  • Want to treat yourself to an extra night away before boarding your flight from Chicago to Singapore? Relax in a hotel near Chicago Midway International Airport before your adventure officially starts. Stay at one of these accommodation options:

  • Chicago Midway International Airport has an on-time performance rate of 78%. This figure provides insight into how often flights that leave from this airport land on schedule.

  • You'll find MDW at 5700 South Cicero.

Arriving in Singapore

Changi International Airport (SIN)

  • The distance from Changi International Airport (SIN) to central Singapore is roughly 18 kilometres. It takes about 20 minutes to get to the centre driving.

  • If you're taking public transport, expect a journey time of around 1 hour.

  • If you have a late flight from Chicago to Singapore, nothing beats the convenience of staying close to the terminal. Grab your suitcases from the carousel and then be showered and relaxing not long after at one of these hotels near SIN:

  • Go wherever you want, whenever you want with a Changi International Airport rental car. Book your wheels from Avis, Sixt or Green Motion and chase adventure across Singapore and beyond.

  • For the best deal, reserve your ride from Changi International Airport about two weeks ahead of your Chicago to Singapore flight.

Seletar Airport (XSP)

  • Seletar Airport (XSP) is about 14 kilometres from central Singapore. After your flight from Chicago to Singapore, it'll take you approximately 25 minutes to get to the heart of the city in a cab or ride-share.

  • Travelling by public transport will take around 1 hour 25 minutes.

  • After your flight from Chicago to Singapore, tuck yourself in at a hotel close to XSP. These are some great options that'll help you slip into relaxation mode:

Best time to go to Singapore

  • It's time to choose your dates for your flight from Chicago to Singapore. April is the busiest month to visit Singapore. If you want a more relaxed atmosphere, go in February.

  • Book a Chicago to Singapore ticket departing in May if you're eager to visit the city during its warmest month. Expect temperatures in Singapore to range from 25ºC to 31ºC.

  • If you want cooler conditions, look for a cheap flight from Chicago to Singapore in January when temperatures average between 24ºC and 30ºC.

More about Singapore

  • Start your Singapore trip off on the right foot by choosing the ideal place to stay. After booking your flight from Chicago to Singapore, browse our range of accommodation options including:

  • Marina Bay Sands and Gardens by the Bay are a couple of popular attractions to put on your Singapore itinerary. Keep the momentum going by heading to Universal Studios Singapore.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.