Cheap flights from Singapore to Chicago

【Vaccinated Travel Lane (VTL)】

Singapore's newly launched Vaccinated Travel Lane (VTL) policy enables travelers from 11 countries (Brunei, Canada, Denmark, France, Germany, Italy, the Netherlands, Spain, the United Kingdom, the United States and South Korea) fly to Singapore without quarantine if they meet certain conditions. Check Singapore VTL policy to see whether you are eligible.
Please read the latestVaccinated Travel Lane (VTL) Info before traveling


Singapore to Chicago Flight price

Cheapest return ticket price

Singapore(SIN) ⇒ Chicago(ORD)

Peak season for travel


Flight Price Trends for the Coming 12 Weeks

Singapore (SIN) to Chicago (CHI)

  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11
  • 12

Cheap Flights from Singapore to Chicago

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on

Frequently Asked Questions

  • When to buy flight tickets from Singapore (SIN) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Singapore⇒Chicago based on the date and time of your booking. By analyzing data from all airlines, on, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much is a flight from Singapore (SIN) to Chicago (CHI) cost?

    According to's data, the lowest price is around S$1,848.
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • How many airports in Chicago?

  • What are some travel guidelines for Chicago during the COVID19 pandemic?

    Entry restrictions and flight schedule changes and cancellations are frequently updated and subject to change. If you plan to travel to Chicago, please obtain the most updated information from the airline you plan to book your travels with. You can also refer to COVID19 Country/Region Entry Restrictions for more information.
  • Which airlines offer free date changes for flights to this city during the COVID19 pandemic?

    There are no airlines with flights to this city that provide this service. Please use this information as a reference only and confirm with the airline prior to booking.
Flight from Singapore (SIN) to Chicago (CHI)

Chicago is among the largest and one of the most populated cities in the United States. It is a cultural hub that offers exciting attractions ranging from high-rises, parks, art galleries, museums, zoos and more. Known as the windy city, it is the birthplace of skyscrapers which is evident when you see the city’s landscape. This most relaxed city of America offers something for everyone, from amazing live shows, legendary sports events, and delicious pizza. This vibrant city which is the hub for finance, culture, education, and commerce, attracts millions of visitors every year.

Tip: You can buy the Ventra card, which is valid for trains and buses and will save your time doing cash transactions.

Getting There

There is a total of three international airports in Chicago O'Hare International Airport, Gary/Chicago International Airport & Chicago Rockford International Airport. Among these, the O'Hare International Airport is famous and also one of the busiest airports in the world. There are very few direct flights to Chicago from Singapore. There are many connecting flights from Singapore to Chicago with more than five options every day. The flight duration is more than 19 hours, depending on the layovers. The Most popular airlines to travel to Chicago from Singapore are United Airways & Etihad Airlines.

Tip: Since there are no direct flights to Chicago, make sure that you book the tickets three months in advance.

What to See 

The Windy City Chicago has much to offer for everyone making it a perfect holiday destination for the family. The city has many excellent and unique museums. Some of the Museums that you should visit are Museum of Contemporary Art, Industry, Field Museum, Chicago History Museum, American Writer’s Museum, The Art Institute of Chicago, Museum of Science and many other smaller museums. Make sure to visit Shedd Aquarium that is home to approximately more than 30 thousand animals. Visit the Skydeck at the Willis Tower, which is the tallest spot of the city to get the 360-degree view of the city. Make sure to visit Millennium Park and take a selfie with the world-famous “The Bean”. Visit Navy Pier which is full of activities where you can take the ride on Centennial Ferris Wheel or do many water-based activities including a speedboat ride.  You can learn about some of the famous landmarks on the Architecture Boat ride. Make sure that you watch a live comedy show at one of Chicago’s legendary venues, and if you are a sports lover, then you should attend one of the professional games live in one of their stadiums.  Chicago is a world-class city for cycling and Lakefront Train is a must trail for all the cyclists.

Tip: You can take the hop on hop off bus to cover some of the famous landmarks of the city.

Eat & Stay

With a population of diverse culture, Chicago has excellent choices in terms of food. To enjoy food in the budget, make sure that you visit Streetsville that has good restaurants as well as street food joints. Wicket Park has some of the most relaxed cafes and restaurant joints. If you are looking to enjoy the nightlife, then make sure that you head to River North that has some of the best clubs and bars.

Chicago has diverse options ranging from budget hotels to luxury experience. You can look in the downtown Loop for budget options and also an ideal choice if you are going there for site seeing. Hyde Park and Lincoln Park have some excellent luxury and bouquet hotels if you are visiting Chicago for a relaxing getaway.

Make sure that you visit Magnificent Mile for shopping as it is considered as the city’s elite commercial district. You will get many mid and high-end stores where you can shop from clothes to accessories.  

Tip: Make sure that you try out the signature deep dish pizza when you are in Chicago. is the best place for cheap flights from Singapore as they have fantastic offers on flight bookings. You can do Singapore to Chicago flight booking and hotel booking from here so that you can enjoy your holiday stress-free.

  • Plan Your Trip from Singapore (SIN) to Chicago (CHI)

    Chicago attracts thousands of visitors every year for both business and pleasure. Whether you’re taking a last-minute break or a much needed getaway, flights from Singapore to Chicago on can help you get there with ease. With, you can browse popular airlines with flights to Chicago, check the best season to visit, and preview Chicago attractions before you arrive. With flight deals and exciting attractions waiting for you to explore in Chicago, the best time to book flights from Singapore to Chicago is now! Planning a trip from Singapore to Chicago is easy when you use to help you make travel arrangements. Whether you are flying one-way, non-stop, or round-trip, you will find just the flight you need with us. If you want to lock in a great deal for your flights, go for a round-trip flight, if you need flexibility with your itinerary, book a one-way flight to Chicago. With, you can search for available flights and hotel rooms, and then make your booking quickly and easily online and on the go. Pack your travel accessories, make a must-see bucket list, and book your flight to Chicago on today!

  • A Trip to Remember (SIN—CHI)

    Make your journey from Singapore (SIN) to Chicago (CHI) a trip to remember by using to view Chicago attractions before you arrive. Once you know what to do in Chicago, you can reserve and book in advance for the best travel experience possible. Planning ahead is the most effective way to ensure your whole travel experience goes smoothly. Whether you need help choosing the perfect restaurant, discovering the best places to try local flavors, or finding the most stunning views in town, is with you every step of the way for your trip to Chicago.