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Cheap Flights from Singapore to Chicago

Flying from Singapore to Chicago

The distance between Singapore and Chicago is approximately 15,077.88km. According to Trip.com data, travel demand is highest in January. November is generally the cheapest month to book.

Cheapest one-way
S$ 597
Air Canada Air Canada SIN-CHI 20h 43m · 1 stop Thu, Oct 8
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Cheapest return
S$ 937
Air Canada Air Canada SIN-CHI 20h 43m · 2 stops Thu, Sep 17 - Thu, Sep 24
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Recommended airlines
Air Canada Air Canada Cheapest · From S$ 597 Eva Air Eva Air Most booked
Best time to book
February
Cheapest
January
Peak season for travel
Route details
15,077.88km
Flight distance

Explore the cheapest flights from Singapore to Chicago in the next three months. Based on Trip.com's data from the latest 7 days, one-way fares start at S$ 597, and round-trip tickets start at S$ 937.

      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Sep 17 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Thu, Sep 24 | Air Canada
        S$ 937 S$ 1,172
        20% off
        20% off
        S$ 1,172 S$ 937
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Tue, Oct 6 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Sun, Oct 11 | Air Canada
        S$ 938 S$ 1,172
        20% off
        20% off
        S$ 1,172 S$ 938
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sun, Oct 4 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Sun, Oct 11 | Air Canada
        S$ 938 S$ 1,172
        20% off
        20% off
        S$ 1,172 S$ 938
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sat, Oct 3 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Tue, Oct 6 | Air Canada
        S$ 940
        20% off
        S$ 1,172 S$ 940
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Oct 1 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Tue, Oct 6 | Air Canada
        S$ 940
        20% off
        S$ 1,172 S$ 940
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Sep 10 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Tue, Sep 15 | Air Canada
        S$ 940
        20% off
        S$ 1,172 S$ 940
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Sep 24 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Sun, Sep 27 | Air Canada
        S$ 940
        20% off
        S$ 1,172 S$ 940
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sun, Sep 20 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Thu, Sep 24 | Air Canada
        S$ 1,006
        14% off
        S$ 1,172 S$ 1,006
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sat, Oct 10 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Fri, Oct 16 | Air Canada
        S$ 1,008
        14% off
        S$ 1,172 S$ 1,008
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Tue, Sep 8 | Air Canada
        ORD 15:40
        24h 35m
        1 stop
        SIN 05:15
        Chicago - Singapore | Fri, Sep 11 | Air Canada
        S$ 1,019
        13% off
        S$ 1,172 S$ 1,019
      • SIN 13:00
        17h 25m
        1 stop
        CHI 14:00
        Singapore - Chicago | Fri, Aug 14 | Normal Airline
        CHI 15:00
        6h
        Direct
        SIN 16:00
        Chicago - Singapore | Sun, Aug 16 | Normal Airline
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      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Oct 8 | Air Canada
        S$ 597 S$ 689
        13% off
        13% off
        S$ 689 S$ 597
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Sep 10 | Air Canada
        S$ 599 S$ 689
        13% off
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sat, Oct 3 | Air Canada
        S$ 599 S$ 689
        13% off
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Oct 1 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Thu, Sep 17 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sun, Sep 13 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sat, Sep 12 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Tue, Sep 29 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sun, Sep 27 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 07:00
        20h 43m
        1 stop
        ORD 14:43
        Singapore - Chicago | Sat, Sep 26 | Air Canada
        S$ 599
        13% off
        S$ 689 S$ 599
      • SIN 13:00
        17h 25m
        1 stop
        CHI 14:00
        Singapore - Chicago | Fri, Aug 14 | Normal Airline
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Popular airlines from Singapore to Chicago

You can choose from 10 airlines that fly from Singapore to Chicago, including Eva Air, United Airlines, and Japan Airlines. Air Canada offers the lowest prices on this route.
Eva Air logo Eva Air
United Airlines logo United Airlines
Japan Airlines logo Japan Airlines
All Nippon Airways logo All Nippon Airways
Air Canada logo Air Canada
Qatar Airways logo Qatar Airways
Korean Air logo Korean Air
Turkish Airlines logo Turkish Airlines
Delta Air Lines logo Delta Air Lines
Cathay Pacific logo Cathay Pacific
Airlines are determined based on actual purchased flight tickets from Singapore to Chicago according to previous 12 months data from Trip.com.

Trip.com Price Insights on Flights from Singapore to Chicago.

What is the cheapest month for one-way flights from Singapore to Chicago?

The average price of one-way flights from Singapore to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from Singapore to Chicago is February, with an average price of S$ 861, and the most expensive month is March, with an average price of up to S$ 1,436.

S$ 1,436
S$ 1,149
S$ 861
S$ 574
    Cheapest
  • S$ 1,048
    Aug
  • S$ 1,098
    Sep
  • S$ 977
    Oct
  • S$ 1,031
    Nov
  • S$ 915
    Dec
  • S$ 1,270
    Jan
  • S$ 861
    Feb
  • S$ 1,436
    Mar
  • S$ 1,315
    Apr
  • S$ 1,100
    May
  • S$ 1,072
    Jun
  • S$ 1,136
    Jul

What is the cheapest month for round-trip flights from Singapore to Chicago?

The average price of round-trip flights from Singapore to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for round-trip flights from Singapore to Chicago is April, with an average price of S$ 1,266, and the most expensive month is August, with an average price of up to S$ 2,350.

S$ 2,350
S$ 1,808
S$ 1,266
S$ 724
    Cheapest
  • S$ 2,350
    Aug
  • S$ 1,811
    Sep
  • S$ 1,527
    Oct
  • S$ 1,840
    Nov
  • S$ 2,345
    Dec
  • S$ 1,974
    Jan
  • S$ 1,831
    Feb
  • S$ 2,024
    Mar
  • S$ 1,266
    Apr
  • S$ 1,981
    May
  • S$ 2,238
    Jun
  • S$ 1,945
    Jul

Frequently Asked Questions

  • Which airlines offer the cheapest flights from Singapore (SIN) to Chicago (CHI)?

    Based on Trip.com data, Air Canada offers one-way fares as low as S$ 597 on Cheapest nonstop routes (e.g. SIN to ORD on Thu, Oct 8), while Air Canada offers Cheapest nonstop round-trips from S$ 937 departing on Thu, Sep 17 and returning on Thu, Sep 24.
  • At the moment, you can catch a direct flight from Singapore to Chicago with the following airlines, including: American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Singapore to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Singapore to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Oct 8, with one-way flights priced at just S$ 597.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Air Canada.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around January.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Singapore to Chicago is November, when demand for travel is lower.
  • After crunching the numbers on our August flight calendar, it's currently cheapest to fly from Singapore to Chicago on August 27, 2026 with All Nippon Airways, with prices starting at S$ 1,106.
  • You can land at any one of the following hubs in Chicago, with Singapore Changi Airport to O'Hare International Airport (SIN-ORD) is by far the most common option on this route: O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Singapore is 14h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
  • Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Singapore to Chicago is S$ 1,526. Fares vary by travel date, airline and availability.
  • Enter Singapore and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveller details and complete payment to receive your confirmation.

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.

Trip.com 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.

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Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.