S$ 653+ Cheap flights to Chicago
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 31-3. Fares are subject to change and may not be available on all flights or dates of travel.
Flights to Chicago in 2025
Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 200,618 searches and data was last updated on 28 February 2025.
Return from | S$ 1,080 |
---|---|
One-way from | S$ 653 |
Popular in | August |
Cheapest in | February |
Average price | S$ 1,452 |
Find flight deals to Chicago
Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 28 February 2025.
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 28 February 2025.
Find flights to Chicago within your budget
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 200,618 searches and data was last updated on 28 February 2025.
Fly from
Route
Depart
Return
Price
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sun 13-4
20:40-11:36
1 stop27h 56m
Chicago O'Hare Intl
Sun 20-4
12:45-06:45
1 stop29h 00m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sat 12-4
01:50-14:25
1 stop25h 35m
Chicago O'Hare Intl
Sun 20-4
16:00-05:30
1 stop24h 30m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sun 13-4
07:30-09:40
1 stop39h 10m
Chicago O'Hare Intl
Sun 20-4
12:20-19:55
1 stop42h 35m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Tue 24-6
09:10-09:40
1 stop37h 30m
Chicago O'Hare Intl
Wed 23-7
11:25-07:30
1 stop31h 05m
SingaporeChicago
SIN - MDW
SINMDW
Singapore Changi
Wed 2-4
22:30-12:35
2 stops27h 05m
Chicago Midway
Thu 10-4
10:25-05:00
2 stops29h 35m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sun 13-4
15:15-05:45
2 stops27h 30m
Chicago O'Hare Intl
Sun 20-4
16:55-13:50
2 stops31h 55m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sun 13-4
07:30-09:40
1 stop39h 10m
Chicago O'Hare Intl
Sun 20-4
07:50-05:00
2 stops32h 10m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Sun 13-4
09:10-12:31
1 stop40h 21m
Chicago O'Hare Intl
Sun 20-4
11:30-07:05
2 stops30h 35m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Fri 18-7
09:00-07:25
1 stop35h 25m
Chicago O'Hare Intl
Mon 28-7
12:00-19:05
1 stop42h 05m
SingaporeChicago
SIN - ORD
SINORD
Singapore Changi
Fri 9-5
19:45-17:55
2 stops35h 10m
Chicago O'Hare Intl
Wed 14-5
11:25-17:45
2 stops41h 20m
Best time to book a flight to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Travel insights for flights to Chicago
Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.
When is the best time to book a flight to Chicago?
Use this chart to determine the optimal time to book a return flight from Singapore to Chicago. Price data was last updated on 25 February 2025.
To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
How long is the flight to Chicago?
On average, a flight from Singapore to Chicago takes 26 hours 19 minutes. Flights to Chicago from other popular cities in Singapore will vary in length. Below are a few examples of popular routes and their flight times.
What are the most popular airlines that fly to Chicago?
The most popular airlines flying from Singapore to Chicago are EVA Air, United Airlines and Japan Airlines.
What are the cheapest airlines that fly to Chicago?
The cheapest airlines flying from Singapore to Chicago are Turkish Airlines, United Airlines and Cathay Pacific.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 28 February 2025.
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
Piotr,Feb 2025
TPE - ORD
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
Piotr,Feb 2025
TPE - ORD
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
Piotr,Feb 2025
TPE - ORD
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
Piotr,Feb 2025
TPE - ORD
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
Piotr,Feb 2025
TPE - ORD
Crew
Entertainment
Overall
Boarding
Food
Comfort
Reviews
Piotr,Feb 2025
TPE - ORD
Chicago climate
Chicago has an extreme climate with very hot summers and bitterly cold winters, its lakeside setting only slightly moderating the temperatures and adding some humidity to the atmosphere. Chicago has distinct seasons, with a short spring, when temperatures are moderate and nights frosty. Summers are hot, sunny and humid, from June to the end of September, with cool evenings when breezes blow in from Lake Michigan. Autumn is a lovely time of year when the air is crisp and cool, with blue skies and sunshine. Winters in Chicago are icy and prone to cold, harsh winds. Snow is common, and it is also very rainy during the winter months.
Getting around Chicago
No need to worry about getting around Chicago. There are plenty of ways to get around. Hop on the El, short for elevated train, the city’s subway system, or one of the buses that runs all over the city. For information about fares and routes, check out the website for the Chicago Transit Authority. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Biking is becoming increasingly popular around the city, thanks to the city’s former mayor encouraging residents to ride their bikes as a mode of transportation. With all of Chicago’s lakefront property, biking can be a great way to enjoy the city.
What is good to know if travelling to Chicago?- Any shopping in Chicago has to begin on State Street, in the centre of the Loop. The Marshall Field’s flagship department store opened in 1852 there. Check out the famed “Magnificent Mile” along Michigan Avenue from the Chicago River to Oak Street for specialty shops and boutiques with designers from Paris, Milan and Manhattan blending with Chicago’s Gold Coast style.
- The Chicago Cultural Centre houses one of the city’s official Visitor Information Centres and offers more than 600 free art programmes annually.
- Along the shores of Lake Michigan, you’ll find Chicago’s cultural delights including the Art Institute of Chicago, the Goodman Theatre, the Lyric Opera at the Civic Opera House building, and the Chicago Symphony Orchestra.
- Chicago’s lakefront is almost exclusively recreational park area from north to south, and features Grant Park, the home of Buckingham Fountain, the Petrillo Bandshell, the Grant Park Symphony (where free concerts are presented throughout the summer), and Chicago’s annual two-week food orgy, the Taste of Chicago, where more than three million people “chow down”.
- The beauty of Chicago springs from the tragedy of the Great Chicago Fire in 1871 that claimed 300 lives, left 90,000 Chicagoans homeless and destroyed $200 million worth of property. From this disaster came the opportunity to plan and rebuild the entire city.
- Chicago is also home to the nine time world-championship football team, the Chicago Bears and Wrigley Field, the second-oldest ballpark in the Major League baseball, built in 1914, just behind Boston’s Fenway Park, built in 1912.
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Airports serving Chicago
Book a flight to or from one of these Chicago airports.
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