This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9-11. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
29 Nov — 6 Dec1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Flights to Chicago in 2026
Enter your travel dates to find the best prices.
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Best
Last-minute
One-way
Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 30 October 2026.
Thu 12-1108:40 -
1 stop19h 57m
Wed 25-1115:30 -
1 stop25h 30m
Deal found 25-10S$ 1,010
Thu 12-1108:40 -
1 stop19h 57m
Sun 15-1108:45 -
2 stops32h 10m
Deal found 29-10S$ 1,040
Thu 19-1108:40 -
1 stop19h 57m
Mon 23-1116:45 -
2 stops48h 15m
Deal found 25-10S$ 1,058
Mon 9-1123:10 -
2 stops34h 49m
Tue 24-1108:45 -
2 stops32h 10m
Deal found 26-10S$ 1,076
Sun 22-1108:15 -
1 stop37h 15m
Sun 29-1113:30 -
1 stop27h 10m
Deal found 25-10S$ 1,087
Tue 27-1002:20 -
1 stop21h 40m
Wed 4-1106:29 -
2 stops34h 11m
Deal found 27-10S$ 1,108
Best flights to Chicago
Discover carefully curated flight deals to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 30 October 2026.
Sun 22-1110:30 -
1 stop36h 00m
Sun 29-1106:49 -
2 stops32h 11m
Deal found 25-10S$ 1,222
Tue 22-1203:15 -
2 stops30h 10m
Sun 3-118:50 -
1 stop36h 25m
Deal found 28-10S$ 1,704
Tue 15-1210:10 -
1 stop24h 30m
Sun 3-106:00 -
1 stop36h 00m
Deal found 27-10S$ 1,870
Thu 24-1210:30 -
1 stop36h 00m
Sat 2-114:27 -
2 stops39h 58m
Deal found 28-10S$ 1,515
Wed 23-1203:15 -
1 stop25h 15m
Sun 3-118:50 -
1 stop36h 25m
Deal found 29-10S$ 1,890
Wed 23-1222:30 -
2 stops39h 29m
Sun 3-117:45 -
2 stops40h 30m
Deal found 28-10S$ 1,759
Wed 16-1220:15 -
1 stop32h 15m
Sun 3-118:50 -
1 stop36h 25m
Deal found 25-10S$ 1,894
Tue 22-1210:30 -
2 stops27h 29m
Sun 3-106:00 -
2 stops28h 15m
Deal found 25-10S$ 1,791
Sun 13-1203:15 -
1 stop25h 15m
Sun 3-118:50 -
1 stop36h 25m
Deal found 25-10S$ 1,894
Fri 25-1222:30 -
1 stop24h 00m
Sat 2-114:27 -
2 stops39h 58m
Deal found 29-10S$ 1,821
Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 30 October 2026 and is based on user searches.
Fri 30-1008:15 -
2 stops28h 15m
Thu 5-1113:30 -
1 stop37h 55m
Deal found 28-10S$ 1,117
Mon 9-1123:10 -
2 stops34h 49m
Tue 24-1108:45 -
2 stops32h 10m
Deal found 26-10S$ 1,076
Thu 12-1108:40 -
1 stop19h 57m
Wed 25-1115:30 -
1 stop25h 30m
Deal found 25-10S$ 1,010
Thu 12-1108:40 -
1 stop19h 57m
Sun 15-1108:45 -
2 stops32h 10m
Deal found 29-10S$ 1,040
Thu 19-1108:40 -
1 stop19h 57m
Mon 23-1116:45 -
2 stops48h 15m
Deal found 25-10S$ 1,058
Sun 22-1108:15 -
1 stop37h 15m
Sun 29-1113:30 -
1 stop27h 10m
Deal found 25-10S$ 1,087
One-way flights to Chicago
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 30 October 2026.
Mon 9-1119:25 -
1 stop26h 10m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 26-10S$ 625
Tue 3-1119:25 -
1 stop26h 10m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 28-10S$ 626
Thu 19-1108:40 -
1 stop19h 57m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 25-10S$ 635
Thu 12-1108:40 -
1 stop19h 57m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 25-10S$ 640
Fri 13-1108:40 -
2 stops35h 18m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 25-10S$ 644
Sun 8-1108:40 -
1 stop19h 57m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 29-10S$ 657
Tue 10-1108:40 -
1 stop25h 19m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 25-10S$ 663
Tue 15-1208:40 -
2 stops37h 20m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 29-10S$ 665
Find flight deals to Chicago
Find the latest flights to Chicago in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 7,457,451 searches and data was last updated on 30 October 2026.
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 7,457,451 searches and data was last updated on 30 October 2026.
Use the filters below to find and compare flights to Chicago that are best for you.
Fly from
Route
Depart
Return
Price
Cheapest return flight
Fastest return journey
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Thu 25-3
22:30-09:30
1 stop24h 00m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 724
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Fri 19-3
10:30-09:30
1 stop36h 00m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 724
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Sat 16-1
22:30-23:58
2 stops39h 28m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 727
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Tue 9-3
10:30-22:20
2 stops25h 50m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 729
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Fri 29-1
01:40-23:59
2 stops36h 19m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 730
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Wed 18-11
08:15-07:30
1 stop37h 15m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 747
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Wed 18-11
08:55-00:21
2 stops29h 26m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 767
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Thu 18-3
01:40-23:46
2 stops35h 06m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 798
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Mon 16-11
22:30-17:05
2 stops32h 35m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 798
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Thu 10-12
01:40-23:59
2 stops36h 19m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 802
Flights are sorted by cheapest return flights first.
Deals found on 28-10
Showing 1-10 of 22 resultsSorted by cheapest first
1
2
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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.
SIN-CHI
SIN-ORD
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight to Chicago
SIN-CHI
SIN-ORD
How long is the flight to Chicago?
On average, a flight from Singapore to Chicago takes 23 hours 32 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 United Airlines and EVA Air.
What are the cheapest airlines that fly to Chicago?
The cheapest airlines flying from Singapore to Chicago are United Airlines and EVA Air.
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 30 October 2026.
See what other customers who have flown with EVA Air,Korean Air, andJapan Airlines to the United States have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
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.
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.
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 $200 million worth of property. From this disaster came the opportunity to plan and rebuild the entire city.
Chicago is also home to the nine time world-championship football team, the Chicago Bears and Wrigley Field, the second-oldest ballpark in the Major League baseball, built in 1914, just behind Boston’s Fenway Park, built in 1912.
When is the best time to fly to Chicago?
Peak season:
Summer is the peak of the festival season in the Chicago area with major events taking place in the parks and neighbourhoods every weekend, in spite of the heat and humidity from the Lake. September can be the most enjoyable and mild month of the year but there’s less going on during this period.
Off season:
January to March is when Chicago is least busy and deals on hotels andcheap flights to Chicagoare usually attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.
Can I find cheaper flights to Chicago if I am willing to have stopovers?
Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.
Based on reviews from Cheapflights users, EVA Air is rated the highest out of the airlines that fly to Chicago.
What is the cheapest airport to fly to in Chicago?
Chicago O'Hare Intl is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost S$ 222, while return flights cost around S$ 467.
Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights to Chicago?
Deals for Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.
Why should you use Cheapflights to find cheap flight tickets to Chicago?
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights to Chicago for you. Better yet — we are completely free to use.
Can Cheapflights find flights to Chicago with no change fees?
Yes! Cheapflights helps users easily find flights to Chicago with no change fees.
Can Cheapflights notify me if prices for flights to Chicago become cheaper?
Of course! You can track prices for flights to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals to set up your price alerts.
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