This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 19-11. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
4 Dec — 11 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.
Cheapest
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 4 November 2026.
Thu 12-1108:40 -
1 stop25h 19m
Wed 25-1107:05 -
2 stops27h 40m
Deal found 3-11S$ 1,068
Wed 4-1102:20 -
1 stop21h 40m
Sun 8-1113:30 -
1 stop27h 10m
Deal found 31-10S$ 1,072
Tue 24-1110:30 -
2 stops25h 03m
Tue 8-1206:40 -
2 stops32h 20m
Deal found 2-11S$ 1,089
Tue 17-1106:35 -
2 stops27h 17m
Mon 23-1115:50 -
2 stops49h 10m
Deal found 4-11S$ 1,144
Tue 22-1208:15 -
1 stop39h 45m
Tue 5-109:33 -
2 stops49h 17m
Deal found 31-10S$ 1,165
Sat 26-1208:40 -
1 stop19h 57m
Thu 7-115:35 -
1 stop25h 25m
Deal found 2-11S$ 1,196
Tue 22-1208:40 -
2 stops29h 50m
Thu 7-115:35 -
1 stop25h 25m
Deal found 2-11S$ 1,204
Sat 26-1208:40 -
1 stop19h 57m
Wed 6-115:45 -
2 stops49h 15m
Deal found 2-11S$ 1,206
Tue 22-1208:40 -
2 stops29h 50m
Wed 6-115:45 -
2 stops49h 15m
Deal found 2-11S$ 1,214
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 4 November 2026.
Tue 1-1210:30 -
1 stop36h 00m
Tue 8-1206:40 -
2 stops32h 20m
Deal found 3-11S$ 1,366
Sun 20-1219:25 -
1 stop26h 10m
Mon 4-113:15 -
1 stop30h 20m
Deal found 31-10S$ 1,468
Tue 22-1208:40 -
2 stops25h 18m
Sun 3-115:30 -
1 stop25h 30m
Deal found 30-10S$ 1,737
Thu 12-1120:45 -
1 stop34h 10m
Fri 11-1222:45 -
1 stop24h 25m
Deal found 3-11S$ 1,954
Wed 23-1221:20 -
2 stops31h 50m
Thu 7-119:45 -
2 stops34h 35m
Deal found 31-10S$ 1,959
Sun 20-1219:25 -
1 stop26h 10m
Thu 7-113:15 -
1 stop30h 20m
Deal found 2-11S$ 1,514
Wed 23-1219:25 -
2 stops37h 33m
Wed 6-113:15 -
1 stop30h 20m
Deal found 31-10S$ 1,593
Fri 25-1210:30 -
2 stops27h 29m
Thu 31-1206:00 -
2 stops33h 00m
Deal found 4-11S$ 1,790
Sun 20-1219:25 -
2 stops37h 33m
Wed 6-113:15 -
1 stop30h 20m
Deal found 2-11S$ 1,596
Thu 24-1222:30 -
1 stop24h 00m
Tue 29-1206:00 -
2 stops28h 15m
Deal found 4-11S$ 1,932
Tue 22-1219:25 -
1 stop26h 10m
Sat 2-113:15 -
1 stop30h 20m
Deal found 31-10S$ 1,930
Wed 23-1219:25 -
1 stop26h 10m
Sun 3-113:15 -
1 stop30h 20m
Deal found 1-11S$ 1,964
Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 4 November 2026 and is based on user searches.
Wed 4-1102:20 -
1 stop21h 40m
Sun 8-1113:30 -
1 stop27h 10m
Deal found 31-10S$ 1,072
Thu 12-1108:40 -
1 stop25h 19m
Wed 25-1107:05 -
2 stops27h 40m
Deal found 3-11S$ 1,068
Tue 17-1106:35 -
2 stops27h 17m
Mon 23-1115:50 -
2 stops49h 10m
Deal found 4-11S$ 1,144
Tue 24-1110:30 -
2 stops25h 03m
Tue 8-1206:40 -
2 stops32h 20m
Deal found 2-11S$ 1,089
Tue 22-1208:15 -
1 stop39h 45m
Tue 5-109:33 -
2 stops49h 17m
Deal found 31-10S$ 1,165
Tue 22-1208:40 -
2 stops29h 50m
Thu 7-115:35 -
1 stop25h 25m
Deal found 2-11S$ 1,204
Tue 22-1208:40 -
2 stops29h 50m
Wed 6-115:45 -
2 stops49h 15m
Deal found 2-11S$ 1,214
Sat 26-1208:40 -
1 stop19h 57m
Thu 7-115:35 -
1 stop25h 25m
Deal found 2-11S$ 1,196
Sat 26-1208:40 -
1 stop19h 57m
Wed 6-115:45 -
2 stops49h 15m
Deal found 2-11S$ 1,206
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 4 November 2026.
Thu 19-1108:40 -
1 stop19h 57m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 3-11S$ 631
Wed 27-106:35 -
2 stops27h 23m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 2-11S$ 661
Sat 6-220:20 -
2 stops32h 12m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 1-11S$ 679
Tue 24-1106:35 -
2 stops27h 17m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 3-11S$ 680
Fri 20-1108:40 -
2 stops38h 22m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 3-11S$ 684
Mon 18-122:20 -
2 stops35h 38m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 1-11S$ 685
Thu 21-106:35 -
2 stops28h 05m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 1-11S$ 697
Mon 18-122:25 -
1 stop25h 35m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 31-10S$ 699
Wed 27-122:30 -
1 stop24h 00m
Wed 31-1200:00 -
Nonstop0h 00m
Deal found 2-11S$ 707
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 4 November 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 4 November 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
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Sun 22-11
22:30-20:17
2 stops35h 47m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 721
Fastest return journey
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Mon 23-11
01:40-08:30
1 stop20h 50m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 721
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$ 722
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Fri 29-1
01:40-08:30
1 stop20h 50m
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
Sun 17-1
22:30-23:59
2 stops39h 29m
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
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
Tue 19-1
02:20-10:00
1 stop21h 40m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 731
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Thu 21-1
22:25-10:00
1 stop25h 35m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 731
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Sun 28-2
02:20-10:00
1 stop21h 40m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 733
SingaporeChicago
SIN Singapore Changi - ORD Chicago O'Hare Intl
SINORD
Singapore Changi
Fri 15-1
08:15-07:30
1 stop37h 15m
Chicago O'Hare Intl
Wed 31-12
00:00-13:30
Nonstop0h 00m
S$ 744
Flights are sorted by cheapest return flights first.
Deals found on 4-11
Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3
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 24 hours 58 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 4 November 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.
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book With Flexibility
Our users can plan ahead with confidence and find flights with no change fees.
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
We value your privacy
Cheapflights and its partners wish to use cookies or similar technologies to store and/or access information on and about your device and process personal data such as your IP address, device identifiers etc., in order to improve your experience on the site, to analyse navigation, to offer and measure personalised advertising, and to facilitate sharing on social networks. We also allow the use of third-party cookies (including those from our advertising partners) on our sites.
By clicking 'Accept', you consent to your data being processed by 0 vendors on this web site for the purposes described in this notice. You can review the vendors and their individual processing purposes on the .
To review individual processing purposes and cookie categories, please click ’Select individual purposes’. You can review your choices and withdraw your consent at any time by clicking the ’Privacy Preferences’ link in the page side navigation.