S$ 677+ 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 16-3. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
23 Feb — 2 Mar1
1 adult
1 adult, Economy, 0 bags

Flights to Chicago in 2026

Enter your travel dates to find the best prices.

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 24 January 2026.

Tue 17-222:20
SIN
-
ORD
1 stop21h 59m
United Airlines
Wed 18-209:01
ORD
-
SIN
1 stop32h 59m
United Airlines
Deal found 21-1S$ 1,194
Sat 24-110:10
SIN
-
ORD
1 stop20h 47m
United Airlines
Sat 24-119:58
ORD
-
SIN
1 stop34h 17m
United Airlines
Deal found 23-1S$ 1,195
Sun 22-222:20
SIN
-
ORD
1 stop21h 59m
United Airlines
Thu 26-206:25
ORD
-
SIN
1 stop23h 50m
United Airlines
Deal found 22-1S$ 1,199
Fri 27-322:20
SIN
-
ORD
1 stop20h 59m
United Airlines
Mon 20-406:25
ORD
-
SIN
1 stop23h 10m
United Airlines
Deal found 22-1S$ 1,202
Fri 6-210:10
SIN
-
ORD
1 stop25h 22m
United Airlines
Mon 9-217:16
ORD
-
SIN
1 stop24h 44m
United Airlines
Deal found 23-1S$ 1,203
Sun 25-110:10
SIN
-
ORD
1 stop20h 47m
Lufthansa
Sat 7-218:29
ORD
-
SIN
1 stop35h 46m
Lufthansa
Deal found 23-1S$ 1,212
Mon 9-310:40
SIN
-
MDW
2 stops36h 16m
Delta
Mon 16-318:34
MDW
-
SIN
2 stops40h 36m
Delta
Deal found 23-1S$ 1,220
Sun 1-208:15
SIN
-
ORD
1 stop19h 30m
Japan Airlines
Wed 4-210:35
ORD
-
SIN
1 stop24h 15m
Japan Airlines
Deal found 23-1S$ 1,220
Mon 2-308:15
SIN
-
ORD
1 stop19h 30m
Japan Airlines
Wed 4-319:42
ORD
-
SIN
2 stops39h 08m
Japan Airlines
Deal found 23-1S$ 1,243
Mon 2-322:30
SIN
-
MDW
2 stops28h 16m
Delta
Wed 4-318:40
MDW
-
SIN
2 stops39h 30m
Delta
Deal found 23-1S$ 1,415
Mon 8-613:45
SIN
-
MDW
2 stops28h 15m
Multiple Airlines
Thu 6-817:55
MDW
-
SIN
2 stops29h 40m
Multiple Airlines
Deal found 24-1S$ 1,419
Fri 26-613:45
SIN
-
MDW
2 stops29h 10m
Multiple Airlines
Mon 20-717:15
MDW
-
SIN
2 stops30h 20m
Multiple Airlines
Deal found 23-1S$ 1,429

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 200,618 searches and data was last updated on 24 January 2026.

Return from

S$ 1,194

One-way from

S$ 677

Popular in

January

Cheapest in

September

Average price

S$ 2,019
United Airlines
  • United Airlines
  • 17-2-18-2
  • 2 total stops
  • 54h 58m total
  • Singapore to Chicago
8-3
  • 8-3
  • 2 total stops
  • 48h 20m total
  • Singapore to Chicago
Highest demand for flights based on searches. 10% potential increase in price (S$ 165 potential increase over avg. return price).
Cheapest flight prices on average. 4% potential price decrease (S$ 58 potential savings vs. average return price).
Average for return flights in January 2026

Cheapflights Fare Finder

 
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 24 January 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Singapore

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 21-3

22:20-06:19

1 stop20h 59m

Chicago O'Hare Intl

Sat 28-3

14:26-18:35

1 stop39h 09m

S$ 1,202

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-2

10:10-05:44

1 stop33h 34m

Chicago O'Hare Intl

Fri 20-2

06:25-20:15

1 stop23h 50m

S$ 1,203

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9-3

10:10-18:52

1 stop21h 42m

Chicago O'Hare Intl

Mon 16-3

18:20-07:00

1 stop23h 40m

S$ 1,203

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 6-2

10:10-21:32

1 stop25h 22m

Chicago O'Hare Intl

Mon 9-2

17:16-08:00

1 stop24h 44m

S$ 1,203

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 2-3

10:10-18:41

1 stop22h 31m

Chicago O'Hare Intl

Wed 4-3

14:35-08:00

1 stop27h 25m

S$ 1,203

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 17-2

22:20-06:19

1 stop21h 59m

Chicago O'Hare Intl

Wed 18-2

14:35-08:00

1 stop27h 25m

S$ 1,208

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Wed 11-3

10:40-22:31

2 stops24h 51m

Chicago Midway

Tue 17-3

09:35-05:00

2 stops30h 25m

S$ 1,220

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 9-3

10:40-09:56

2 stops36h 16m

Chicago Midway

Mon 16-3

18:34-00:10

2 stops40h 36m

S$ 1,220

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9-3

22:30-23:54

2 stops38h 24m

Chicago O'Hare Intl

Mon 16-3

17:59-00:10

2 stops41h 11m

S$ 1,220

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 11-3

11:15-08:35

2 stops34h 20m

Chicago O'Hare Intl

Tue 17-3

14:10-14:10

3 stops35h 00m

S$ 1,344

Flights are sorted by cheapest return flights first.

Deals found on 22-1

Showing 1-10 of 38 results
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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.
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

How long is the flight to Chicago?

On average, a flight from Singapore to Chicago takes 24 hours 35 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 cheapest airlines that fly to Chicago?

The cheapest airlines flying from Singapore to Chicago are United Airlines, Japan Airlines and ANA.

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 24 January 2026.
See what other customers who have flown with EVA Air, ANA, andCathay Pacific 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.

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.6

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.6

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.
8.4
Very Good

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.6

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.6

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.

Overall

8.4

Comfort

8.3

Food

8.1

Crew

8.6

Boarding

8.4

Entertainment

8.0

Reviews

1 / 20
6.0
Good

Hannah,Jan 2026

TPE - SFO

I like the flight attendants the most. The are very helpful.

FAQs about flying to Chicago

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.
  • 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.

  • What is the best airline to fly to Chicago?

    Based on reviews from Cheapflights users, United Airlines is rated the highest out of the airlines that fly to Chicago.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Singapore Changi offers the quickest one-way flight (21 hours 5 minutes).

  • Does Chicago O'Hare Intl have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl?

    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).

See more FAQs

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Airports serving Chicago

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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.

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