S$ 607+ 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 9-10. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Return from

S$ 1,051

One-way from

S$ 607

Popular in

January

Cheapest in

October

Average price

S$ 1,247
Air Canada
  • Air Canada
  • 5-10-19-10
  • 4 total stops
  • 69h 09m total
  • Singapore to Chicago
9-10
  • 9-10
  • 2 total stops
  • 30h 00m total
  • Singapore to Chicago
Highest demand for flights based on searches. 9% potential increase in price (S$ 187 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (S$ 48 potential savings vs. average return price).
Average for return flights in September 2025

Find flight deals to Chicago

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 16 September 2025.

Sun 5-1009:10SIN - ORD
2 stops35h 51mAir Canada
Sun 19-1015:45ORD - SIN
1 stop26h 20mAir Canada
Deal found 13-9S$ 1,051
Sun 12-1009:10SIN - ORD
2 stops35h 48mAir Canada
Sun 19-1008:40ORD - SIN
2 stops33h 25mAir Canada
Deal found 14-9S$ 1,059
Sat 18-1009:10SIN - ORD
1 stop23h 54mAir Canada
Sat 25-1021:12ORD - SIN
2 stops44h 48mAir Canada
Deal found 14-9S$ 1,061
Fri 19-906:15SIN - ORD
1 stop21h 40mANA
Fri 26-917:45ORD - SIN
1 stop23h 55mANA
Deal found 14-9S$ 1,063
Sun 28-909:10SIN - ORD
2 stops35h 51mAir Canada
Sun 19-1013:27ORD - SIN
2 stops28h 38mAir Canada
Deal found 15-9S$ 1,081
Sat 11-1009:10SIN - ORD
2 stops40h 22mAir Canada
Sun 26-1008:45ORD - SIN
2 stops33h 15mAir Canada
Deal found 16-9S$ 1,083
Mon 13-1006:15SIN - ORD
1 stop39h 25mANA
Mon 20-1012:40ORD - SIN
1 stop29h 00mANA
Deal found 14-9S$ 1,085
Sun 28-922:10SIN - ORD
1 stop29h 45mANA
Sun 19-1017:45ORD - SIN
1 stop42h 00mANA
Deal found 15-9S$ 1,095
Sun 5-1022:10SIN - ORD
1 stop30h 00mANA
Sun 19-1017:45ORD - SIN
1 stop42h 00mANA
Deal found 15-9S$ 1,099
Sun 5-1022:30SIN - MDW
2 stops36h 44mDelta
Sun 19-1009:20MDW - SIN
2 stops30h 40mDelta
Deal found 15-9S$ 1,252
Wed 29-1022:30SIN - MDW
2 stops32h 55mDelta
Wed 5-1106:00MDW - SIN
2 stops28h 10mDelta
Deal found 14-9S$ 1,391
Wed 17-901:10SIN - MDW
2 stops33h 26mDelta
Wed 8-1006:00MDW - SIN
2 stops28h 40mDelta
Deal found 14-9S$ 1,534

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 16 September 2025.
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

Sun 28-9

09:10-08:01

2 stops35h 51m

Chicago O'Hare Intl

Sun 19-10

08:51-07:05

1 stop33h 14m

S$ 1,081

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 11-10

09:10-12:32

2 stops40h 22m

Chicago O'Hare Intl

Sun 26-10

08:45-07:00

2 stops33h 15m

S$ 1,083

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 28-9

22:10-14:55

1 stop29h 45m

Chicago O'Hare Intl

Sun 19-10

17:45-00:45

1 stop42h 00m

S$ 1,095

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 1-3

01:25-12:55

1 stop25h 30m

Chicago O'Hare Intl

Wed 18-3

15:35-15:45

1 stop35h 10m

S$ 1,231

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 17-12

22:20-05:00

1 stop20h 40m

Chicago O'Hare Intl

Mon 12-1

06:47-20:15

1 stop23h 28m

S$ 1,232

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 8-10

20:40-11:46

1 stop28h 06m

Chicago O'Hare Intl

Wed 29-10

16:17-07:00

1 stop25h 43m

S$ 1,232

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 14-12

22:20-05:00

1 stop20h 40m

Chicago O'Hare Intl

Mon 12-1

18:29-08:00

1 stop23h 31m

S$ 1,232

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 8-10

06:15-20:04

2 stops26h 49m

Chicago O'Hare Intl

Wed 29-10

08:45-07:00

2 stops33h 15m

S$ 1,238

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 13-12

10:10-21:07

1 stop24h 57m

Chicago O'Hare Intl

Mon 5-1

06:15-20:15

1 stop24h 00m

S$ 1,244

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 10-2

10:40-09:56

2 stops37h 16m

Chicago Midway

Fri 20-2

17:59-00:10

2 stops40h 11m

S$ 1,252

Flights are sorted by cheapest return flights first.

Deals found on 14-9

Showing 1-10 of 36 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

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 12 September 2025.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 6 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 25 hours 40 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 16 September 2025.
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.

Entertainment

8.0

Overall

8.4

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

Entertainment

8.0

Overall

8.4

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak
8.4
Very Good

Entertainment

8.0

Overall

8.4

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

Entertainment

8.0

Overall

8.4

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

Entertainment

8.0

Overall

8.4

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

Entertainment

8.0

Overall

8.4

Comfort

8.3

Boarding

8.4

Crew

8.6

Food

8.1

Reviews

1 / 20
6.0
Good

Anonymous,Aug 2025

BKK - TPE

I bought tickets for myself and my friend and had to argue with the checkin person to get our seats together for the return flights I purchased the tickets together weeks ahead of time and did not expect to have to ask for a supervisor to sit together very disappointed in booking through kayak

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.

  • 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$ 244, while return flights cost around S$ 319.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 371, however they can be found for as little as S$ 249.

  • 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 (24 hours 20 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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