S$ 659+ 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 13-11. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
16 Nov — 23 Nov1
1 adult
1 adult, Economy

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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 17 October 2025.

Mon 10-1100:40SIN - ORD
2 stops44h 48mMultiple Airlines
Sat 15-1121:22ORD - SIN
2 stops36h 18mMultiple Airlines
Deal found 17-10S$ 973
Sun 9-1121:00SIN - ORD
2 stops31h 41mAir Canada
Thu 13-1115:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 15-10S$ 1,033
Mon 27-1023:10SIN - ORD
2 stops52h 31mAir Canada
Thu 13-1115:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 15-10S$ 1,071
Mon 27-1022:20SIN - ORD
1 stop30h 50mANA
Sun 16-1116:25ORD - SIN
1 stop35h 10mANA
Deal found 14-10S$ 1,074
Mon 27-1023:10SIN - ORD
2 stops52h 31mAir Canada
Sun 16-1115:40ORD - SIN
2 stops43h 15mAir Canada
Deal found 14-10S$ 1,117
Sun 16-1108:50SIN - ORD
1 stop19h 51mAir Canada
Thu 20-1107:05ORD - SIN
2 stops33h 55mAir Canada
Deal found 15-10S$ 1,140
Tue 11-1108:50SIN - ORD
1 stop19h 51mAir Canada
Sat 15-1117:55ORD - SIN
2 stops47h 05mAir Canada
Deal found 17-10S$ 1,142
Mon 27-1022:30SIN - MDW
2 stops36h 44mDelta
Sun 16-1106:00MDW - SIN
2 stops33h 00mDelta
Deal found 14-10S$ 1,388
Sun 9-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Thu 13-1117:25MDW - SIN
2 stops28h 40mMultiple Airlines
Deal found 15-10S$ 1,557
Sat 25-1013:10SIN - MDW
2 stops28h 50mMultiple Airlines
Sun 9-1118:05MDW - SIN
2 stops28h 00mMultiple Airlines
Deal found 16-10S$ 1,680
Fri 14-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Fri 21-1118:05MDW - SIN
2 stops28h 00mMultiple Airlines
Deal found 14-10S$ 2,066
Mon 1-1222:30SIN - MDW
2 stops27h 25mDelta
Mon 8-1206:00MDW - SIN
2 stops33h 00mDelta
Deal found 17-10S$ 2,194

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 17 October 2025.

Return from

S$ 1,033

One-way from

S$ 659

Popular in

January

Cheapest in

October

Average price

S$ 1,190
Air Canada
  • Air Canada
  • 9-11-13-11
  • 3 total stops
  • 57h 01m total
  • Singapore to Chicago
13-11
  • 13-11
  • 2 total stops
  • 30h 13m total
  • Singapore to Chicago
Highest demand for flights based on searches. 11% potential increase in price (S$ 179 potential increase over avg. return price).
Cheapest flight prices on average. 3% potential price decrease (S$ 46 potential savings vs. average return price).
Average for return flights in October 2025

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 17 October 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

Mon 22-12

22:20-05:46

1 stop21h 26m

Chicago O'Hare Intl

Tue 6-1

18:29-20:15

1 stop35h 46m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 6-2

10:10-17:01

1 stop20h 51m

Chicago O'Hare Intl

Sat 14-2

15:55-20:15

1 stop38h 20m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Fri 14-11

22:20-12:24

1 stop28h 04m

Chicago O'Hare Intl

Tue 25-11

18:25-08:00

1 stop23h 35m

S$ 1,204

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-2

22:20-13:10

1 stop28h 50m

Chicago O'Hare Intl

Fri 20-2

06:35-20:15

1 stop23h 40m

S$ 1,206

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 1-4

09:00-06:11

1 stop34h 11m

Chicago O'Hare Intl

Thu 16-4

06:15-18:25

1 stop23h 10m

S$ 1,206

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 6-4

09:00-06:11

1 stop34h 11m

Chicago O'Hare Intl

Mon 20-4

06:15-18:25

1 stop23h 10m

S$ 1,206

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 13-12

10:10-21:07

1 stop24h 57m

Chicago O'Hare Intl

Mon 5-1

22:00-20:15

1 stop32h 15m

S$ 1,217

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 30-3

01:50-14:25

1 stop25h 35m

Chicago O'Hare Intl

Wed 15-4

18:50-09:40

2 stops25h 50m

S$ 1,234

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9-2

01:25-12:55

1 stop25h 30m

Chicago O'Hare Intl

Fri 20-2

14:35-05:40

1 stop25h 05m

S$ 1,262

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 15-4

01:10-09:40

1 stop21h 30m

Chicago O'Hare Intl

Mon 20-4

09:30-23:40

2 stops25h 10m

S$ 1,384

Flights are sorted by cheapest return flights first.

Deals found on 16-10

Showing 1-10 of 37 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 10 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 17 October 2025.
See what other customers who have flown with EVA Air, ANA, 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.

Overall

8.4

Comfort

8.3

Food

8.0

Boarding

8.4

Crew

8.6

Entertainment

8.0

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

Overall

8.4

Comfort

8.3

Food

8.0

Boarding

8.4

Crew

8.6

Entertainment

8.0

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

Overall

8.4

Comfort

8.3

Food

8.0

Boarding

8.4

Crew

8.6

Entertainment

8.0

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

Overall

8.4

Comfort

8.3

Food

8.0

Boarding

8.4

Crew

8.6

Entertainment

8.0

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

Overall

8.4

Comfort

8.3

Food

8.0

Boarding

8.4

Crew

8.6

Entertainment

8.0

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

Overall

8.4

Comfort

8.3

Food

8.0

Boarding

8.4

Crew

8.6

Entertainment

8.0

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$ 246, while return flights cost around S$ 322.

  • 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 (20 hours 50 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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