S$ 580+ Cheap flights to Chicago

— CHI
29 Sep — 6 Oct1
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

Sun 11-1007:00 -
1 stop20h 43m
Sun 18-1015:40 -
1 stop24h 35m
Deal found 26-8S$ 948
Tue 6-1007:00 -
1 stop20h 43m
Fri 23-1015:40 -
1 stop24h 35m
Deal found 28-8S$ 956
Sat 3-1007:00 -
1 stop20h 43m
Sun 18-1008:49 -
1 stop31h 26m
Deal found 26-8S$ 957
Tue 13-1007:00 -
1 stop20h 43m
Tue 20-1015:40 -
1 stop24h 35m
Deal found 29-8S$ 993
Sun 18-1007:00 -
1 stop20h 43m
Thu 29-1015:30 -
1 stop26h 30m
Deal found 26-8S$ 995
Tue 29-922:00 -
2 stops33h 33m
Tue 6-1010:12 -
2 stops29h 48m
Deal found 30-8S$ 1,439
Mon 14-901:25 -
2 stops24h 14m
Wed 2-1217:14 -
2 stops37h 11m
Deal found 27-8S$ 1,443
Mon 14-901:25 -
2 stops24h 14m
Sat 28-1118:44 -
2 stops39h 26m
Deal found 27-8S$ 1,538
Sat 17-1013:55 -
2 stops34h 30m
Wed 28-1015:35 -
2 stops32h 30m
Deal found 26-8S$ 1,545
Fri 16-1013:55 -
2 stops28h 55m
Fri 30-1015:55 -
2 stops32h 10m
Deal found 29-8S$ 1,547
Wed 23-913:55 -
2 stops29h 00m
Wed 30-917:15 -
2 stops30h 15m
Deal found 26-8S$ 1,548
Fri 9-1013:55 -
2 stops28h 55m
Fri 16-1019:15 -
2 stops28h 15m
Deal found 25-8S$ 1,551

Find flight deals to Chicago

Return from

S$ 948

One-way from

S$ 568

Popular in

August

Cheapest in

September

Average price

S$ 2,618
Air Canada
  • Air Canada
  • 11-10-18-10
  • 2 total stops
  • 45h 18m total
  • Singapore to Chicago
Air Canada
  • Air Canada
  • 26-11
  • 1 total stop
  • 19h 57m total
  • Singapore to Chicago
Highest demand for flights based on searches. 14% potential increase in price (S$ 262 potential increase over avg. return price).
Cheapest flight prices on average. 8% potential price decrease (S$ 113 potential savings vs. average return price).
Average for return flights in August 2026

Cheapflights Fare Finder

 
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

Fri 16-10

21:00-15:40

1 stop31h 40m

Chicago O'Hare Intl

Thu 29-10

14:10-09:35

1 stop30h 25m

S$ 1,195

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Wed 23-9

21:00-08:35

1 stop24h 35m

Chicago O'Hare Intl

Wed 30-9

20:25-09:40

1 stop24h 15m

S$ 1,226

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 9-10

21:00-08:35

1 stop24h 35m

Chicago O'Hare Intl

Fri 16-10

14:00-09:40

1 stop30h 40m

S$ 1,237

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Mon 14-9

21:00-08:35

1 stop24h 35m

Chicago O'Hare Intl

Fri 27-11

13:10-09:35

1 stop30h 25m

S$ 1,345
Fastest return journey

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 25-9

08:45-20:22

1 stop24h 37m

Chicago O'Hare Intl

Fri 2-10

06:07-18:35

1 stop23h 28m

S$ 1,422

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 29-9

22:00-18:33

2 stops33h 33m

Chicago Midway

Tue 6-10

10:12-05:00

2 stops29h 48m

S$ 1,439

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Thu 17-9

07:30-22:45

2 stops28h 15m

Chicago Midway

Mon 30-11

18:44-00:10

2 stops39h 26m

S$ 1,443

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sun 20-9

22:00-12:39

2 stops27h 39m

Chicago Midway

Mon 30-11

17:13-00:10

2 stops40h 57m

S$ 1,443

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Mon 14-9

01:25-12:39

2 stops24h 14m

Chicago Midway

Tue 1-12

17:14-20:25

2 stops37h 11m

S$ 1,443

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Wed 9-9

08:05-23:30

2 stops28h 25m

Chicago O'Hare Intl

Sat 12-9

09:55-06:10

2 stops55h 15m

S$ 1,462

Flights are sorted by cheapest return flights first.

Deals found on 25-8

Showing 1-10 of 37 resultsSorted by cheapest first
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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

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 27 hours 22 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 and EVA Air.

Rainfall in Chicago 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

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

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.

Boarding

8.5

Crew

8.7

Entertainment

8.0

Food

8.1

Overall

8.5

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Boarding

8.5

Crew

8.7

Entertainment

8.0

Food

8.1

Overall

8.5

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Boarding

8.5

Crew

8.7

Entertainment

8.0

Food

8.1

Overall

8.5

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Boarding

8.5

Crew

8.7

Entertainment

8.0

Food

8.1

Overall

8.5

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Boarding

8.5

Crew

8.7

Entertainment

8.0

Food

8.1

Overall

8.5

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

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$ 221, while return flights cost around S$ 464.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 520, however they can be found for as little as S$ 464.

  • 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 (26 hours 30 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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