S$ 626+ Cheap flights to Chicago

— CHI
9 Oct — 16 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

Sat 3-1007:00 -
1 stop20h 43m
Sun 18-1015:40 -
1 stop24h 35m
Deal found 5-9S$ 967
Fri 20-1108:40 -
1 stop19h 57m
Sun 29-1115:30 -
1 stop25h 30m
Deal found 7-9S$ 986
Thu 22-1007:00 -
1 stop20h 43m
Thu 29-1015:30 -
1 stop26h 30m
Deal found 7-9S$ 1,006
Sat 3-1020:05 -
2 stops31h 38m
Sun 18-1015:40 -
1 stop24h 35m
Deal found 5-9S$ 1,018
Mon 5-1006:15 -
2 stops26h 33m
Thu 29-1015:30 -
1 stop26h 30m
Deal found 7-9S$ 1,019
Sat 10-1007:00 -
1 stop26h 06m
Sun 25-1008:49 -
1 stop33h 11m
Deal found 9-9S$ 1,026
Tue 20-1022:00 -
2 stops33h 00m
Tue 27-1009:29 -
2 stops30h 31m
Deal found 5-9S$ 1,435
Tue 6-1007:30 -
2 stops28h 03m
Tue 13-1017:31 -
2 stops41h 24m
Deal found 7-9S$ 1,436
Thu 22-1007:30 -
2 stops41h 24m
Thu 29-1017:09 -
2 stops42h 06m
Deal found 7-9S$ 1,575
Thu 15-1013:55 -
2 stops29h 10m
Wed 28-1010:30 -
2 stops37h 35m
Deal found 4-9S$ 1,638
Mon 5-1013:55 -
2 stops29h 10m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 7-9S$ 1,640
Sun 18-1013:55 -
2 stops34h 20m
Thu 29-1015:55 -
2 stops32h 10m
Deal found 8-9S$ 1,646

Find flight deals to Chicago

Return from

S$ 967

One-way from

S$ 626

Popular in

August

Cheapest in

September

Average price

S$ 1,088
Air Canada
  • Air Canada
  • 3-10-18-10
  • 2 total stops
  • 45h 18m total
  • Singapore to Chicago
Air Canada
  • Air Canada
  • 15-11-31-12
  • 1 total stop
  • 19h 57m total
  • Singapore to Chicago
Highest demand for flights based on searches. 14% potential increase in price (S$ 256 potential increase over avg. return price).
Cheapest flight prices on average. 8% potential price decrease (S$ 112 potential savings vs. average return price).
Average for return flights in September 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

Sat 24-10

20:50-14:37

2 stops30h 47m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 657

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 20-11

08:40-19:52

2 stops25h 12m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 661
Fastest return journey

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 28-1

01:40-08:30

1 stop20h 50m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 712

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Thu 22-10

01:25-09:30

1 stop21h 05m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 713

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Sun 13-9

01:25-23:59

2 stops35h 34m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 717

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Sat 30-1

09:20-20:04

2 stops24h 44m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 757

SingaporeChicago

SIN Singapore Changi - ORD Chicago O'Hare Intl

SINORD

Singapore Changi

Fri 23-10

07:00-06:34

3 stops36h 34m

Chicago O'Hare Intl

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 784

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Fri 23-10

09:00-14:35

3 stops42h 35m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 817

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Sat 24-10

13:10-12:17

3 stops36h 07m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 924

SingaporeChicago

SIN Singapore Changi - MDW Chicago Midway

SINMDW

Singapore Changi

Tue 20-10

13:55-06:05

2 stops29h 10m

Chicago Midway

Wed 31-12

00:00-13:30

Nonstop0h 00m

S$ 951

Flights are sorted by cheapest return flights first.

Deals found on 6-9

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 24 hours 0 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.

Entertainment

8.0

Boarding

8.5

Crew

8.7

Comfort

8.3

Food

8.1

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Entertainment

8.0

Boarding

8.5

Crew

8.7

Comfort

8.3

Food

8.1

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Entertainment

8.0

Boarding

8.5

Crew

8.7

Comfort

8.3

Food

8.1

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Entertainment

8.0

Boarding

8.5

Crew

8.7

Comfort

8.3

Food

8.1

Overall

8.5

Reviews

1 / 20
10.0
Excellent

Padma,Aug 2026

TPE - SFO

Great but could not allow me to do online booking

Entertainment

8.0

Boarding

8.5

Crew

8.7

Comfort

8.3

Food

8.1

Overall

8.5

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$ 219, while return flights cost around S$ 461.

  • 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 (19 hours 57 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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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.

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Yes! Cheapflights helps users easily find flights to Chicago with no change fees.

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