S$ 657+ 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 27-10. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
26 Jun — 3 Jul1
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 27 May 2026.

Sat 7-1108:50
SIN
-
ORD
1 stop19h 51m
Air Canada
Sun 22-1115:40
ORD
-
SIN
1 stop25h 20m
Air Canada
Deal found 24-5S$ 1,023
Thu 5-1108:50
SIN
-
ORD
1 stop19h 51m
Air Canada
Tue 17-1115:40
ORD
-
SIN
1 stop25h 20m
Air Canada
Deal found 23-5S$ 1,035
Mon 7-922:00
SIN
-
ORD
1 stop23h 40m
ANA
Mon 28-917:45
ORD
-
SIN
1 stop23h 55m
ANA
Deal found 25-5S$ 1,051
Wed 8-706:15
SIN
-
ORD
2 stops26h 50m
Air Canada
Sun 12-705:00
ORD
-
SIN
2 stops35h 15m
Air Canada
Deal found 24-5S$ 1,067
Tue 8-906:15
SIN
-
ORD
2 stops26h 57m
Air Canada
Tue 29-907:09
ORD
-
SIN
2 stops32h 51m
Air Canada
Deal found 25-5S$ 1,079
Tue 8-922:00
SIN
-
ORD
1 stop23h 40m
ANA
Tue 29-907:44
ORD
-
SIN
2 stops26h 36m
ANA
Deal found 25-5S$ 1,090
Sun 8-1108:50
SIN
-
ORD
1 stop19h 51m
Air Canada
Mon 23-1108:00
ORD
-
SIN
2 stops32h 55m
Air Canada
Deal found 25-5S$ 1,092
Tue 7-707:00
SIN
-
ORD
2 stops50h 05m
Air Canada
Sun 12-705:00
ORD
-
SIN
2 stops35h 15m
Air Canada
Deal found 24-5S$ 1,122
Thu 5-1108:50
SIN
-
ORD
1 stop19h 51m
Air Canada
Wed 18-1115:40
ORD
-
SIN
1 stop25h 20m
Air Canada
Deal found 23-5S$ 1,125
Sun 6-922:00
SIN
-
MDW
2 stops37h 36m
Delta
Mon 28-909:49
MDW
-
SIN
2 stops30h 11m
Delta
Deal found 25-5S$ 1,222
Wed 28-1022:30
SIN
-
MDW
2 stops27h 03m
Delta
Wed 18-1106:00
MDW
-
SIN
2 stops33h 00m
Delta
Deal found 24-5S$ 1,363
Tue 8-907:30
SIN
-
MDW
2 stops27h 16m
Delta
Tue 29-909:30
MDW
-
SIN
2 stops25h 25m
Delta
Deal found 25-5S$ 1,419

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 27 May 2026.

Return from

S$ 973

One-way from

S$ 657

Popular in

August

Cheapest in

February

Average price

S$ 1,367
Air Canada
  • Air Canada
  • 10-11-25-11
  • 2 total stops
  • 45h 11m total
  • Singapore to Chicago
Singapore Airlines
  • Singapore Airlines
  • 27-10
  • 1 total stop
  • 20h 48m total
  • Singapore to Chicago
Highest demand for flights based on searches. 16% potential increase in price (S$ 283 potential increase over avg. return price).
Cheapest flight prices on average. 7% potential price decrease (S$ 105 potential savings vs. average return price).
Average for return flights in May 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 27 May 2026.
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 - ORD

SINORD

Singapore Changi

Sat 19-9

22:00-23:47

2 stops38h 47m

Chicago O'Hare Intl

Tue 22-9

07:05-23:55

2 stops27h 50m

S$ 1,363

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 29-8

01:25-21:58

2 stops33h 33m

Chicago O'Hare Intl

Tue 1-9

17:45-23:55

2 stops41h 10m

S$ 1,420

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 6-7

01:25-23:38

2 stops35h 13m

Chicago O'Hare Intl

Tue 14-7

15:22-19:15

2 stops38h 53m

S$ 1,423

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7-6

13:45-06:20

2 stops29h 35m

Chicago O'Hare Intl

Sun 9-8

20:20-12:35

2 stops27h 15m

S$ 1,505

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sun 7-6

22:00-16:16

2 stops31h 16m

Chicago Midway

Sun 9-8

06:05-05:00

2 stops33h 55m

S$ 1,560

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 7-6

16:05-13:55

1 stop34h 50m

Chicago O'Hare Intl

Sun 9-8

16:00-20:50

1 stop39h 50m

S$ 1,584

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 8-10

01:25-21:45

2 stops33h 20m

Chicago Midway

Sun 11-10

09:55-19:15

2 stops44h 20m

S$ 1,610

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 8-6

13:45-06:20

2 stops29h 35m

Chicago O'Hare Intl

Sat 20-6

20:05-12:35

2 stops27h 30m

S$ 1,626

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 15-8

13:45-05:45

2 stops29h 00m

Chicago Midway

Mon 17-8

20:55-12:35

2 stops26h 40m

S$ 1,631

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Mon 3-8

13:45-05:40

2 stops28h 55m

Chicago Midway

Sat 29-8

18:00-12:35

2 stops29h 35m

S$ 1,698

Flights are sorted by cheapest return flights first.

Deals found on 22-5

Showing 1-10 of 36 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
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 23 hours 27 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 EVA Air.

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 27 May 2026.
See what other customers who have flown with EVA Air,Japan Airlines, andUnited 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.

Crew

8.7

Boarding

8.4

Comfort

8.3

Overall

8.5

Food

8.1

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?

Crew

8.7

Boarding

8.4

Comfort

8.3

Overall

8.5

Food

8.1

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?

Crew

8.7

Boarding

8.4

Comfort

8.3

Overall

8.5

Food

8.1

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?

Crew

8.7

Boarding

8.4

Comfort

8.3

Overall

8.5

Food

8.1

Entertainment

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

TPE - SFO

Why when we’re about to board they suddenly announced the letters ABC to board first .. so what is the use us waiting at the door (with wheelchairs) ended up almost at the end to board and I can see people walking boarding first? Is this something new? You go by letters now?

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$ 270, while return flights cost around S$ 686.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 686, however they can be found for as little as S$ 686.

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

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