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S$ 642+ 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 14-1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
26 Nov — 3 Dec1
1 adult

Find flights to Chicago within your budget

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 207,334 searches and data was last updated on 21 November 2024.

Fly from

Any airport

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 9-2

10:25-10:10

1 stop37h 45m

Chicago O'Hare Intl

Thu 20-2

11:55-17:35

1 stop39h 40m

S$ 1,230

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Sat 8-2

01:30-22:20

2 stops34h 50m

Chicago Midway

Thu 20-2

18:28-00:10

2 stops39h 42m

S$ 1,356

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 8-2

01:30-21:58

2 stops34h 28m

Chicago O'Hare Intl

Thu 20-2

06:15-00:10

2 stops27h 55m

S$ 1,356

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sat 8-2

01:25-13:00

1 stop25h 35m

Chicago O'Hare Intl

Thu 20-2

14:40-20:10

1 stop39h 30m

S$ 1,373

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 14-4

13:10-21:00

1 stop20h 50m

Chicago O'Hare Intl

Sun 4-5

00:30-13:50

1 stop24h 20m

S$ 1,434

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 14-4

13:10-21:00

1 stop20h 50m

Chicago O'Hare Intl

Mon 5-5

18:50-12:00

2 stops28h 10m

S$ 1,453

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 13-1

10:45-15:05

1 stop42h 20m

Chicago O'Hare Intl

Thu 16-1

20:25-20:15

1 stop33h 50m

S$ 1,482

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 13-1

06:35-18:55

2 stops26h 20m

Chicago O'Hare Intl

Thu 16-1

07:15-06:55

2 stops33h 40m

S$ 1,555

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 12-1

02:20-19:31

2 stops31h 11m

Chicago O'Hare Intl

Thu 16-1

10:35-06:40

1 stop30h 05m

S$ 1,586

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 31-12

23:55-11:05

1 stop25h 10m

Chicago O'Hare Intl

Thu 6-3

21:25-17:05

1 stop29h 40m

S$ 1,685

Flights are sorted by cheapest return flights first.

Deals found on 21-11

Showing 1-10 of 38 results
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Flights to Chicago in 2024

Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 207,334 searches and data was last updated on 21 November 2024.

Return from

S$ 1,230

One-way from

S$ 642

Popular in

August

Cheapest in

October

Average price

S$ 1,485
Turkish Airlines
  • Turkish Airlines
  • 9-2-20-2
  • 2 total stops
  • 77h 25m total
  • Singapore to Chicago
14-1
  • 14-1
  • 3 total stops
  • 42h 50m total
  • Singapore to Chicago
High demand for flights, 5% potential price rise
Best time to find cheap flights, 1% potential price drop
Average for return flights in November 2024

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 21 November 2024.

Tue 31-1223:55SIN - ORD
1 stop25h 10mMultiple Airlines
Mon 3-319:05ORD - SIN
1 stop32h 50mMultiple Airlines
Deal found 20-11S$ 1,684
Tue 31-1223:55SIN - ORD
1 stop25h 10mLufthansa
Thu 6-321:25ORD - SIN
1 stop29h 40mLufthansa
Deal found 20-11S$ 1,685
Mon 30-1200:05SIN - ORD
1 stop30h 10mSWISS
Wed 5-316:10ORD - SIN
1 stop35h 45mSWISS
Deal found 20-11S$ 1,859
Tue 31-1210:00SIN - ORD
2 stops23h 55mAir Canada
Thu 20-315:40ORD - SIN
2 stops30h 35mAir Canada
Deal found 20-11S$ 2,037
Mon 30-1201:30SIN - ORD
1 stop21h 00mKorean Air
Tue 18-312:25ORD - SIN
1 stop22h 45mKorean Air
Deal found 20-11S$ 2,279
Tue 31-1208:15SIN - ORD
2 stops25h 24mJapan Airlines
Wed 5-307:18ORD - SIN
2 stops27h 32mJapan Airlines
Deal found 20-11S$ 2,295
Tue 31-1223:15SIN - ORD
2 stops32h 16mBritish Airways
Fri 7-320:20ORD - SIN
2 stops32h 05mBritish Airways
Deal found 20-11S$ 2,478
Mon 30-1203:15SIN - ORD
1 stop25h 15mQatar Airways
Thu 20-319:50ORD - SIN
1 stop23h 55mQatar Airways
Deal found 20-11S$ 2,630
Fri 20-1209:30SIN - ORD
1 stop35h 00mAir India
Fri 27-1211:00ORD - SIN
1 stop31h 10mAir India
Deal found 20-11S$ 5,116
Fri 20-1206:35SIN - ORD
2 stops31h 55mUnited Airlines
Fri 27-1220:20ORD - SIN
1 stop45h 40mUnited Airlines
Deal found 20-11S$ 7,160
Fri 29-1101:30SIN - ORD
2 stops34h 28mDelta
Wed 4-1215:45ORD - SIN
2 stops42h 25mDelta
Deal found 21-11S$ 7,520
Thu 19-1201:25SIN - ORD
1 stop25h 35mCathay Pacific
Fri 27-1214:40ORD - SIN
1 stop32h 25mCathay Pacific
Deal found 20-11S$ 7,869

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.

Travel insights for flights to Chicago

Get recent, data-driven insights about flights to Chicago including ideal travel times, pricing trends, and more.

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 15 November 2024.

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 63 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 27 hours 45 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 Turkish Airlines, United Airlines and Cathay Pacific.

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 21 November 2024.
Read through reviews of airlines servicing Chicago, such as United Airlines, Delta and KLM. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.5
Very Good
1,024 reviews

Crew

8.7

Comfort

8.3

Entertainment

8.2

Food

8.1

Boarding

8.5

Overall

8.5

Reviews

1 / 10

The only reason I gave comfort a good and not an excellent is over something Korean Air has no control. I choose an aisle seat so I can easily stand and walk to the lavatory and so I have only one seat mate to contend with. In my case, I had someone who chose to horn in on my space. At its worst, she laid her head on her companion’s lap with her feet close to me. She made sure her feet were covered with her blanket and scrunched up so she wasn’t exactly in my face. That was good enough for me not to complain to the fight attendants.

8.5
Very Good
1,024 reviews
8.5
Very Good
1,024 reviews

Crew

8.7

Comfort

8.3

Entertainment

8.2

Food

8.1

Boarding

8.5

Overall

8.5

Reviews

1 / 10

The only reason I gave comfort a good and not an excellent is over something Korean Air has no control. I choose an aisle seat so I can easily stand and walk to the lavatory and so I have only one seat mate to contend with. In my case, I had someone who chose to horn in on my space. At its worst, she laid her head on her companion’s lap with her feet close to me. She made sure her feet were covered with her blanket and scrunched up so she wasn’t exactly in my face. That was good enough for me not to complain to the fight attendants.

8.4
Very Good
1,307 reviews
8.5
Very Good
1,024 reviews

Crew

8.7

Comfort

8.3

Entertainment

8.2

Food

8.1

Boarding

8.5

Overall

8.5

Reviews

1 / 10

The only reason I gave comfort a good and not an excellent is over something Korean Air has no control. I choose an aisle seat so I can easily stand and walk to the lavatory and so I have only one seat mate to contend with. In my case, I had someone who chose to horn in on my space. At its worst, she laid her head on her companion’s lap with her feet close to me. She made sure her feet were covered with her blanket and scrunched up so she wasn’t exactly in my face. That was good enough for me not to complain to the fight attendants.

8.4
Very Good
833 reviews
8.5
Very Good
1,024 reviews

Crew

8.7

Comfort

8.3

Entertainment

8.2

Food

8.1

Boarding

8.5

Overall

8.5

Reviews

1 / 10

The only reason I gave comfort a good and not an excellent is over something Korean Air has no control. I choose an aisle seat so I can easily stand and walk to the lavatory and so I have only one seat mate to contend with. In my case, I had someone who chose to horn in on my space. At its worst, she laid her head on her companion’s lap with her feet close to me. She made sure her feet were covered with her blanket and scrunched up so she wasn’t exactly in my face. That was good enough for me not to complain to the fight attendants.

8.3
Very Good
1,460 reviews
8.5
Very Good
1,024 reviews

Crew

8.7

Comfort

8.3

Entertainment

8.2

Food

8.1

Boarding

8.5

Overall

8.5

Reviews

1 / 10

The only reason I gave comfort a good and not an excellent is over something Korean Air has no control. I choose an aisle seat so I can easily stand and walk to the lavatory and so I have only one seat mate to contend with. In my case, I had someone who chose to horn in on my space. At its worst, she laid her head on her companion’s lap with her feet close to me. She made sure her feet were covered with her blanket and scrunched up so she wasn’t exactly in my face. That was good enough for me not to complain to the fight attendants.

8.1
Very Good
3,489 reviews
8.5
Very Good
1,024 reviews

Crew

8.7

Comfort

8.3

Entertainment

8.2

Food

8.1

Boarding

8.5

Overall

8.5

Reviews

1 / 10

The only reason I gave comfort a good and not an excellent is over something Korean Air has no control. I choose an aisle seat so I can easily stand and walk to the lavatory and so I have only one seat mate to contend with. In my case, I had someone who chose to horn in on my space. At its worst, she laid her head on her companion’s lap with her feet close to me. She made sure her feet were covered with her blanket and scrunched up so she wasn’t exactly in my face. That was good enough for me not to complain to the fight attendants.

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, Turkish 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$ 74, while return flights cost around S$ 210.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 214, however they can be found for as little as S$ 156.

  • 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 46 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).

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