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S$ 699+ 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 12-12. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
10 Nov — 17 Nov1
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 193,031 searches and data was last updated on 5 November 2024.

Fly from

Any airport

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 12-12

15:15-19:45

3 stops42h 30m

S$ 699

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 26-3

19:40-19:35

2 stops36h 55m

S$ 832

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 12-2

13:15-19:35

1 stop20h 20m

S$ 888

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 26-1

10:25-10:10

1 stop37h 45m

S$ 899

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 18-11

01:25-13:00

1 stop25h 35m

S$ 921

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 21-1

22:30-08:40

1 stop24h 10m

S$ 938

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Tue 11-2

01:30-13:08

2 stops25h 38m

S$ 944

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 28-1

02:00-07:40

2 stops43h 40m

S$ 1,199

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 19-1

23:55-11:05

1 stop25h 10m

S$ 1,259

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 29-1

23:45-12:15

3 stops50h 30m

S$ 1,284

Flights are sorted by cheapest first

Deals found on 2-11

Showing 1-10 of 40 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 193,031 searches and data was last updated on 5 November 2024.

Return from

S$ 1,272

One-way from

S$ 738

Popular in

August

Cheapest in

October

Average price

S$ 1,510
Turkish Airlines
  • Turkish Airlines
  • 15-11-29-11
  • 2 total stops
  • 60h 10m total
  • Singapore to Chicago
27-11
  • 27-11
  • 3 total stops
  • 55h 16m total
  • Singapore to Chicago
High demand for flights, 4% 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 5 November 2024.

Fri 15-1110:25SIN - ORD
1 stop37h 45mTurkish Airlines
Fri 29-1120:20ORD - SIN
1 stop22h 25mTurkish Airlines
Deal found 4-11S$ 1,272
Sun 8-1210:10SIN - ORD
1 stop33h 47mUnited Airlines
Wed 8-114:35ORD - SIN
1 stop39h 40mUnited Airlines
Deal found 4-11S$ 1,325
Thu 14-1101:25SIN - ORD
1 stop25h 35mCathay Pacific
Fri 29-1114:40ORD - SIN
2 stops35h 40mCathay Pacific
Deal found 4-11S$ 1,364
Fri 15-1106:40SIN - ORD
2 stops24h 40mMultiple Airlines
Fri 29-1114:40ORD - SIN
1 stop25h 00mMultiple Airlines
Deal found 4-11S$ 1,365
Mon 9-1202:20SIN - ORD
1 stop19h 05mJapan Airlines
Tue 7-107:18ORD - SIN
2 stops27h 32mJapan Airlines
Deal found 4-11S$ 1,414
Sat 7-1201:30SIN - ORD
1 stop21h 00mDelta
Wed 8-107:00ORD - SIN
2 stops32h 00mDelta
Deal found 3-11S$ 1,694
Fri 15-1119:40SIN - ORD
2 stops36h 45mIndiGo
Fri 29-1120:20ORD - SIN
2 stops31h 00mIndiGo
Deal found 4-11S$ 1,802
Thu 19-1208:20SIN - ORD
1 stop36h 10mAir India
Thu 26-1211:00ORD - SIN
1 stop30h 00mAir India
Deal found 4-11S$ 1,803
Thu 14-1103:55SIN - ORD
2 stops39h 07mChina Southern
Thu 28-1112:01ORD - SIN
3 stops38h 49mChina Southern
Deal found 4-11S$ 1,976
Tue 10-1211:00SIN - MDW
2 stops25h 06mDelta
Tue 7-118:28MDW - SIN
2 stops39h 42mDelta
Deal found 4-11S$ 2,123
Thu 14-1102:00SIN - ORD
1 stop26h 30mJetBlue
Fri 29-1119:05ORD - SIN
1 stop23h 40mJetBlue
Deal found 4-11S$ 2,376
Mon 9-1201:40SIN - MDW
2 stops29h 21mMultiple Airlines
Tue 7-114:08MDW - SIN
2 stops28h 52mMultiple Airlines
Deal found 4-11S$ 2,719

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 1 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 23 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 Turkish Airlines, Cathay Pacific and United Airlines.

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 5 November 2024.
Read through reviews of airlines servicing Chicago, such as Turkish Airlines, United Airlines and Delta. 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
1,036 reviews

Comfort

8.3

Food

8.1

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.5

Reviews

1 / 10

Ticket counter agent need to be more patient. Food was not good. It was not good like in the past.. Cabin was too hot.

8.5
Very Good
1,036 reviews
8.5
Very Good
1,036 reviews

Comfort

8.3

Food

8.1

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.5

Reviews

1 / 10

Ticket counter agent need to be more patient. Food was not good. It was not good like in the past.. Cabin was too hot.

8.4
Very Good
1,324 reviews
8.5
Very Good
1,036 reviews

Comfort

8.3

Food

8.1

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.5

Reviews

1 / 10

Ticket counter agent need to be more patient. Food was not good. It was not good like in the past.. Cabin was too hot.

8.4
Very Good
833 reviews
8.5
Very Good
1,036 reviews

Comfort

8.3

Food

8.1

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.5

Reviews

1 / 10

Ticket counter agent need to be more patient. Food was not good. It was not good like in the past.. Cabin was too hot.

8.3
Very Good
1,457 reviews
8.5
Very Good
1,036 reviews

Comfort

8.3

Food

8.1

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.5

Reviews

1 / 10

Ticket counter agent need to be more patient. Food was not good. It was not good like in the past.. Cabin was too hot.

8.1
Very Good
3,540 reviews
8.5
Very Good
1,036 reviews

Comfort

8.3

Food

8.1

Boarding

8.5

Entertainment

8.2

Crew

8.7

Overall

8.5

Reviews

1 / 10

Ticket counter agent need to be more patient. Food was not good. It was not good like in the past.. Cabin was too hot.

As Frank Sinatra crooned, “Chicago is my kind of town.” And many visitors agree. A trip to Chicago is best spent shopping on the Miracle Mile, stepping back in time at the National History Museum, touring the artist’s lofts in the heart of the city, and enjoying some cool jazz at one of Chicago’s many jazz clubs.

Chicago, with its varied and eclectic sampling of modern architecture, rests on the shores of Lake Michigan in the heart of the American Midwest. Flights to Chicago land travellers at either Midway Airport or O’Hare International Airport, both about 30 minutes from downtown Chicago, but a car isn’t needed to get around. Take a taxi or hop the commuter rail from your Chicago flight to downtown and then tour the city by foot. Stop by the Sears Tower, the tallest building in the United States, and take an elevator ride to the Sears Tower Skydeck for unprecedented views of the city.

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$ 76, while return flights cost around S$ 206.

  • 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 (20 hours 55 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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