S$ 652+ 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 25-1. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
6 Dec — 13 Dec1
1 adult
1 adult, Economy, 0 bags

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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 6 November 2025.

Wed 19-1122:20SIN - ORD
1 stop28h 04mUnited Airlines
Sat 22-1121:10ORD - SIN
1 stop44h 50mUnited Airlines
Deal found 5-11S$ 1,209
Fri 7-1110:10SIN - ORD
1 stop28h 49mUnited Airlines
Sun 23-1118:25ORD - SIN
1 stop23h 35mUnited Airlines
Deal found 5-11S$ 1,210
Wed 5-1110:10SIN - ORD
1 stop20h 45mUnited Airlines
Thu 6-1119:35ORD - SIN
1 stop34h 40mUnited Airlines
Deal found 4-11S$ 1,212
Sat 13-1210:25SIN - ORD
1 stop37h 40mTurkish Airlines
Mon 5-111:50ORD - SIN
1 stop32h 10mTurkish Airlines
Deal found 5-11S$ 1,376
Wed 3-1222:30SIN - ORD
2 stops32h 45mDelta
Thu 11-1220:40ORD - SIN
2 stops37h 30mDelta
Deal found 5-11S$ 1,379
Sat 6-1220:15SIN - ORD
1 stop30h 40mCathay Pacific
Thu 11-1214:35ORD - SIN
1 stop31h 20mCathay Pacific
Deal found 5-11S$ 1,393
Tue 16-1222:20SIN - ORD
1 stop30h 28mUnited Airlines
Wed 31-1206:15ORD - SIN
1 stop24h 00mUnited Airlines
Deal found 3-11S$ 1,401
Tue 2-1208:50SIN - ORD
2 stops37h 10mAir Canada
Tue 9-1215:40ORD - SIN
1 stop25h 20mAir Canada
Deal found 4-11S$ 1,406
Tue 2-1222:20SIN - ORD
1 stop38h 50mUnited Airlines
Tue 9-1206:55ORD - SIN
1 stop23h 20mUnited Airlines
Deal found 4-11S$ 1,408
Fri 7-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Sun 23-1117:25MDW - SIN
2 stops28h 40mMultiple Airlines
Deal found 5-11S$ 1,592
Fri 14-1115:45SIN - MDW
2 stops27h 30mMultiple Airlines
Tue 17-216:40MDW - SIN
2 stops29h 25mMultiple Airlines
Deal found 5-11S$ 1,684
Wed 19-1113:15SIN - MDW
2 stops29h 45mMultiple Airlines
Sat 22-1119:00MDW - SIN
2 stops27h 05mMultiple Airlines
Deal found 5-11S$ 1,827

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, 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 6 November 2025.

Return from

S$ 1,195

One-way from

S$ 652

Popular in

January

Cheapest in

October

Average price

S$ 1,261
Air India
  • Air India
  • 25-1-30-1
  • 3 total stops
  • 84h 35m total
  • Singapore to Chicago
IndiGo
  • IndiGo
  • 25-1
  • 2 total stops
  • 45h 10m total
  • Singapore to Chicago
Highest demand for flights based on searches. 11% potential increase in price (S$ 180 potential increase over avg. return price).
Cheapest flight prices on average. 3% potential price decrease (S$ 46 potential savings vs. average return price).
Average for return flights in November 2025

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 6 November 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Singapore

Route

Depart

Return

Price

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 16-4

20:40-06:27

1 stop22h 47m

Chicago O'Hare Intl

Mon 20-4

21:05-18:25

1 stop32h 20m

S$ 1,209

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 21-4

20:40-06:27

1 stop22h 47m

Chicago O'Hare Intl

Wed 6-5

14:25-06:45

1 stop27h 20m

S$ 1,209

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Tue 10-2

10:10-23:14

1 stop27h 04m

Chicago O'Hare Intl

Fri 20-2

18:17-08:00

1 stop23h 43m

S$ 1,213

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 19-4

01:50-14:25

1 stop25h 35m

Chicago O'Hare Intl

Tue 5-5

16:00-15:05

1 stop34h 05m

S$ 1,229

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 9-2

01:25-12:55

1 stop25h 30m

Chicago O'Hare Intl

Fri 20-2

14:35-05:40

1 stop25h 05m

S$ 1,230

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Wed 15-4

01:10-09:40

1 stop21h 30m

Chicago O'Hare Intl

Mon 20-4

12:20-23:40

1 stop22h 20m

S$ 1,236

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Thu 16-4

09:10-12:53

1 stop40h 43m

Chicago O'Hare Intl

Mon 20-4

08:45-00:45

2 stops27h 00m

S$ 1,361

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Mon 20-4

01:10-09:40

1 stop21h 30m

Chicago O'Hare Intl

Wed 6-5

07:30-05:00

2 stops32h 30m

S$ 1,372

SingaporeChicago

SIN - ORD

SINORD

Singapore Changi

Sun 19-4

01:10-09:40

1 stop21h 30m

Chicago O'Hare Intl

Tue 5-5

06:00-23:40

2 stops28h 40m

S$ 1,375

SingaporeChicago

SIN - MDW

SINMDW

Singapore Changi

Thu 16-4

07:30-13:07

2 stops42h 37m

Chicago Midway

Mon 20-4

09:20-23:40

2 stops25h 20m

S$ 1,414

Flights are sorted by cheapest return flights first.

Deals found on 5-11

Showing 1-10 of 33 results
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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 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, Japan Airlines and ANA.

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 6 November 2025.
See what other customers who have flown with EVA Air, ANA, 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.

Food

8.1

Entertainment

8.0

Overall

8.4

Boarding

8.4

Crew

8.6

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

Food

8.1

Entertainment

8.0

Overall

8.4

Boarding

8.4

Crew

8.6

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.
8.4
Very Good

Food

8.1

Entertainment

8.0

Overall

8.4

Boarding

8.4

Crew

8.6

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

Food

8.1

Entertainment

8.0

Overall

8.4

Boarding

8.4

Crew

8.6

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

Food

8.1

Entertainment

8.0

Overall

8.4

Boarding

8.4

Crew

8.6

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

Food

8.1

Entertainment

8.0

Overall

8.4

Boarding

8.4

Crew

8.6

Comfort

8.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2025

TPE - YYZ

All was well. Despite the flight being delayed a few minutes, passengers were made sure to be informed and updated on the status of the delay.

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$ 249, while return flights cost around S$ 81.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 1,645, however they can be found for as little as S$ 81.

  • 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 (22 hours 38 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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