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Cheap flights to Chicago from S$ 808

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 14-10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CMH — CHI
2 May — 9 May1
1 adult
Thu 2-5
Thu 9-5

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 200,158 searches and data was last updated on 27 April 2024.

Popular in

August

Cheapest in

October

Average price

S$ 2,001

Return from

S$ 1,357

One-way from

S$ 808
High demand for flights, 8% potential price rise
Best time to find cheap flights, 2% potential price drop
Average for return flights in April 2024
From Singapore Changi to Chicago
One-way flight from Singapore Changi (SIN) to Chicago

Cheap flights to Chicago in April & May 2024

Discover affordable flights and deals to Chicago in April and May 2024. In the last 7 days, Cheapflights users made a total of 200,158 searches and data was last updated on 27 April 2024.
The deals listed below are some of the cheapest flights available to Chicago in April and May 2024. If these deals fall outside of your budget, be sure to come back soon as prices update often.
Mon 27-521:50SIN - ORD
2 stops29h 15mAmerican Airlines
Tue 30-712:25ORD - SIN
1 stop28h 50mAmerican Airlines
Deal found 26-4S$ 1,504
Mon 27-521:50SIN - ORD
2 stops29h 15mAmerican Airlines
Tue 30-709:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 26-4S$ 1,507
Wed 1-508:05SIN - ORD
2 stops25h 40mAmerican Airlines
Sun 12-509:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 26-4S$ 1,516
Sat 4-508:05SIN - ORD
2 stops28h 29mJapan Airlines
Fri 10-506:00ORD - SIN
2 stops29h 20mJapan Airlines
Deal found 26-4S$ 1,597
Fri 24-523:25SIN - ORD
1 stop25h 50mMultiple Airlines
Sun 16-615:50ORD - SIN
1 stop36h 05mMultiple Airlines
Deal found 26-4S$ 1,599
Tue 30-401:50SIN - ORD
2 stops42h 34mAmerican Airlines
Sun 12-510:05ORD - SIN
2 stops42h 30mAmerican Airlines
Deal found 26-4S$ 1,610
Thu 23-501:50SIN - ORD
2 stops26h 16mAmerican Airlines
Sun 16-606:00ORD - SIN
2 stops35h 15mAmerican Airlines
Deal found 26-4S$ 1,629
Fri 24-508:05SIN - ORD
2 stops28h 23mAmerican Airlines
Sun 16-614:45ORD - SIN
2 stops37h 50mAmerican Airlines
Deal found 26-4S$ 1,632
Sun 26-501:50SIN - ORD
2 stops25h 15mAmerican Airlines
Tue 30-712:25ORD - SIN
1 stop28h 50mAmerican Airlines
Deal found 26-4S$ 1,659

Chicago 2024 flight deals

Explore flight deals for Chicago in 2024, offering the best prices and options to suit your preferences. In the last 7 days, Cheapflights users made a total of 200,158 searches and data were last updated on 27 April 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back in a little while for more flight options.
Sat 21-913:10SIN - ORD
1 stop20h 35mEVA Air
Fri 27-900:30ORD - SIN
1 stop22h 30mEVA Air
Deal found 26-4S$ 1,357
Sat 21-908:35SIN - ORD
1 stop35h 50mAir India
Sat 28-912:00ORD - SIN
1 stop30h 30mAir India
Deal found 26-4S$ 1,435
Wed 27-1108:20SIN - ORD
1 stop36h 10mAir India
Sun 8-1212:30ORD - SIN
1 stop43h 15mAir India
Deal found 26-4S$ 1,445
Fri 20-901:50SIN - ORD
1 stop20h 20mAmerican Airlines
Sat 28-909:55ORD - SIN
2 stops25h 25mAmerican Airlines
Deal found 26-4S$ 1,493
Sat 21-908:05SIN - ORD
2 stops24h 35mAmerican Airlines
Sat 28-909:55ORD - SIN
2 stops25h 25mAmerican Airlines
Deal found 26-4S$ 1,494
Mon 27-521:50SIN - ORD
2 stops29h 15mAmerican Airlines
Tue 30-712:25ORD - SIN
1 stop28h 50mAmerican Airlines
Deal found 26-4S$ 1,504
Mon 27-521:50SIN - ORD
2 stops29h 15mAmerican Airlines
Tue 30-709:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 26-4S$ 1,507
Wed 12-601:50SIN - ORD
2 stops30h 45mJapan Airlines
Mon 17-606:00ORD - SIN
2 stops35h 15mJapan Airlines
Deal found 26-4S$ 1,515
Wed 1-508:05SIN - ORD
2 stops25h 40mAmerican Airlines
Sun 12-509:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 26-4S$ 1,516

Flights to Chicago departing soon

Discover available last-minute flight options to Chicago, providing immediate availability and potentially lower prices. In the last 7 days, Cheapflights users made a total of 200,158 searches and data was last updated on 27 April 2024.
Browse through available last-minute flights traveling to Chicago. Make sure to double check the price, time, and destination to confirm all are correct.
Wed 1-508:05SIN - ORD
2 stops25h 40mAmerican Airlines
Sun 12-509:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 26-4S$ 1,516
Sat 4-508:05SIN - ORD
2 stops28h 29mJapan Airlines
Fri 10-506:00ORD - SIN
2 stops29h 20mJapan Airlines
Deal found 26-4S$ 1,597
Sat 4-509:00SIN - ORD
2 stops25h 23mUnited Airlines
Fri 10-506:10ORD - SIN
1 stop23h 35mUnited Airlines
Deal found 26-4S$ 1,771
Sat 4-521:00SIN - ORD
1 stop30h 42mUnited Airlines
Fri 10-506:10ORD - SIN
1 stop23h 35mUnited Airlines
Deal found 26-4S$ 1,797
Wed 1-509:00SIN - ORD
3 stops36h 20mUnited Airlines
Sun 12-516:11ORD - SIN
2 stops37h 34mUnited Airlines
Deal found 26-4S$ 1,831
Wed 1-523:25SIN - ORD
2 stops26h 20mMultiple Airlines
Sun 12-519:15ORD - SIN
1 stop32h 40mMultiple Airlines
Deal found 26-4S$ 1,862
Wed 1-523:35SIN - ORD
2 stops25h 25mSWISS
Sun 12-519:15ORD - SIN
1 stop32h 40mSWISS
Deal found 26-4S$ 1,869
Wed 1-521:00SIN - ORD
1 stop40h 56mUnited Airlines
Sun 12-508:50ORD - SIN
1 stop44h 55mUnited Airlines
Deal found 26-4S$ 1,914
Wed 1-523:35SIN - ORD
1 stop29h 30mSWISS
Sun 12-519:15ORD - SIN
1 stop32h 40mSWISS
Deal found 26-4S$ 1,925

One-way flights to Chicago

Explore one-way flight options to Chicago for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 200,158 searches and data was last updated on 27 April 2024.
These are some of the best available deals on flights to Chicago. If you're in need of a round-trip flight to Chicago instead, make sure to update the search form at the top of page.
Mon 14-1014:40SIN - ORD
3 stops56h 34mMultiple Airlines
Deal found 25-4S$ 808
Sun 13-1013:10SIN - ORD
1 stop20h 35mEVA Air
Deal found 25-4S$ 874
Sat 12-1013:10SIN - ORD
1 stop20h 35mEVA Air
Deal found 25-4S$ 887
Fri 11-1013:10SIN - ORD
1 stop20h 35mEVA Air
Deal found 25-4S$ 921
Sat 6-719:45SIN - ORD
2 stops35h 00mIndiGo
Deal found 26-4S$ 947
Sun 13-1000:30SIN - ORD
2 stops46h 44mMultiple Airlines
Deal found 25-4S$ 972
Fri 11-1013:05SIN - ORD
2 stops44h 40mMultiple Airlines
Deal found 25-4S$ 979
Mon 14-1015:20SIN - ORD
2 stops42h 25mMultiple Airlines
Deal found 25-4S$ 984
Sat 18-501:45SIN - ORD
1 stop25h 40mCathay Pacific
Deal found 26-4S$ 1,109

Average price of flights to Chicago by month

Plan your trip to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight to Chicago is currently S$ 942 while a return flight costs S$ 1,559. Price data was last updated on 21 April 2024.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

-5 - 23 °C

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).

When is the best time to book a flight to Chicago?

Use this chart to determine the optimal time to book a return flight to Chicago. Price data was last updated on 28 January 2024.
To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 44 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.
Search Deals

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly return to Chicago. Price data was last updated on 21 April 2024.
Morning
Midday
Afternoon
Evening
All times are departure.
Users looking for the lowest fares to Chicago should consider flying on Thursday at midday, when prices are typically cheapest. Budget-minded travellers will want to avoid Saturday evenings, when prices are usually at their highest.
Search Deals

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 April 2024.
Read through reviews of airlines servicing Chicago, such as EVA Air, Air India and American Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.4
Very Good
1,553 reviews

Boarding

8.4

Food

7.9

Entertainment

8.0

Comfort

8.2

Crew

8.6

Overall

8.4

Reviews

1 / 10

Last row ..eat the last when everybody else finished their meals

8.4
Very Good
1,553 reviews
8.4
Very Good
1,553 reviews

Boarding

8.4

Food

7.9

Entertainment

8.0

Comfort

8.2

Crew

8.6

Overall

8.4

Reviews

1 / 10

Last row ..eat the last when everybody else finished their meals

8.3
Very Good
1,486 reviews
8.4
Very Good
1,553 reviews

Boarding

8.4

Food

7.9

Entertainment

8.0

Comfort

8.2

Crew

8.6

Overall

8.4

Reviews

1 / 10

Last row ..eat the last when everybody else finished their meals

8.3
Very Good
1,479 reviews
8.4
Very Good
1,553 reviews

Boarding

8.4

Food

7.9

Entertainment

8.0

Comfort

8.2

Crew

8.6

Overall

8.4

Reviews

1 / 10

Last row ..eat the last when everybody else finished their meals

8.1
Very Good
4,064 reviews
8.4
Very Good
1,553 reviews

Boarding

8.4

Food

7.9

Entertainment

8.0

Comfort

8.2

Crew

8.6

Overall

8.4

Reviews

1 / 10

Last row ..eat the last when everybody else finished their meals

8.1
Very Good
10,951 reviews
8.4
Very Good
1,553 reviews

Boarding

8.4

Food

7.9

Entertainment

8.0

Comfort

8.2

Crew

8.6

Overall

8.4

Reviews

1 / 10

Last row ..eat the last when everybody else finished their meals

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.

  • What does ORD mean?

    Chicago O'Hare Intl Airport is ORD. This code is created by the International Air Transport Association (IATA) and airlines use IATA codes to identify the departing or arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight destination and their unique identifiers/IATA codes.

  • 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 Airport is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl Airport typically cost S$ 122, while return flights cost around S$ 321.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 1,407, however they can be found for as little as S$ 438.

  • Where does the fastest flight to Chicago depart from?

    For those looking to save time traveling to Chicago, Singapore offers the quickest one-way flight (20 hours 30 minutes).

  • Does Chicago O'Hare Intl Airport have rental cars?

    Yes. Those touching down at Chicago O'Hare Intl Airport can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to Chicago O'Hare Intl Airport?

    Yes. Chicago O'Hare Intl Airport has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl Airport (0.0 km away from Chicago O'Hare Intl Airport).

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