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Cheap flights to Chicago from S$ 786

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 4-9. 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.
BOS — CHI
22 Jun — 29 Jun1
1 adult
Sat 22-6
Sat 29-6

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 202,614 searches and data was last updated on 17 June 2024.

Popular in

August

Cheapest in

February

Average price

S$ 2,021

Return from

S$ 1,366

One-way from

S$ 786
High demand for flights, 13% potential price rise
Best time to find cheap flights, 3% potential price drop
Average for return flights in June 2024
From Singapore Changi to Chicago
One-way flight from Singapore Changi (SIN) to Chicago

Cheap flights to Chicago in June & July 2024

Discover affordable flights and deals to Chicago in June and July 2024. In the last 7 days, Cheapflights users made a total of 202,614 searches and data was last updated on 17 June 2024.
The deals listed below are some of the cheapest flights available to Chicago in June and July 2024. If these deals fall outside of your budget, be sure to come back soon as prices update often.
Mon 15-708:05SIN - ORD
2 stops24h 54mAmerican Airlines
Mon 22-712:25ORD - SIN
1 stop28h 50mAmerican Airlines
Deal found 16-6S$ 1,608
Mon 15-708:05SIN - ORD
2 stops24h 54mAmerican Airlines
Mon 22-709:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 16-6S$ 1,611
Mon 15-708:05SIN - ORD
2 stops29h 14mJapan Airlines
Tue 6-812:25ORD - SIN
1 stop28h 50mJapan Airlines
Deal found 16-6S$ 1,616
Mon 24-608:05SIN - ORD
2 stops24h 31mAmerican Airlines
Wed 7-812:25ORD - SIN
1 stop28h 50mAmerican Airlines
Deal found 16-6S$ 1,734
Mon 24-608:05SIN - ORD
2 stops24h 30mAmerican Airlines
Wed 7-808:10ORD - SIN
2 stops27h 10mAmerican Airlines
Deal found 16-6S$ 1,742
Sat 13-701:50SIN - ORD
2 stops23h 43mAmerican Airlines
Sun 21-709:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 16-6S$ 1,784
Mon 15-708:45SIN - ORD
1 stop29h 00mUnited Airlines
Tue 6-811:10ORD - SIN
3 stops30h 05mUnited Airlines
Deal found 16-6S$ 1,799
Sun 14-708:05SIN - ORD
2 stops24h 24mAmerican Airlines
Sun 21-709:45ORD - SIN
2 stops25h 35mAmerican Airlines
Deal found 16-6S$ 1,802
Mon 24-621:00SIN - ORD
1 stop23h 30mUnited Airlines
Wed 7-806:05ORD - SIN
1 stop23h 40mUnited Airlines
Deal found 16-6S$ 1,817

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 202,614 searches and data were last updated on 17 June 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 16-6S$ 1,366
Tue 17-901:50SIN - ORD
1 stop20h 20mJapan Airlines
Mon 23-912:05ORD - SIN
1 stop29h 10mJapan Airlines
Deal found 17-6S$ 1,396
Tue 17-901:50SIN - ORD
1 stop20h 20mJapan Airlines
Mon 23-910:00ORD - SIN
2 stops42h 35mJapan Airlines
Deal found 17-6S$ 1,403
Sun 18-808:05SIN - ORD
2 stops34h 03mJapan Airlines
Mon 19-812:25ORD - SIN
1 stop40h 10mJapan Airlines
Deal found 17-6S$ 1,416
Wed 11-901:50SIN - ORD
1 stop20h 20mJapan Airlines
Thu 19-912:05ORD - SIN
1 stop29h 10mJapan Airlines
Deal found 17-6S$ 1,477
Fri 15-1123:25SIN - ORD
1 stop24h 45mTurkish Airlines
Fri 29-1120:20ORD - SIN
1 stop22h 05mTurkish Airlines
Deal found 16-6S$ 1,478
Tue 12-1111:00SIN - ORD
1 stop35h 30mKorean Air
Tue 26-1111:25ORD - SIN
1 stop27h 35mKorean Air
Deal found 16-6S$ 1,481
Thu 14-1115:45SIN - ORD
2 stops27h 15mMultiple Airlines
Tue 26-1119:13ORD - SIN
2 stops26h 57mMultiple Airlines
Deal found 16-6S$ 1,484
Wed 11-901:50SIN - ORD
1 stop20h 20mAmerican Airlines
Thu 19-910:00ORD - SIN
2 stops25h 20mAmerican Airlines
Deal found 17-6S$ 1,491

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 202,614 searches and data was last updated on 17 June 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.
Mon 24-608:05SIN - ORD
2 stops24h 31mAmerican Airlines
Wed 7-812:25ORD - SIN
1 stop28h 50mAmerican Airlines
Deal found 16-6S$ 1,734
Mon 24-608:05SIN - ORD
2 stops24h 30mAmerican Airlines
Wed 7-808:10ORD - SIN
2 stops27h 10mAmerican Airlines
Deal found 16-6S$ 1,742
Mon 24-621:00SIN - ORD
1 stop23h 30mUnited Airlines
Wed 7-806:05ORD - SIN
1 stop23h 40mUnited Airlines
Deal found 16-6S$ 1,817
Sun 23-602:15SIN - ORD
2 stops44h 57mQatar Airways
Wed 7-819:40ORD - SIN
1 stop36h 05mQatar Airways
Deal found 16-6S$ 2,613
Sun 23-601:10SIN - ORD
2 stops33h 47mDelta
Wed 7-819:55ORD - SIN
2 stops38h 45mDelta
Deal found 16-6S$ 2,644
Mon 24-613:10SIN - ORD
1 stop20h 50mEVA Air
Tue 6-800:30ORD - SIN
1 stop22h 30mEVA Air
Deal found 16-6S$ 2,678
Sun 23-602:15SIN - ORD
1 stop26h 10mMultiple Airlines
Wed 7-819:40ORD - SIN
1 stop36h 05mMultiple Airlines
Deal found 16-6S$ 2,735
Sun 23-602:00SIN - ORD
2 stops43h 05mEthiopian Air
Wed 7-813:28ORD - SIN
3 stops36h 22mEthiopian Air
Deal found 16-6S$ 3,168

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 202,614 searches and data was last updated on 17 June 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.
Wed 4-922:15SIN - ORD
2 stops32h 48mMultiple Airlines
Deal found 16-6S$ 786
Wed 4-922:15SIN - ORD
2 stops32h 48mMultiple Airlines
Deal found 16-6S$ 787
Wed 4-914:40SIN - ORD
3 stops40h 23mMultiple Airlines
Deal found 16-6S$ 829
Wed 4-907:15SIN - ORD
3 stops47h 48mMultiple Airlines
Deal found 16-6S$ 845
Tue 20-800:55SIN - ORD
3 stops55h 23mMultiple Airlines
Deal found 16-6S$ 862
Wed 21-800:55SIN - ORD
3 stops55h 23mMultiple Airlines
Deal found 16-6S$ 882
Tue 3-900:40SIN - ORD
2 stops30h 23mMultiple Airlines
Deal found 16-6S$ 906
Wed 10-715:10SIN - ORD
2 stops28h 10mMultiple Airlines
Deal found 17-6S$ 931
Mon 8-720:55SIN - ORD
3 stops58h 24mMultiple Airlines
Deal found 16-6S$ 940

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 202,614 searches and data was last updated on 17 June 2024.

Fly from

Any airport

Budget

S$ 1,366 - S$ 1,564

Route

Depart

Return

Price

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Sat 21-9

1 stop20h 35m

Chicago O'Hare Intl

Fri 27-9

1 stop22h 30m

S$ 1,366

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Tue 17-9

1 stop20h 20m

Chicago O'Hare Intl

Mon 23-9

1 stop29h 10m

S$ 1,396

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Fri 15-11

1 stop24h 45m

Chicago O'Hare Intl

Fri 29-11

1 stop22h 05m

S$ 1,478

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Tue 12-11

1 stop35h 30m

Chicago O'Hare Intl

Tue 26-11

1 stop27h 35m

S$ 1,481

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Thu 14-11

2 stops27h 15m

Chicago O'Hare Intl

Tue 26-11

2 stops26h 57m

S$ 1,484

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Wed 11-9

1 stop20h 20m

Chicago O'Hare Intl

Thu 19-9

2 stops25h 20m

S$ 1,491

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Thu 14-11

1 stop24h 00m

Chicago O'Hare Intl

Thu 28-11

2 stops33h 00m

S$ 1,547

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Sat 21-9

1 stop20h 55m

Chicago O'Hare Intl

Sat 28-9

1 stop24h 25m

S$ 1,549

Singapore ChangiChicago O'Hare Intl

SIN - ORD

SINORD

Singapore Changi

Mon 11-11

1 stop30h 10m

Chicago O'Hare Intl

Thu 28-11

1 stop32h 45m

S$ 1,564

Flights are sorted by cheapest first

Deals found on 16-6

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.

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 14 June 2024.
To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 88 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 9 June 2024.
Morning
Midday
Afternoon
Evening
All times are departure.
Users looking for the lowest fares to Chicago should consider flying on Saturday 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 17 June 2024.
Read through reviews of airlines servicing Chicago, such as EVA Air, Cathay Pacific and Qatar Airways. 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
1,124 reviews

Boarding

8.6

Crew

8.8

Overall

8.5

Food

8.1

Comfort

8.3

Entertainment

8.2

Reviews

1 / 10

I like the crews’ services, especially for sr citizens who were on wheelchairs, the efficient pilots with their smooth landing of the plane back and forth, cleanliness of the restrooms and other amenities provided to the passengers! Flights were on time it’s fine with a little bit delay but we arrived on time!

8.5
Very Good
1,124 reviews
8.5
Very Good
1,124 reviews

Boarding

8.6

Crew

8.8

Overall

8.5

Food

8.1

Comfort

8.3

Entertainment

8.2

Reviews

1 / 10

I like the crews’ services, especially for sr citizens who were on wheelchairs, the efficient pilots with their smooth landing of the plane back and forth, cleanliness of the restrooms and other amenities provided to the passengers! Flights were on time it’s fine with a little bit delay but we arrived on time!

8.5
Very Good
884 reviews
8.5
Very Good
1,124 reviews

Boarding

8.6

Crew

8.8

Overall

8.5

Food

8.1

Comfort

8.3

Entertainment

8.2

Reviews

1 / 10

I like the crews’ services, especially for sr citizens who were on wheelchairs, the efficient pilots with their smooth landing of the plane back and forth, cleanliness of the restrooms and other amenities provided to the passengers! Flights were on time it’s fine with a little bit delay but we arrived on time!

8.4
Very Good
1,476 reviews
8.5
Very Good
1,124 reviews

Boarding

8.6

Crew

8.8

Overall

8.5

Food

8.1

Comfort

8.3

Entertainment

8.2

Reviews

1 / 10

I like the crews’ services, especially for sr citizens who were on wheelchairs, the efficient pilots with their smooth landing of the plane back and forth, cleanliness of the restrooms and other amenities provided to the passengers! Flights were on time it’s fine with a little bit delay but we arrived on time!

8.3
Very Good
1,451 reviews
8.5
Very Good
1,124 reviews

Boarding

8.6

Crew

8.8

Overall

8.5

Food

8.1

Comfort

8.3

Entertainment

8.2

Reviews

1 / 10

I like the crews’ services, especially for sr citizens who were on wheelchairs, the efficient pilots with their smooth landing of the plane back and forth, cleanliness of the restrooms and other amenities provided to the passengers! Flights were on time it’s fine with a little bit delay but we arrived on time!

8.3
Very Good
1,405 reviews
8.5
Very Good
1,124 reviews

Boarding

8.6

Crew

8.8

Overall

8.5

Food

8.1

Comfort

8.3

Entertainment

8.2

Reviews

1 / 10

I like the crews’ services, especially for sr citizens who were on wheelchairs, the efficient pilots with their smooth landing of the plane back and forth, cleanliness of the restrooms and other amenities provided to the passengers! Flights were on time it’s fine with a little bit delay but we arrived on time!

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 is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago O'Hare Intl typically cost S$ 122, while return flights cost around S$ 212.

  • How much is a return flight to Chicago?

    A return flight to Chicago will typically cost around S$ 161, 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 20 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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