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Cheap flights to Chicago

WAS — CHI
24 Mar — 31 Mar1
1 adult
Sun 24-3
Sun 31-3

Find deals on flights to Chicago by searching across hundreds of travel sites at once.

 
Cheapflights users frequently choose these airlines when searching for flights to Chicago, based on our search results.
Cheapflights users frequently choose these airlines when searching for flights to Chicago, based on our search 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 203,602 searches and data was last updated on 19 March 2024.

Popular in

August

Cheapest in

October

Average price

S$ 1,871

Return from

S$ 1,226

One-way from

S$ 823
High demand for flights, 8% potential price rise
Best time to find cheap flights, 2% potential price drop
Average for return flights in March 2024
From Singapore Changi to Chicago
One-way flight from Singapore Changi (SIN) to Chicago

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$ 0 while a return flight costs S$ 0. Price data was last updated on 17 March 2024.

Currently, January is the cheapest month in which you can book a flight to Chicago (average of S$ 0). Flying to Chicago in May will prove the most costly (average of S$ 1,226). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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.
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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 17 March 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 Sunday mornings, when prices are usually at their highest.
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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 19 March 2024.
Read through reviews of airlines servicing Chicago, such as Japan Airlines, Cathay Pacific 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.
8.6
Very Good
1,244 reviews

Overall

8.6

Comfort

8.4

Crew

8.8

Entertainment

8.2

Boarding

8.6

Food

8.2

Reviews

1 / 10

I went to airport at 8;30 pm really to check in but they didn’t let me go they said my ticket had problems …I confused asked them check out to office help me please but they said they can’t ! beg them help😭They told me if want to fly now need buy another ticket $ 3585 or want go tomorrow $1889 OMG it’s terrible I cried and asked them could you help me find another ticket cheaper I need to go back home on time he stand up said NO if you want cheap go buy another plane ✈️ I did ! I bought ticket of American Airlines is $980 ! I came home now ! Please 🙏 check out about my problems it’s terrible for travelers! I am so tired and very disappointed ! Own business in USA 🇺🇸 I understand how to take care of customer services it’s very important ! Please 🙏 check out on them be fair for customer satisfaction ! By that time I spoke with them Vietnamese language and English too but they try to making money 💴 from me it’s very poor! So sad 😭 for vacation! Please 🙏

8.6
Very Good
1,244 reviews
8.6
Very Good
1,244 reviews

Overall

8.6

Comfort

8.4

Crew

8.8

Entertainment

8.2

Boarding

8.6

Food

8.2

Reviews

1 / 10

I went to airport at 8;30 pm really to check in but they didn’t let me go they said my ticket had problems …I confused asked them check out to office help me please but they said they can’t ! beg them help😭They told me if want to fly now need buy another ticket $ 3585 or want go tomorrow $1889 OMG it’s terrible I cried and asked them could you help me find another ticket cheaper I need to go back home on time he stand up said NO if you want cheap go buy another plane ✈️ I did ! I bought ticket of American Airlines is $980 ! I came home now ! Please 🙏 check out about my problems it’s terrible for travelers! I am so tired and very disappointed ! Own business in USA 🇺🇸 I understand how to take care of customer services it’s very important ! Please 🙏 check out on them be fair for customer satisfaction ! By that time I spoke with them Vietnamese language and English too but they try to making money 💴 from me it’s very poor! So sad 😭 for vacation! Please 🙏

8.5
Very Good
1,005 reviews
8.6
Very Good
1,244 reviews

Overall

8.6

Comfort

8.4

Crew

8.8

Entertainment

8.2

Boarding

8.6

Food

8.2

Reviews

1 / 10

I went to airport at 8;30 pm really to check in but they didn’t let me go they said my ticket had problems …I confused asked them check out to office help me please but they said they can’t ! beg them help😭They told me if want to fly now need buy another ticket $ 3585 or want go tomorrow $1889 OMG it’s terrible I cried and asked them could you help me find another ticket cheaper I need to go back home on time he stand up said NO if you want cheap go buy another plane ✈️ I did ! I bought ticket of American Airlines is $980 ! I came home now ! Please 🙏 check out about my problems it’s terrible for travelers! I am so tired and very disappointed ! Own business in USA 🇺🇸 I understand how to take care of customer services it’s very important ! Please 🙏 check out on them be fair for customer satisfaction ! By that time I spoke with them Vietnamese language and English too but they try to making money 💴 from me it’s very poor! So sad 😭 for vacation! Please 🙏

8.4
Very Good
1,477 reviews
8.6
Very Good
1,244 reviews

Overall

8.6

Comfort

8.4

Crew

8.8

Entertainment

8.2

Boarding

8.6

Food

8.2

Reviews

1 / 10

I went to airport at 8;30 pm really to check in but they didn’t let me go they said my ticket had problems …I confused asked them check out to office help me please but they said they can’t ! beg them help😭They told me if want to fly now need buy another ticket $ 3585 or want go tomorrow $1889 OMG it’s terrible I cried and asked them could you help me find another ticket cheaper I need to go back home on time he stand up said NO if you want cheap go buy another plane ✈️ I did ! I bought ticket of American Airlines is $980 ! I came home now ! Please 🙏 check out about my problems it’s terrible for travelers! I am so tired and very disappointed ! Own business in USA 🇺🇸 I understand how to take care of customer services it’s very important ! Please 🙏 check out on them be fair for customer satisfaction ! By that time I spoke with them Vietnamese language and English too but they try to making money 💴 from me it’s very poor! So sad 😭 for vacation! Please 🙏

8.4
Very Good
1,636 reviews
8.6
Very Good
1,244 reviews

Overall

8.6

Comfort

8.4

Crew

8.8

Entertainment

8.2

Boarding

8.6

Food

8.2

Reviews

1 / 10

I went to airport at 8;30 pm really to check in but they didn’t let me go they said my ticket had problems …I confused asked them check out to office help me please but they said they can’t ! beg them help😭They told me if want to fly now need buy another ticket $ 3585 or want go tomorrow $1889 OMG it’s terrible I cried and asked them could you help me find another ticket cheaper I need to go back home on time he stand up said NO if you want cheap go buy another plane ✈️ I did ! I bought ticket of American Airlines is $980 ! I came home now ! Please 🙏 check out about my problems it’s terrible for travelers! I am so tired and very disappointed ! Own business in USA 🇺🇸 I understand how to take care of customer services it’s very important ! Please 🙏 check out on them be fair for customer satisfaction ! By that time I spoke with them Vietnamese language and English too but they try to making money 💴 from me it’s very poor! So sad 😭 for vacation! Please 🙏

8.3
Very Good
1,520 reviews
8.6
Very Good
1,244 reviews

Overall

8.6

Comfort

8.4

Crew

8.8

Entertainment

8.2

Boarding

8.6

Food

8.2

Reviews

1 / 10

I went to airport at 8;30 pm really to check in but they didn’t let me go they said my ticket had problems …I confused asked them check out to office help me please but they said they can’t ! beg them help😭They told me if want to fly now need buy another ticket $ 3585 or want go tomorrow $1889 OMG it’s terrible I cried and asked them could you help me find another ticket cheaper I need to go back home on time he stand up said NO if you want cheap go buy another plane ✈️ I did ! I bought ticket of American Airlines is $980 ! I came home now ! Please 🙏 check out about my problems it’s terrible for travelers! I am so tired and very disappointed ! Own business in USA 🇺🇸 I understand how to take care of customer services it’s very important ! Please 🙏 check out on them be fair for customer satisfaction ! By that time I spoke with them Vietnamese language and English too but they try to making money 💴 from me it’s very poor! So sad 😭 for vacation! Please 🙏

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.

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