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Cheap flights from Chicago to anywhere

CHI — SIN
20 Aug — 27 Aug1
1 adult

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 15 August 2025.

Good round-trip deal

S$ 255 or less

Good one-way deal

S$ 88 or less
Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from 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 from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a return flight from Chicago to Singapore. Price data was last updated on 8 August 2025.

The price you pay for your flight from Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago?

Currently, September is the cheapest month in which you can book a flight from Chicago (average of S$ 897). Flying from Chicago in June will prove the most costly (average of S$ 1,545). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

When flying from Chicago check dates and pricing for the following: United Airlines. As it departs for the following popular destinations: Singapore.

United Airlines
United Airlines
From S$ 836

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,524 flights per day), Detroit (1,096 flights per day) and Los Angeles (739 flights per day).

Hong Kong Intl
Hong Kong Intl
From S$ 789
New York
New York
From S$ 108
Buffalo
Buffalo
From S$ 199
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 376

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Pittsburgh, with prices starting at S$ 60. Explore other affordable destinations below.

Pittsburgh
Pittsburgh
From S$ 46
New York
New York
From S$ 108
Buffalo
Buffalo
From S$ 199
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 376

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 200,618 searches.
Read reviews from past customers who have flown Turkish Airlines from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Turkish Airlines
7.3
Good
3,939 reviews
Check prices

Crew

7.7

Overall

7.3

Boarding

7.3

Entertainment

7.4

Comfort

7.3

Food

7.4

Reviews

1 / 20
2.0
Mediocre

Brian,Jul 2025

SEA - IST

Horrible check-in experience in Seattle. Was actually yelled at by a customer service rep and then he intentionally would put us in the back row to make sure our seats would not recline. When I complained to customer service they told me they did not find any issues with how we were treated. The sinks did not drain in the bathroom during the flight and my in-flight entertainment never worked during a 12 hour flight. They said they would reset 3 times but never did. Would never fly them again.
Turkish Airlines
7.3
Good
3,939 reviews
Turkish Airlines
7.3
Good
3,939 reviews
Check prices

Crew

7.7

Overall

7.3

Boarding

7.3

Entertainment

7.4

Comfort

7.3

Food

7.4

Reviews

1 / 20
2.0
Mediocre

Brian,Jul 2025

SEA - IST

Horrible check-in experience in Seattle. Was actually yelled at by a customer service rep and then he intentionally would put us in the back row to make sure our seats would not recline. When I complained to customer service they told me they did not find any issues with how we were treated. The sinks did not drain in the bathroom during the flight and my in-flight entertainment never worked during a 12 hour flight. They said they would reset 3 times but never did. Would never fly them again.

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 15 August 2025.

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Boston, Atlanta, Athens. Throughout the year, Atlanta, Boston, Mumbai are some of the top choices made by users flying from Chicago.

  • What is the cheapest month to fly from Chicago?

    Currently, the cheapest month for flights from Chicago is September. The most expensive month for flights is June. The cheapest prices are shown above but prices will vary according to departure times, airlines, class and how early you book.

  • Where are the cheapest places to fly to from Chicago?

    View the cheapest flight destinations from Chicago:
    Fly from Chicago to Singapore from S$ 785 round trip

  • How does Cheapflights help users find flights from Chicago?

    When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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How does Cheapflights help users find flights from Chicago?

When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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