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S$ 63+ Cheap flights from 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 18-10. 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.
CHI — SIN
18 Oct — 25 Oct1
1 adult
1 adult, Economy

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 18 September 2025.

Good round-trip deal

S$ 254 or less

Good one-way deal

S$ 87 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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Find flights from Chicago

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 18 September 2025.

Thu 9-1008:45ORD - GRR
Nonstop1h 01mUnited Airlines
Mon 13-1018:39GRR - ORD
Nonstop1h 11mUnited Airlines
Deal found 16-9S$ 124
Tue 10-219:50ORD - GRR
Nonstop1h 10mUnited Airlines
Wed 11-216:51GRR - ORD
Nonstop1h 19mUnited Airlines
Deal found 14-9S$ 200
Wed 17-1206:45ORD - GRR
1 stop5h 29mDelta
Thu 18-1213:54GRR - ORD
1 stop3h 24mDelta
Deal found 16-9S$ 226
Tue 10-210:35ORD - GRR
1 stop3h 42mDelta
Wed 11-216:00GRR - ORD
1 stop5h 38mDelta
Deal found 14-9S$ 265
Sun 12-1010:35ORD - GRR
Nonstop1h 12mUnited Airlines
Thu 16-1006:00GRR - ORD
Nonstop1h 17mUnited Airlines
Deal found 17-9S$ 267
Fri 5-1214:09ORD - GRR
Nonstop0h 52mUnited Airlines
Sun 7-1207:30GRR - ORD
Nonstop1h 12mUnited Airlines
Deal found 16-9S$ 297
Wed 15-1007:10ORD - GRR
1 stop5h 16mDelta
Wed 22-1005:30GRR - ORD
1 stop3h 20mDelta
Deal found 17-9S$ 304
Wed 15-1016:00ORD - PWM
1 stop6h 59mUnited Airlines
Wed 22-1016:57PWM - ORD
Nonstop2h 51mUnited Airlines
Deal found 16-9S$ 308
Fri 17-1018:59ORD - GRR
1 stop3h 42mDelta
Fri 24-1014:06GRR - ORD
1 stop5h 08mDelta
Deal found 17-9S$ 313
Fri 10-1020:05ORD - GRR
Nonstop1h 08mUnited Airlines
Sun 12-1007:30GRR - ORD
Nonstop1h 11mUnited Airlines
Deal found 16-9S$ 314
Mon 9-211:00ORD - PWM
Nonstop2h 39mUnited Airlines
Wed 18-205:45PWM - ORD
Nonstop3h 12mUnited Airlines
Deal found 17-9S$ 318
Sat 18-1016:05ORD - PWM
1 stop6h 15mUnited Airlines
Sat 25-1019:25PWM - ORD
1 stop4h 50mUnited Airlines
Deal found 14-9S$ 320

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 18 September 2025. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Singapore

Route

Depart

Return

Price

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 13-10

08:45-10:46

Nonstop1h 01m

Grand Rapids Gerald R. Ford Intl

Mon 20-10

18:39-18:50

Nonstop1h 11m

S$ 124

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 10-2

19:50-22:00

Nonstop1h 10m

Grand Rapids Gerald R. Ford Intl

Wed 11-2

16:51-17:10

Nonstop1h 19m

S$ 200

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 10-2

06:00-10:53

1 stop3h 53m

Grand Rapids Gerald R. Ford Intl

Wed 11-2

16:00-20:38

1 stop5h 38m

S$ 226

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 17-12

06:45-13:14

1 stop5h 29m

Grand Rapids Gerald R. Ford Intl

Thu 18-12

13:54-16:18

1 stop3h 24m

S$ 226

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sun 12-10

10:35-12:47

Nonstop1h 12m

Grand Rapids Gerald R. Ford Intl

Thu 16-10

06:00-06:17

Nonstop1h 17m

S$ 267

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 5-12

14:09-16:01

Nonstop0h 52m

Grand Rapids Gerald R. Ford Intl

Sun 7-12

07:30-07:42

Nonstop1h 12m

S$ 297

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 15-10

07:10-13:26

1 stop5h 16m

Grand Rapids Gerald R. Ford Intl

Wed 22-10

05:30-07:50

1 stop3h 20m

S$ 304

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8-11

18:15-21:50

Nonstop2h 35m

Portland

Wed 12-11

06:00-11:46

1 stop6h 46m

S$ 308

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 10-10

20:05-22:13

Nonstop1h 08m

Grand Rapids Gerald R. Ford Intl

Sun 12-10

07:30-07:41

Nonstop1h 11m

S$ 314

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 12-11

06:45-12:08

1 stop4h 23m

Portland

Sat 15-11

14:30-20:29

2 stops6h 59m

S$ 327

Flights are sorted by cheapest return flights first.

Deals found on 14-9

Showing 1-10 of 60 results
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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 12 September 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 4 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$ 844). Flying from Chicago in June will prove the most costly (average of S$ 1,534). 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$ 713

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,680 flights per day), Detroit (1,254 flights per day) and Los Angeles (781 flights per day).

Krakow J. Paul II Balice
Krakow J. Paul II Balice
From S$ 772
Buffalo
Buffalo
From S$ 199
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 408
Amsterdam Schiphol
Amsterdam Schiphol
From S$ 1,146

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$ 59. Explore other affordable destinations below.

Pittsburgh
Pittsburgh
From S$ 46
Buffalo
Buffalo
From S$ 199
New York
New York
From S$ 213
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 408

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
3,965 reviews
Check prices

Overall

7.3

Boarding

7.3

Food

7.4

Comfort

7.3

Crew

7.7

Entertainment

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
3,965 reviews
Turkish Airlines
7.3
Good
3,965 reviews
Check prices

Overall

7.3

Boarding

7.3

Food

7.4

Comfort

7.3

Crew

7.7

Entertainment

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 18 September 2025.

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

    This month, the top selected destinations from Chicago are Athens, Boston, Atlanta. Throughout the year, Atlanta, Boston, Ahmedabad 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$ 884 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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