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S$ 120+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11-8. 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
2 Jul — 9 Jul1
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 27 June 2025.

Good round-trip deal

S$ 254 or less

Good one-way deal

S$ 203 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 27 June 2025.

Mon 11-821:50ORD - GRR
Nonstop1h 05mUnited Airlines
Sat 16-818:34GRR - ORD
Nonstop1h 21mUnited Airlines
Deal found 25-6S$ 120
Fri 8-819:01ORD - GRR
1 stop3h 45mDelta
Sun 17-805:30GRR - ORD
1 stop3h 34mDelta
Deal found 26-6S$ 226
Wed 13-806:15ORD - PWM
1 stop6h 08mJetBlue
Mon 18-806:10PWM - ORD
1 stop5h 37mJetBlue
Deal found 24-6S$ 297
Sun 31-805:45ORD - PWM
1 stop5h 44mDelta
Sat 6-907:00PWM - ORD
1 stop7h 09mDelta
Deal found 23-6S$ 311
Wed 13-818:30ORD - PWM
Nonstop2h 31mUnited Airlines
Thu 14-818:20PWM - ORD
Nonstop3h 05mUnited Airlines
Deal found 25-6S$ 312
Tue 12-806:00ORD - ONT
1 stop10h 46mAlaska Airlines
Tue 9-911:39ONT - ORD
1 stop10h 20mAlaska Airlines
Deal found 25-6S$ 356
Tue 26-813:30ORD - ONT
1 stop7h 41mDelta
Sat 30-809:50ONT - ORD
2 stops12h 06mDelta
Deal found 24-6S$ 362
Sat 19-718:15ORD - PWM
1 stop16h 30mSun Country Air
Sat 26-712:34PWM - ORD
1 stop5h 53mSun Country Air
Deal found 26-6S$ 363
Thu 18-913:50ORD - PWM
1 stop5h 10mSouthwest
Sat 20-905:45PWM - ORD
2 stops11h 40mSouthwest
Deal found 24-6S$ 380
Tue 29-713:50ORD - GRR
1 stop7h 10mSouthwest
Thu 31-705:40GRR - ORD
1 stop8h 25mSouthwest
Deal found 26-6S$ 395
Sat 19-714:35ORD - ONT
1 stop8h 19mUnited Airlines
Sat 2-807:00ONT - ORD
Nonstop4h 02mUnited Airlines
Deal found 25-6S$ 519
Sat 19-718:55ORD - ONT
1 stop6h 05mSouthwest
Sat 2-809:25ONT - ORD
2 stops11h 40mSouthwest
Deal found 25-6S$ 538

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 27 June 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

Thu 24-7

15:35-17:41

Nonstop1h 06m

Grand Rapids Gerald R. Ford Intl

Thu 31-7

07:30-07:38

Nonstop1h 08m

S$ 288

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 13-8

06:15-13:23

1 stop6h 08m

Portland

Mon 18-8

06:10-10:47

1 stop5h 37m

S$ 297

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 29-8

09:10-13:19

1 stop3h 09m

Grand Rapids Gerald R. Ford Intl

Fri 29-8

18:05-20:23

1 stop3h 18m

S$ 297

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 31-8

05:45-12:29

1 stop5h 44m

Portland

Sat 6-9

07:00-13:09

1 stop7h 09m

S$ 311

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 13-8

18:30-22:01

Nonstop2h 31m

Portland

Thu 14-8

18:20-20:25

Nonstop3h 05m

S$ 312

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 12-8

06:00-14:46

1 stop10h 46m

Ontario

Tue 9-9

11:39-23:59

1 stop10h 20m

S$ 356

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 26-8

13:30-19:11

1 stop7h 41m

Ontario

Sat 30-8

09:50-23:56

2 stops12h 06m

S$ 362

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 19-7

18:15-11:45

1 stop16h 30m

Portland

Sat 26-7

12:34-17:27

1 stop5h 53m

S$ 363

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 18-9

13:50-20:00

1 stop5h 10m

Portland

Sat 20-9

05:45-16:25

2 stops11h 40m

S$ 380

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 29-7

13:50-22:00

1 stop7h 10m

Grand Rapids Gerald R. Ford Intl

Thu 31-7

05:40-13:05

1 stop8h 25m

S$ 395

Flights are sorted by cheapest return flights first.

Deals found on 26-6

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 20 June 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, March is the cheapest month in which you can book a flight from Chicago (average of S$ 924). Flying from Chicago in June will prove the most costly (average of S$ 1,557). 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 (1,239 flights per day), Detroit (1,052 flights per day) and Los Angeles (645 flights per day).

Buffalo
Buffalo
From S$ 199
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 376
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 San Francisco, with prices starting at S$ 203. Explore other affordable destinations below.

San Francisco
San Francisco
From S$ 159
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 EVA Air, Korean Air, andJapan Airlines from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
EVA Air
8.4
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
EVA Air
8.4
Very Good
1,208 reviews
EVA Air
8.4
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
Korean Air
8.4
Very Good
1,099 reviews
EVA Air
8.4
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
Japan Airlines
8.3
Very Good
1,504 reviews
EVA Air
8.4
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
China Airlines
8.3
Very Good
745 reviews
EVA Air
8.4
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount
ANA
8.3
Very Good
887 reviews
EVA Air
8.4
Very Good
1,208 reviews
Check prices

Entertainment

8.0

Boarding

8.4

Crew

8.6

Overall

8.4

Comfort

8.3

Food

8.1

Reviews

1 / 20
10.0
Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

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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 27 June 2025.

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

    This month, the top selected destinations from Chicago are Athens, Boston, Amman. 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 March. 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$ 853 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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