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S$ 137+ 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 1-7. 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
19 May — 26 May1
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 14 May 2025.

Good round-trip deal

S$ 259 or less

Good one-way deal

S$ 155 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 14 May 2025.

Tue 1-707:05ORD - GRR
1 stop5h 20mDelta
Tue 1-717:45GRR - ORD
1 stop3h 42mDelta
Deal found 14-5S$ 288
Tue 10-621:10ORD - GRR
Nonstop1h 05mUnited Airlines
Tue 17-607:30GRR - ORD
Nonstop1h 08mUnited Airlines
Deal found 13-5S$ 293
Thu 17-719:35ORD - ONT
Nonstop4h 31mUnited Airlines
Thu 31-707:00ONT - ORD
Nonstop4h 03mUnited Airlines
Deal found 13-5S$ 296
Thu 18-915:00ORD - PWM
1 stop7h 01mUnited Airlines
Mon 22-918:23PWM - ORD
Nonstop3h 00mUnited Airlines
Deal found 13-5S$ 308
Mon 14-706:00ORD - PWM
1 stop6h 23mJetBlue
Fri 18-714:20PWM - ORD
1 stop9h 08mJetBlue
Deal found 14-5S$ 309
Sat 31-516:25ORD - PWM
1 stop6h 34mDelta
Sat 7-606:05PWM - ORD
2 stops11h 42mDelta
Deal found 14-5S$ 310
Fri 27-613:50ORD - PWM
1 stop9h 15mSouthwest
Mon 30-605:40PWM - ORD
1 stop8h 25mSouthwest
Deal found 14-5S$ 313
Thu 18-906:20ORD - ONT
1 stop9h 49mAlaska Airlines
Mon 22-919:22ONT - ORD
1 stop9h 41mAlaska Airlines
Deal found 13-5S$ 321
Fri 8-807:00ORD - ONT
2 stops7h 40mSouthwest
Sun 10-805:10ONT - ORD
1 stop8h 10mSouthwest
Deal found 13-5S$ 328
Fri 27-619:20ORD - ONT
1 stop6h 26mDelta
Sat 5-713:15ONT - ORD
1 stop6h 54mDelta
Deal found 14-5S$ 335
Thu 25-906:20ORD - ONT
1 stop9h 49mHawaiian Airlines
Mon 6-1019:25ONT - ORD
1 stop8h 56mHawaiian Airlines
Deal found 13-5S$ 373
Fri 20-618:17ORD - PWM
1 stop16h 40mSun Country Air
Sun 22-612:46PWM - ORD
1 stop7h 13mSun Country Air
Deal found 14-5S$ 558

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 14 May 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

Tue 1-7

07:05-13:25

1 stop5h 20m

Grand Rapids Gerald R. Ford Intl

Tue 1-7

17:45-20:27

1 stop3h 42m

S$ 288

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 10-6

21:10-23:15

Nonstop1h 05m

Grand Rapids Gerald R. Ford Intl

Tue 17-6

07:30-07:38

Nonstop1h 08m

S$ 293

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Thu 17-7

19:35-22:06

Nonstop4h 31m

Ontario

Thu 31-7

07:00-13:03

Nonstop4h 03m

S$ 296

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 18-9

15:00-23:01

1 stop7h 01m

Portland

Mon 22-9

18:23-20:23

Nonstop3h 00m

S$ 308

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 14-7

06:00-13:23

1 stop6h 23m

Portland

Fri 18-7

14:20-22:28

1 stop9h 08m

S$ 309

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 31-5

16:25-23:59

1 stop6h 34m

Portland

Sat 7-6

06:05-16:47

2 stops11h 42m

S$ 310

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 27-6

13:50-00:05

1 stop9h 15m

Portland

Mon 30-6

05:40-13:05

1 stop8h 25m

S$ 313

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Thu 18-9

06:20-14:09

1 stop9h 49m

Ontario

Mon 22-9

19:22-07:03

1 stop9h 41m

S$ 321

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Fri 8-8

07:00-12:40

2 stops7h 40m

Ontario

Sun 10-8

05:10-15:20

1 stop8h 10m

S$ 328

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Fri 27-6

19:20-23:46

1 stop6h 26m

Ontario

Wed 9-7

13:15-22:08

1 stop6h 53m

S$ 335

Flights are sorted by cheapest return flights first.

Deals found on 13-5

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 9 May 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$ 950). Flying from Chicago in June will prove the most costly (average of S$ 1,561). 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 (1,765 flights per day), Detroit (1,262 flights per day) and Los Angeles (773 flights per day).

San Francisco
San Francisco
From S$ 107
Rome
Rome
From S$ 719
Buffalo
Buffalo
From S$ 199
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$ 140. Explore other affordable destinations below.

San Francisco
San Francisco
From S$ 107
Buffalo
Buffalo
From S$ 199
Rome
Rome
From S$ 719
Amsterdam Schiphol
Amsterdam Schiphol
From S$ 1,146

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.
EVA Air
8.4
Very Good
1,192 reviews
Check prices

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Crew

8.6

Overall

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.
EVA Air
8.4
Very Good
1,192 reviews
EVA Air
8.4
Very Good
1,192 reviews
Check prices

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Crew

8.6

Overall

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.
Korean Air
8.4
Very Good
1,073 reviews
EVA Air
8.4
Very Good
1,192 reviews
Check prices

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Crew

8.6

Overall

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.
Japan Airlines
8.3
Very Good
1,471 reviews
EVA Air
8.4
Very Good
1,192 reviews
Check prices

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Crew

8.6

Overall

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.
ANA
8.3
Very Good
864 reviews
EVA Air
8.4
Very Good
1,192 reviews
Check prices

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Crew

8.6

Overall

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.
Delta
8.0
Very Good
7,946 reviews
EVA Air
8.4
Very Good
1,192 reviews
Check prices

Comfort

8.3

Boarding

8.4

Entertainment

8.0

Crew

8.6

Overall

8.4

Food

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

TPE - SEA

The flight and crew were exceptional as always when I fly with EVA.

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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 14 May 2025.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, 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 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$ 1,067 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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