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S$ 130+ 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 8-5. 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
30 Mar — 6 Apr1
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 25 March 2025.

Good round-trip deal

S$ 266 or less

Good one-way deal

S$ 159 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 25 March 2025.

Thu 8-521:20ORD - GRR
Nonstop1h 08mUnited Airlines
Thu 15-507:15GRR - ORD
Nonstop1h 07mUnited Airlines
Deal found 24-3S$ 130
Tue 6-509:30ORD - GRR
1 stop4h 24mDelta
Wed 7-515:34GRR - ORD
1 stop4h 03mDelta
Deal found 24-3S$ 237
Tue 15-418:35ORD - PWM
1 stop5h 07mDelta
Fri 25-407:00PWM - ORD
1 stop6h 39mDelta
Deal found 24-3S$ 298
Sat 24-519:55ORD - ONT
Nonstop4h 31mUnited Airlines
Sun 1-607:00ONT - ORD
Nonstop4h 03mUnited Airlines
Deal found 24-3S$ 304
Tue 8-418:12ORD - PWM
Nonstop2h 23mUnited Airlines
Wed 9-416:15PWM - ORD
Nonstop3h 00mUnited Airlines
Deal found 24-3S$ 306
Wed 11-616:03ORD - PWM
1 stop4h 54mJetBlue
Mon 16-606:10PWM - ORD
1 stop5h 37mJetBlue
Deal found 24-3S$ 310
Wed 23-409:00ORD - ONT
1 stop8h 32mAlaska Airlines
Tue 29-406:00ONT - ORD
1 stop9h 00mAlaska Airlines
Deal found 24-3S$ 329
Wed 23-418:55ORD - ONT
1 stop6h 05mSouthwest
Wed 30-415:40ONT - ORD
1 stop6h 00mSouthwest
Deal found 24-3S$ 330
Wed 23-407:25ORD - ONT
1 stop6h 51mDelta
Thu 1-517:15ONT - ORD
1 stop5h 38mDelta
Deal found 24-3S$ 344
Fri 6-613:50ORD - PWM
1 stop4h 15mSouthwest
Fri 13-605:40PWM - ORD
2 stops10h 20mSouthwest
Deal found 24-3S$ 407
Sun 6-720:10ORD - PWM
1 stop14h 25mSun Country Air
Fri 11-712:32PWM - ORD
1 stop7h 39mSun Country Air
Deal found 24-3S$ 508
Mon 12-519:15ORD - ATH
2 stops18h 05mScandinavian Airlines
Wed 21-507:50ATH - ORD
2 stops21h 43mScandinavian Airlines
Deal found 24-3S$ 775

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 25 March 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

Fri 9-5

21:20-23:28

Nonstop1h 08m

Grand Rapids Gerald R. Ford Intl

Fri 16-5

07:15-07:22

Nonstop1h 07m

S$ 290

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 15-4

18:35-00:42

1 stop5h 07m

Portland

Fri 25-4

07:00-12:39

1 stop6h 39m

S$ 298

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Sat 24-5

19:55-22:26

Nonstop4h 31m

Ontario

Sun 1-6

07:00-13:03

Nonstop4h 03m

S$ 304

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 8-4

18:12-21:35

Nonstop2h 23m

Portland

Wed 9-4

16:15-18:15

Nonstop3h 00m

S$ 306

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11-6

16:03-21:57

1 stop4h 54m

Portland

Mon 16-6

06:10-10:47

1 stop5h 37m

S$ 310

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 23-4

09:00-15:32

1 stop8h 32m

Ontario

Tue 29-4

06:00-17:00

1 stop9h 00m

S$ 329

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 23-4

18:55-23:00

1 stop6h 05m

Ontario

Wed 30-4

15:40-23:40

1 stop6h 00m

S$ 330

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Wed 23-4

07:25-12:16

1 stop6h 51m

Ontario

Thu 1-5

17:15-00:53

1 stop5h 38m

S$ 344

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Thu 17-4

06:35-11:27

1 stop3h 52m

Grand Rapids Gerald R. Ford Intl

Mon 21-4

18:31-07:55

1 stop14h 24m

S$ 349

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 6-6

13:50-19:05

1 stop4h 15m

Portland

Fri 13-6

05:40-15:00

2 stops10h 20m

S$ 407

Flights are sorted by cheapest return flights first.

Deals found on 24-3

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 21 March 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, February is the cheapest month in which you can book a flight from Chicago (average of S$ 995). Flying from Chicago in June will prove the most costly (average of S$ 1,608). 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 (1,234 flights per day), Detroit (904 flights per day) and Los Angeles (493 flights per day).

San Francisco

San Francisco

From S$ 107

Rome

Rome

From S$ 719

Atlanta Hartsfield-Jackson

Atlanta Hartsfield-Jackson

From S$ 2,310

Buffalo

Buffalo

From S$ 199

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$ 144. 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
1,171 reviews
Check prices

Food

8.1

Boarding

8.4

Crew

8.6

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.
EVA Air
8.4
Very Good
1,171 reviews
EVA Air
8.4
Very Good
1,171 reviews
Check prices

Food

8.1

Boarding

8.4

Crew

8.6

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.
Korean Air
8.4
Very Good
1,047 reviews
EVA Air
8.4
Very Good
1,171 reviews
Check prices

Food

8.1

Boarding

8.4

Crew

8.6

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.
Japan Airlines
8.3
Very Good
1,440 reviews
EVA Air
8.4
Very Good
1,171 reviews
Check prices

Food

8.1

Boarding

8.4

Crew

8.6

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.
ANA
8.3
Very Good
826 reviews
EVA Air
8.4
Very Good
1,171 reviews
Check prices

Food

8.1

Boarding

8.4

Crew

8.6

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.
Emirates
8.0
Very Good
3,190 reviews
EVA Air
8.4
Very Good
1,171 reviews
Check prices

Food

8.1

Boarding

8.4

Crew

8.6

Entertainment

8.0

Comfort

8.3

Overall

8.4

Reviews

1 / 20
6.0
Good

Anonymous,Feb 2025

SFO - TPE

Inside plane was clean and chair was comfortable, but flight attendants serving coffee without giving me cream and sugar, even I ask he escape my request.

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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 25 March 2025.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Barcelona-El Prat Airport. Throughout the year, Atlanta, Boston, Athens 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 February. 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$ 1,137 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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