Find flights
Airlines

S$ 126+ 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 6-5. 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
20 Apr — 27 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 15 April 2025.

Good round-trip deal

S$ 262 or less

Good one-way deal

S$ 156 or less
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

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 15 April 2025.

Mon 5-521:20ORD - GRR
Nonstop1h 08mUnited Airlines
Tue 6-507:15GRR - ORD
Nonstop1h 07mUnited Airlines
Deal found 14-4S$ 128
Tue 6-510:30ORD - GRR
1 stop3h 24mDelta
Wed 7-515:34GRR - ORD
1 stop4h 03mDelta
Deal found 14-4S$ 233
Tue 3-609:00ORD - PWM
1 stop7h 43mUnited Airlines
Wed 11-606:00PWM - ORD
Nonstop2h 53mUnited Airlines
Deal found 14-4S$ 312
Wed 2-717:59ORD - PWM
1 stop5h 27mDelta
Thu 3-718:56PWM - ORD
1 stop6h 03mDelta
Deal found 14-4S$ 314
Tue 27-505:00ORD - GRR
1 stop5h 08mAmerican Airlines
Tue 27-519:33GRR - ORD
Nonstop1h 17mAmerican Airlines
Deal found 14-4S$ 314
Tue 19-820:42ORD - ONT
1 stop16h 03mAlaska Airlines
Sun 24-807:10ONT - ORD
1 stop19h 54mAlaska Airlines
Deal found 14-4S$ 324
Fri 2-506:20ORD - PWM
1 stop7h 05mJetBlue
Mon 5-515:20PWM - ORD
1 stop8h 02mJetBlue
Deal found 14-4S$ 329
Fri 1-812:40ORD - ONT
1 stop10h 10mSouthwest
Thu 7-812:55ONT - ORD
1 stop7h 25mSouthwest
Deal found 14-4S$ 332
Fri 27-619:20ORD - ONT
1 stop6h 26mDelta
Sat 5-713:15ONT - ORD
1 stop6h 54mDelta
Deal found 14-4S$ 338
Sun 1-619:55ORD - ONT
Nonstop4h 31mUnited Airlines
Sat 7-607:00ONT - ORD
Nonstop3h 58mUnited Airlines
Deal found 14-4S$ 347
Thu 18-906:24ORD - ONT
1 stop9h 42mHawaiian Airlines
Sun 28-919:17ONT - ORD
1 stop8h 23mHawaiian Airlines
Deal found 14-4S$ 376
Fri 27-613:50ORD - PWM
1 stop9h 15mSouthwest
Tue 1-705:30PWM - ORD
2 stops10h 30mSouthwest
Deal found 13-4S$ 388

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 15 April 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 6-5

10:30-14:54

1 stop3h 24m

Grand Rapids Gerald R. Ford Intl

Wed 7-5

15:34-18:37

1 stop4h 03m

S$ 233

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sun 11-5

18:15-20:18

Nonstop1h 03m

Grand Rapids Gerald R. Ford Intl

Thu 15-5

07:15-07:22

Nonstop1h 07m

S$ 275

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 3-6

09:00-17:43

1 stop7h 43m

Portland

Wed 11-6

06:00-07:53

Nonstop2h 53m

S$ 312

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 27-5

05:00-11:08

1 stop5h 08m

Grand Rapids Gerald R. Ford Intl

Tue 27-5

19:33-19:50

Nonstop1h 17m

S$ 314

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 2-7

15:40-00:26

1 stop7h 46m

Portland

Wed 9-7

11:59-19:43

1 stop8h 44m

S$ 314

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Tue 19-8

20:42-10:45

1 stop16h 03m

Ontario

Sun 24-8

07:10-05:04

1 stop19h 54m

S$ 324

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 2-5

06:20-14:25

1 stop7h 05m

Portland

Mon 5-5

15:20-22:22

1 stop8h 02m

S$ 329

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Fri 1-8

12:40-20:50

1 stop10h 10m

Ontario

Thu 7-8

12:55-22:20

1 stop7h 25m

S$ 332

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Fri 27-6

19:20-23:46

1 stop6h 26m

Ontario

Sat 5-7

13:15-22:09

1 stop6h 54m

S$ 338

ChicagoOntario

ORD - ONT

ORDONT

Chicago O'Hare Intl

Sun 1-6

19:55-22:26

Nonstop4h 31m

Ontario

Sat 7-6

07:00-12:58

Nonstop3h 58m

S$ 347

Flights are sorted by cheapest return flights first.

Deals found on 14-4

Showing 1-10 of 60 results
1
2
3
...
6

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 11 April 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$ 958). Flying from Chicago in June will prove the most costly (average of S$ 1,577). 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 (1,330 flights per day), Detroit (972 flights per day) and Los Angeles (656 flights per day).

San Francisco

San Francisco

From S$ 107

Rome

Rome

From S$ 719

Buffalo

Buffalo

From S$ 199

Phoenix Sky Harbor Intl

Phoenix Sky Harbor Intl

From S$ 256

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$ 141. Explore other affordable destinations below.

San Francisco

San Francisco

From S$ 107

Buffalo

Buffalo

From S$ 199

Phoenix Sky Harbor Intl

Phoenix Sky Harbor Intl

From S$ 256

Rome

Rome

From S$ 719

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
1,176 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

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
1,176 reviews
EVA Air
8.4
Very Good
1,176 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

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
1,063 reviews
EVA Air
8.4
Very Good
1,176 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

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
1,176 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

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
841 reviews
EVA Air
8.4
Very Good
1,176 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

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
3,195 reviews
EVA Air
8.4
Very Good
1,176 reviews
Check prices

Overall

8.4

Comfort

8.3

Crew

8.6

Entertainment

8.0

Food

8.1

Boarding

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.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from Los Angeles
Direct flights from San Francisco
Direct flights from Honolulu
Direct flights from Seattle
Direct flights from Las Vegas
Direct flights from Boston
Direct flights from Miami
Direct flights from Orlando
Direct flights from Atlanta
Direct flights from Denver
Direct flights from Austin
Direct flights from San Diego
Direct flights from Philadelphia
Direct flights from Portland
Direct flights from Minneapolis
Direct flights from Anchorage
Direct flights from Charlotte
Direct flights from Pittsburgh
Direct flights from New Orleans
Direct flights from Tampa
Direct flights from Nashville
Direct flights from Cleveland
Direct flights from Indianapolis
Direct flights from Salt Lake City
Direct flights from Fort Lauderdale
Direct flights from San Antonio
Direct flights from Buffalo
Direct flights from Fairbanks
Direct flights from Wichita
Direct flights from Boise

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 April 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, 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$ 1,076 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.

See more FAQs

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights