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S$ 119+ 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 20-1. 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 Jan — 6 Feb1
1 adult
1 adult, Economy, 0 bags

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 31 December 2025.

Good round-trip deal

S$ 358 or less

Good one-way deal

S$ 56 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

Enter your travel dates to find the best prices.

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 31 December 2025.

Wed 28-111:00ORD - PWM
Nonstop2h 39mUnited Airlines
Wed 4-216:10PWM - ORD
Nonstop3h 08mUnited Airlines
Deal found 29-12S$ 268
Tue 10-309:50ORD - GRR
1 stop2h 51mDelta
Wed 11-308:10GRR - ORD
1 stop6h 07mDelta
Deal found 30-12S$ 271
Tue 20-111:00ORD - PWM
Nonstop2h 39mUnited Airlines
Wed 21-116:10PWM - ORD
Nonstop3h 08mUnited Airlines
Deal found 31-12S$ 283
Wed 28-108:45ORD - PWM
1 stop4h 46mUnited Airlines
Sat 31-106:00PWM - ORD
1 stop7h 05mUnited Airlines
Deal found 29-12S$ 294
Tue 20-107:00ORD - PWM
1 stop5h 45mDelta
Thu 22-112:43PWM - ORD
2 stops9h 22mDelta
Deal found 31-12S$ 300
Sat 14-215:21ORD - PWM
2 stops7h 57mDelta
Wed 18-214:35PWM - ORD
2 stops10h 21mDelta
Deal found 30-12S$ 307
Sat 17-106:50ORD - GRR
1 stop5h 35mDelta
Sun 18-108:15GRR - ORD
1 stop5h 53mDelta
Deal found 29-12S$ 309
Sat 14-207:00ORD - PWM
1 stop5h 43mDelta
Thu 19-206:00PWM - ORD
2 stops8h 34mDelta
Deal found 30-12S$ 313
Thu 30-406:00ORD - PWM
1 stop6h 38mUnited Airlines
Sun 3-509:37PWM - ORD
Nonstop2h 57mUnited Airlines
Deal found 29-12S$ 315
Sat 28-309:50ORD - PWM
1 stop5h 16mDelta
Fri 3-416:48PWM - ORD
1 stop4h 26mDelta
Deal found 30-12S$ 320
Wed 1-413:57ORD - PWM
2 stops8h 15mDelta
Sat 4-416:48PWM - ORD
1 stop4h 26mDelta
Deal found 29-12S$ 326
Wed 15-413:26ORD - GRR
1 stop4h 43mDelta
Sat 18-412:10GRR - ORD
1 stop5h 08mDelta
Deal found 29-12S$ 330

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 31 December 2025. In the last 7 days, Cheapflights users made a total of 200,618 searches

Fly to

Singapore

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 20-1

11:00-14:39

Nonstop2h 39m

Portland

Sat 24-1

16:10-18:18

Nonstop3h 08m

S$ 268

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 28-1

11:00-14:39

Nonstop2h 39m

Portland

Sat 31-1

16:10-18:18

Nonstop3h 08m

S$ 268

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 10-3

09:50-13:41

1 stop2h 51m

Grand Rapids Gerald R. Ford Intl

Wed 11-3

08:10-13:17

1 stop6h 07m

S$ 271

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 28-1

11:00-14:39

Nonstop2h 39m

Portland

Wed 4-2

11:10-18:31

1 stop8h 21m

S$ 281

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 20-1

11:00-14:39

Nonstop2h 39m

Portland

Wed 21-1

16:10-18:18

Nonstop3h 08m

S$ 283

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 16-5

08:55-16:15

1 stop6h 20m

Portland

Sat 23-5

16:50-20:24

1 stop4h 34m

S$ 294

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 20-1

07:00-13:45

1 stop5h 45m

Portland

Thu 22-1

12:43-21:05

2 stops9h 22m

S$ 300

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 20-1

14:50-00:20

2 stops8h 30m

Portland

Wed 21-1

06:00-13:40

2 stops8h 40m

S$ 307

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Sat 17-1

06:50-13:25

1 stop5h 35m

Grand Rapids Gerald R. Ford Intl

Sun 18-1

08:15-13:08

1 stop5h 53m

S$ 309

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 15-4

13:26-19:09

1 stop4h 43m

Grand Rapids Gerald R. Ford Intl

Sat 18-4

12:10-16:18

1 stop5h 08m

S$ 330

Flights are sorted by cheapest return flights first.

Deals found on 31-12

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 26 December 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 23 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$ 850). Flying from Chicago in December will prove the most costly (average of S$ 1,687). 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: JetBlue, United Airlines. As they depart for the following popular destinations: Singapore.

JetBlue
JetBlue
From S$ 2,827
United Airlines
United Airlines
From S$ 1,829

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (924 flights per day), Orlando (826 flights per day) and New York (768 flights per day).

San Francisco
San Francisco
From S$ 1,737
Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 54
Tokyo
Tokyo
From S$ 2,068
Boston Logan Intl
Boston Logan Intl
From S$ 220

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Las Vegas Harry Reid Intl, with prices starting at S$ 54. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 54
Pittsburgh
Pittsburgh
From S$ 60
Boston Logan Intl
Boston Logan Intl
From S$ 220
Raleigh-Durham
Raleigh-Durham
From S$ 358

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 United Airlines from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,124 reviews
Check prices

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,124 reviews
United Airlines
7.4
Good
9,124 reviews
Check prices

Entertainment

7.1

Crew

8.1

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

Browse thousands of different options on Cheapflights for your next trip

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Fly your favourite airline from Chicago

Browse through various options for flying your favourite airline from Chicago. Flight routes are based on user searches made on Cheapflights and were last updated on 31 December 2025.
United Airlines flights from Chicago to Singapore

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 31 December 2025.

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

    This month, the top selected destinations from Chicago are Ahmedabad, Mumbai, 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 December. 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$ 836 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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