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S$ 76+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 17-2. 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
11 Jan — 18 Jan1
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 12 December 2025.

Good round-trip deal

S$ 361 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 12 December 2025.

Tue 10-210:35ORD - GRR
1 stop3h 42mDelta
Wed 11-216:00GRR - ORD
1 stop6h 05mDelta
Deal found 10-12S$ 203
Tue 20-118:00ORD - GRR
1 stop4h 57mDelta
Sat 24-116:00GRR - ORD
1 stop6h 05mDelta
Deal found 11-12S$ 225
Mon 26-110:35ORD - GRR
1 stop3h 42mDelta
Thu 26-210:24GRR - ORD
1 stop3h 58mDelta
Deal found 11-12S$ 247
Wed 24-1221:18ORD - GRR
Nonstop1h 10mUnited Airlines
Wed 31-1209:30GRR - ORD
Nonstop1h 24mUnited Airlines
Deal found 10-12S$ 260
Tue 17-221:46ORD - GRR
Nonstop1h 07mUnited Airlines
Sat 21-217:01GRR - ORD
Nonstop1h 09mUnited Airlines
Deal found 9-12S$ 264
Sat 10-111:00ORD - PWM
Nonstop2h 39mUnited Airlines
Sat 17-116:10PWM - ORD
Nonstop3h 08mUnited Airlines
Deal found 11-12S$ 270
Mon 5-118:25ORD - PWM
1 stop4h 55mDelta
Fri 9-105:30PWM - ORD
1 stop9h 10mDelta
Deal found 10-12S$ 296
Tue 6-111:05ORD - PWM
2 stops10h 22mDelta
Thu 8-106:00PWM - ORD
1 stop5h 55mDelta
Deal found 10-12S$ 302
Sat 10-106:15ORD - GRR
1 stop5h 53mDelta
Fri 16-112:12GRR - ORD
1 stop6h 43mDelta
Deal found 10-12S$ 305
Tue 6-113:55ORD - PWM
2 stops8h 27mDelta
Tue 13-112:48PWM - ORD
2 stops9h 17mDelta
Deal found 10-12S$ 309
Thu 1-118:21ORD - PWM
1 stop4h 38mUnited Airlines
Wed 7-116:10PWM - ORD
Nonstop3h 08mUnited Airlines
Deal found 10-12S$ 314
Thu 8-106:50ORD - GRR
1 stop5h 42mDelta
Mon 12-117:51GRR - ORD
1 stop4h 14mDelta
Deal found 11-12S$ 317

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 12 December 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 20-1

18:00-23:57

1 stop4h 57m

Grand Rapids Gerald R. Ford Intl

Sat 24-1

16:00-21:05

1 stop6h 05m

S$ 225

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 26-1

10:35-15:17

1 stop3h 42m

Grand Rapids Gerald R. Ford Intl

Thu 26-2

10:24-13:22

1 stop3h 58m

S$ 247

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 24-12

21:18-23:28

Nonstop1h 10m

Grand Rapids Gerald R. Ford Intl

Wed 31-12

09:30-09:54

Nonstop1h 24m

S$ 260

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 17-2

21:46-23:53

Nonstop1h 07m

Grand Rapids Gerald R. Ford Intl

Sat 21-2

17:01-17:10

Nonstop1h 09m

S$ 264

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 23-1

11:00-14:39

Nonstop2h 39m

Portland

Mon 26-1

16:10-18:18

Nonstop3h 08m

S$ 270

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6-1

14:50-22:27

1 stop6h 37m

Portland

Thu 8-1

06:00-13:26

1 stop8h 26m

S$ 296

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 11-1

06:50-12:08

1 stop4h 18m

Portland

Wed 14-1

12:48-18:28

1 stop6h 40m

S$ 296

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10-1

08:52-14:29

1 stop4h 37m

Portland

Sat 17-1

08:40-13:15

1 stop5h 35m

S$ 296

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 5-1

18:25-00:20

1 stop4h 55m

Portland

Fri 9-1

05:30-13:40

1 stop9h 10m

S$ 296

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6-1

17:20-23:22

1 stop5h 02m

Portland

Tue 13-1

14:35-21:35

1 stop8h 00m

S$ 296

Flights are sorted by cheapest return flights first.

Deals found on 12-12

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 5 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$ 854). Flying from Chicago in December will prove the most costly (average of S$ 1,757). 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$ 2,846
United Airlines
United Airlines
From S$ 1,916

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,490 flights per day), Detroit (948 flights per day) and Minneapolis (655 flights per day).

Doha Hamad Intl
Doha Hamad Intl
From S$ 2,846
San Francisco
San Francisco
From S$ 1,748
Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 54
Tokyo
Tokyo
From S$ 2,081

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
New York
New York
From S$ 89
Boston Logan Intl
Boston Logan Intl
From S$ 222

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
9,095 reviews
Check prices

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,095 reviews
United Airlines
7.4
Good
9,095 reviews
Check prices

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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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 12 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 12 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, 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 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.

  • 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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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.

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