S$ 64+ 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 24-12. 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
14 Dec — 21 Dec1
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 14 November 2025.

Good round-trip deal

S$ 363 or less

Good one-way deal

S$ 56 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

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 14 November 2025.

Tue 17-210:35ORD - GRR
Nonstop1h 10mUnited Airlines
Wed 18-309:00GRR - ORD
Nonstop1h 12mUnited Airlines
Deal found 12-11S$ 139
Wed 10-1218:00ORD - GRR
1 stop4h 54mDelta
Wed 17-1215:37GRR - ORD
1 stop5h 58mDelta
Deal found 12-11S$ 204
Tue 17-218:20ORD - GRR
Nonstop0h 58mUnited Airlines
Tue 17-306:00GRR - ORD
Nonstop1h 13mUnited Airlines
Deal found 12-11S$ 217
Thu 25-1218:02ORD - GRR
1 stop3h 19mDelta
Sat 10-108:10GRR - ORD
1 stop5h 57mDelta
Deal found 12-11S$ 226
Wed 10-1209:05ORD - GRR
Nonstop1h 07mUnited Airlines
Wed 17-1212:56GRR - ORD
Nonstop1h 19mUnited Airlines
Deal found 12-11S$ 230
Sat 6-1206:45ORD - GRR
1 stop5h 37mDelta
Sat 6-1218:00GRR - ORD
1 stop3h 35mDelta
Deal found 12-11S$ 248
Tue 24-308:45ORD - GRR
Nonstop1h 09mUnited Airlines
Wed 25-309:00GRR - ORD
Nonstop1h 12mUnited Airlines
Deal found 11-11S$ 269
Mon 16-206:30ORD - GRR
1 stop6h 04mDelta
Tue 17-316:00GRR - ORD
1 stop3h 46mDelta
Deal found 12-11S$ 273
Fri 26-1221:18ORD - GRR
Nonstop1h 12mUnited Airlines
Sat 10-109:00GRR - ORD
Nonstop1h 19mUnited Airlines
Deal found 13-11S$ 280
Tue 24-317:45ORD - GRR
1 stop5h 02mDelta
Wed 25-305:20GRR - ORD
1 stop5h 15mDelta
Deal found 12-11S$ 297
Tue 17-218:20ORD - GRR
Nonstop0h 58mUnited Airlines
Thu 19-307:15GRR - ORD
Nonstop1h 12mUnited Airlines
Deal found 12-11S$ 299
Tue 17-215:59ORD - GRR
1 stop5h 50mDelta
Fri 20-316:00GRR - ORD
1 stop3h 46mDelta
Deal found 12-11S$ 307

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 November 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 17-2

10:35-12:45

Nonstop1h 10m

Grand Rapids Gerald R. Ford Intl

Wed 18-3

09:00-09:12

Nonstop1h 12m

S$ 139

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 18-2

14:03-21:06

1 stop6h 03m

Grand Rapids Gerald R. Ford Intl

Tue 17-3

16:00-18:46

1 stop3h 46m

S$ 204

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 17-2

18:20-20:18

Nonstop0h 58m

Grand Rapids Gerald R. Ford Intl

Tue 17-3

06:00-06:13

Nonstop1h 13m

S$ 217

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 18-2

21:46-23:53

Nonstop1h 07m

Grand Rapids Gerald R. Ford Intl

Wed 18-3

06:00-06:13

Nonstop1h 13m

S$ 217

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Thu 1-1

18:02-22:21

1 stop3h 19m

Grand Rapids Gerald R. Ford Intl

Mon 5-1

10:27-13:07

1 stop3h 40m

S$ 226

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Wed 10-12

09:05-11:12

Nonstop1h 07m

Grand Rapids Gerald R. Ford Intl

Wed 17-12

12:56-13:15

Nonstop1h 19m

S$ 230

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 24-3

08:45-10:54

Nonstop1h 09m

Grand Rapids Gerald R. Ford Intl

Wed 25-3

09:00-09:12

Nonstop1h 12m

S$ 269

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Mon 16-2

06:30-13:34

1 stop6h 04m

Grand Rapids Gerald R. Ford Intl

Tue 17-3

16:00-18:46

1 stop3h 46m

S$ 273

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Tue 24-3

10:35-15:17

1 stop3h 42m

Grand Rapids Gerald R. Ford Intl

Wed 25-3

05:20-09:35

1 stop5h 15m

S$ 273

ChicagoGrand Rapids

ORD - GRR

ORDGRR

Chicago O'Hare Intl

Fri 26-12

21:18-23:30

Nonstop1h 12m

Grand Rapids Gerald R. Ford Intl

Sat 10-1

09:00-09:19

Nonstop1h 19m

S$ 280

Flights are sorted by cheapest return flights first.

Deals found on 13-11

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 7 November 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$ 860). Flying from Chicago in June will prove the most costly (average of S$ 1,560). 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$ 927

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,565 flights per day), Detroit (1,104 flights per day) and Los Angeles (686 flights per day).

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 54
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 531
Raleigh-Durham
Raleigh-Durham
From S$ 363
Krakow J. Paul II Balice
Krakow J. Paul II Balice
From S$ 1,190

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
Raleigh-Durham
Raleigh-Durham
From S$ 363
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From S$ 531

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 Boston
Direct flights from Seattle
Direct flights from Las Vegas
Direct flights from Orlando
Direct flights from Miami
Direct flights from Atlanta
Direct flights from Austin
Direct flights from Denver
Direct flights from Portland
Direct flights from Anchorage
Direct flights from San Diego
Direct flights from Minneapolis
Direct flights from Philadelphia
Direct flights from Charlotte
Direct flights from Tampa
Direct flights from Nashville
Direct flights from Buffalo
Direct flights from New Orleans
Direct flights from Indianapolis
Direct flights from Salt Lake City
Direct flights from Pittsburgh
Direct flights from Cincinnati
Direct flights from St. Louis
Direct flights from Cleveland
Direct flights from San Antonio
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 14 November 2025.

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

    This month, the top selected destinations from Chicago are Mumbai, Atlanta, Ahmedabad. 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 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$ 842 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.