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S$ 164+ Cheap flights from Chicago

CHI — SIN
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

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Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

ChicagoGrand Rapids

ORD Chicago O'Hare Intl - GRR Grand Rapids Gerald R. Ford Intl

ORDGRR

Chicago O'Hare Intl

Tue 13-10

21:50-23:54

Nonstop1h 04m

Grand Rapids Gerald R. Ford Intl

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 168

ChicagoGrand Rapids

ORD Chicago O'Hare Intl - GRR Grand Rapids Gerald R. Ford Intl

ORDGRR

Chicago O'Hare Intl

Tue 8-12

08:39-15:09

1 stop5h 30m

Grand Rapids Gerald R. Ford Intl

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 181

ChicagoGrand Rapids

ORD Chicago O'Hare Intl - GRR Grand Rapids Gerald R. Ford Intl

ORDGRR

Chicago O'Hare Intl

Thu 21-1

19:35-23:47

1 stop3h 12m

Grand Rapids Gerald R. Ford Intl

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 181

ChicagoGrand Rapids

ORD Chicago O'Hare Intl - GRR Grand Rapids Gerald R. Ford Intl

ORDGRR

Chicago O'Hare Intl

Tue 10-11

17:05-20:59

1 stop2h 54m

Grand Rapids Gerald R. Ford Intl

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 181

ChicagoOntario

ORD Chicago O'Hare Intl - ONT Ontario

ORDONT

Chicago O'Hare Intl

Fri 23-10

15:49-23:42

1 stop9h 53m

Ontario

Wed 31-12

00:00-02:00

Nonstop0h 00m

S$ 188

ChicagoOntario

ORD Chicago O'Hare Intl - ONT Ontario

ORDONT

Chicago O'Hare Intl

Sat 6-3

05:30-11:27

1 stop7h 57m

Ontario

Wed 31-12

00:00-02:00

Nonstop0h 00m

S$ 201

ChicagoOntario

ORD Chicago O'Hare Intl - ONT Ontario

ORDONT

Chicago O'Hare Intl

Wed 16-12

19:18-23:58

1 stop6h 40m

Ontario

Wed 31-12

00:00-02:00

Nonstop0h 00m

S$ 201

ChicagoOntario

ORD Chicago O'Hare Intl - ONT Ontario

ORDONT

Chicago O'Hare Intl

Fri 5-3

18:59-23:48

1 stop6h 49m

Ontario

Wed 31-12

00:00-02:00

Nonstop0h 00m

S$ 201

ChicagoOntario

ORD Chicago O'Hare Intl - ONT Ontario

ORDONT

Chicago O'Hare Intl

Mon 1-3

18:59-23:48

1 stop6h 49m

Ontario

Wed 31-12

00:00-02:00

Nonstop0h 00m

S$ 201

ChicagoOntario

ORD Chicago O'Hare Intl - ONT Ontario

ORDONT

Chicago O'Hare Intl

Sat 3-10

14:05-22:40

2 stops10h 35m

Ontario

Wed 31-12

00:00-02:00

Nonstop0h 00m

S$ 207

Flights are sorted by cheapest return flights first.

Deals found on 9-9

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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

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago?

Currently, January is the cheapest month in which you can book a flight from Chicago (average of S$ 1,189). Flying from Chicago in December will prove the most costly (average of S$ 2,405). 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$ 2,785
United Airlines
United Airlines
From S$ 2,027

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (963 flights per day), Detroit (826 flights per day) and Los Angeles (771 flights per day).

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 53
Amman Queen Alia Intl
Amman Queen Alia Intl
From S$ 904
Detroit
Detroit
From S$ 1,662
Jacksonville
Jacksonville
From S$ 188

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$ 53. Explore other affordable destinations below.

Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 53
Jacksonville
Jacksonville
From S$ 188
Boston Logan Intl
Boston Logan Intl
From S$ 225
New York
New York
From S$ 377

When is the best time to book a flight from Chicago?

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 41 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Airline reviews for flights from Chicago

Read reviews from past customers who have flown Etihad Airways from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Etihad Airways
7.3
Good
1,534 reviews
Check prices

Entertainment

7.2

Overall

7.3

Boarding

7.6

Comfort

7.3

Food

7.1

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Tom,May 2026

JFK - AUH

Everything was good except the lie flat bed. The bed has a gap and is uncomfortable to lie on. The hostesses were great; the food service was reasonable and the connecting flight services and the baggage service were good. Entertainment service was also good.
Etihad Airways
7.3
Good
1,534 reviews
Etihad Airways
7.3
Good
1,534 reviews
Check prices

Entertainment

7.2

Overall

7.3

Boarding

7.6

Comfort

7.3

Food

7.1

Crew

7.8

Reviews

1 / 20
8.0
Excellent

Tom,May 2026

JFK - AUH

Everything was good except the lie flat bed. The bed has a gap and is uncomfortable to lie on. The hostesses were great; the food service was reasonable and the connecting flight services and the baggage service were good. Entertainment service was also good.

Browse thousands of different options on Cheapflights for your next trip

Related info for your journey

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

    This month, the top selected destinations from Chicago are Boston, Atlanta, Athens. 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 January. 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$ 1,030 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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Fly with Cheapflights

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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