S$ 128+ Cheap flights from Chicago

CHI — SIN
8 Dec — 15 Dec1
1 adult
1 adult, Economy, 0 bags

Find flights from Chicago within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoPhiladelphia

ORD Chicago O'Hare Intl - PHL Philadelphia

ORDPHL

Chicago O'Hare Intl

Sat 16-1

18:25-21:40

Nonstop2h 15m

Philadelphia

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 135

ChicagoDenver

ORD Chicago O'Hare Intl - DEN Denver Intl

ORDDEN

Chicago O'Hare Intl

Wed 2-12

06:21-13:38

1 stop8h 17m

Denver Intl

Wed 31-12

00:00-01:00

Nonstop0h 00m

S$ 135

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Wed 20-1

11:17-14:24

Nonstop2h 07m

Baltimore/Washington

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 136

ChicagoPhiladelphia

ORD Chicago O'Hare Intl - PHL Philadelphia

ORDPHL

Chicago O'Hare Intl

Sat 12-12

17:02-23:27

1 stop5h 25m

Philadelphia

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 147

ChicagoPhiladelphia

ORD Chicago O'Hare Intl - PHL Philadelphia

ORDPHL

Chicago O'Hare Intl

Tue 29-12

18:26-21:41

Nonstop2h 15m

Philadelphia

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 165

ChicagoPhiladelphia

ORD Chicago O'Hare Intl - PHL Philadelphia

ORDPHL

Chicago O'Hare Intl

Thu 26-11

07:07-10:17

Nonstop2h 10m

Philadelphia

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 165

ChicagoDenver

ORD Chicago O'Hare Intl - DEN Denver Intl

ORDDEN

Chicago O'Hare Intl

Wed 23-12

17:45-19:40

Nonstop2h 55m

Denver Intl

Wed 31-12

00:00-01:00

Nonstop0h 00m

S$ 170
Fastest return journey

ChicagoBaltimore

ORD Chicago O'Hare Intl - BWI Baltimore/Washington

ORDBWI

Chicago O'Hare Intl

Tue 1-12

10:55-14:01

Nonstop2h 06m

Baltimore/Washington

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 178

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Thu 10-12

14:39-18:00

Nonstop2h 21m

New York LaGuardia

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 191

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Sat 5-12

07:00-10:21

Nonstop2h 21m

New York LaGuardia

Wed 31-12

00:00-23:00

Nonstop0h 00m

S$ 191

Flights are sorted by cheapest return flights first.

Deals found on 8-11

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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$ 1,212). Flying from Chicago in December will prove the most costly (average of S$ 2,460). 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.

American Airlines
American Airlines
From S$ 645
JetBlue
JetBlue
From S$ 2,821
United Airlines
United Airlines
From S$ 2,053

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Orlando (843 flights per day), New York (793 flights per day) and Los Angeles (671 flights per day).

Philadelphia
Philadelphia
From S$ 645
Tokyo
Tokyo
From S$ 1,629
Las Vegas Harry Reid Intl
Las Vegas Harry Reid Intl
From S$ 53
Amman Queen Alia Intl
Amman Queen Alia Intl
From S$ 916

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
Orlando
Orlando
From S$ 190
Jacksonville
Jacksonville
From S$ 190
Boston Logan Intl
Boston Logan Intl
From S$ 228

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.

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 Atlanta, Ahmedabad, Boston. 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.

  • 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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