Cheap Flights to Chicago

Return
Economy
Washington (WAS)
Chicago (CHI)
Sun 24-10
Sun 31-10
Any month
|
Home North America USA Illinois Cheap flights to Chicago, Illinois

Flights to Chicago in 2021

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
Popular inJanuaryHigh demand for flights, 5% potential price rise
Cheapest inSeptemberBest time to find cheap flights, 1% potential price drop
Average priceS$ 1,374Average for round-trip flights in October 2021
Round-trip fromS$ 1,078From Singapore Changi to Chicago
One-way fromS$ 13One-way flight from Singapore Changi (SIN) to Chicago

Cheap flights to Chicago in October, November 2021

The best prices found for ORD flights for October, November
8 Nov - 18 Nov
S$ 1,087pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi
18 Nov - 18 Feb
S$ 1,089pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi
15 Nov - 20 Nov
S$ 1,093pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
8 Nov - 18 Nov
S$ 1,087pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi
18 Nov - 18 Feb
S$ 1,089pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi
15 Nov - 20 Nov
S$ 1,093pp
SIN
Singapore Changi
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
SIN
Singapore Changi

Last minute flights to Chicago

Late deals on return flights to Chicago, departing today and this week
22 Oct - 13 Nov
S$ 1,125pp
SIN
Singapore Changi
Japan Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Japan Airlines
   
2 STOPS
SIN
Singapore Changi
22 Oct - 13 Nov
S$ 1,147pp
SIN
Singapore Changi
Japan Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Japan Airlines
   
2 STOPS
SIN
Singapore Changi
22 Oct - 13 Nov
S$ 1,158pp
SIN
Singapore Changi
Japan Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Japan Airlines
   
2 STOPS
SIN
Singapore Changi

COVID Restrictions

View COVID Travel Restrictions for Chicago

Can I fly to Chicago from USA right now?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from USA need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from USA must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from USA are not required to quarantine after entering Chicago.

Can I fly back to USA from Chicago?

Returning to USA from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to USA.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering USA.

Hide COVID Travel Restrictions for Chicago

Cheapest prices for Chicago flights by month

The cheapest ticket to Chicago found for each month in 2021 based on historical flight searches by Cheapflights users.
May
S$ 1,403
July
S$ 1,232
August
S$ 1,271
October
S$ 1,238
Currently, is the cheapest month in which you can book a flight to Chicago. Flying to Chicago in May will prove the most costly. There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the best time to fly to Chicago?

Average Chicago flight ticket prices and weather conditions for 2021 and 2022 by month.
SIN - CHI
Price
S$ 1,058 - S$ 1,898
CHI
Temperature
1 - 29 °C
CHI
Precipitation
17 - 109 mm
The best time to fly to Chicago is during September, but great deals can be found at other times. July sees the temperatures in Chicago peak to their warmest. May tends, on average, to see the most amount of rainfall.

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

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 61 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Which day is cheapest to fly to Chicago?

Friday is currently, on average, the cheapest day to fly to Chicago. Flying on Saturday will result in higher flight prices.

What time of day is cheapest to fly to Chicago?

Flights in the afternoon are typically the cheapest time of the day to fly to Chicago. Flights at midday are usually the most expensive.

As Frank Sinatra crooned, “Chicago is my kind of town.” And many visitors agree. A trip to Chicago is best spent shopping on the Miracle Mile, stepping back in time at the National History Museum, touring the artist’s lofts in the heart of the city, and enjoying some cool jazz at one of Chicago’s many jazz clubs.

Chicago, with its varied and eclectic sampling of modern architecture, rests on the shores of Lake Michigan in the heart of the American Midwest. Flights to Chicago land travellers at either Midway Airport or O’Hare International Airport, both about 30 minutes from downtown Chicago, but a car isn’t needed to get around. Take a taxi or hop the commuter rail from your Chicago flight to downtown and then tour the city by foot. Stop by the Sears Tower, the tallest building in the United States, and take an elevator ride to the Sears Tower Skydeck for unprecedented views of the city.

Search and compare: cheap flights to Chicago

Back to top

Chicago climate

Chicago has an extreme climate with very hot summers and bitterly cold winters, its lakeside setting only slightly moderating the temperatures and adding some humidity to the atmosphere. Chicago has distinct seasons, with a short spring, when temperatures are moderate and nights frosty. Summers are hot, sunny and humid, from June to the end of September, with cool evenings when breezes blow in from Lake Michigan. Autumn is a lovely time of year when the air is crisp and cool, with blue skies and sunshine. Winters in Chicago are icy and prone to cold, harsh winds. Snow is common, and it is also very rainy during the winter months.

Back to top

When is the best time to fly to Chicago?

Peak season:

Summer is the peak of the festival season in the Chicago area with major events taking place in the parks and neighbourhoods every weekend, in spite of the heat and humidity from the Lake.  September can be the most enjoyable and mild month of the year but there’s less going on during this period.

Off season:

January to March is when Chicago is least busy and deals on hotels and cheap flights to Chicago are usually attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.

Search and compare: cheap flights to Chicago

Back to top

Getting around Chicago

No need to worry about getting around Chicago. There are plenty of ways to get around. Hop on the El, short for elevated train, the city’s subway system, or one of the buses that runs all over the city. For information about fares and routes, check out the website for the Chicago Transit Authority. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Biking is becoming increasingly popular around the city, thanks to the city’s former mayor encouraging residents to ride their bikes as a mode of transportation. With all of Chicago’s lakefront property, biking can be a great way to enjoy the city. 

Back to top

Alternative, similarly priced destinations

See alternative destinations where airfare is generally forecast to be close to Chicago flight prices.

Find the best prices for you!

Cheap tickets to Chicago found by our users in Singapore as recently as October 17, 2021.

Chicago, Illinois airports

See all airports in Chicago, select one to find and compare flight prices.

Cheapest flights to USA

Not set on Chicago? See the cheapest flights to Singapore. Airfare prices updated on October 17, 2021.
Home North America USA Illinois Cheap flights to Chicago, Illinois
  • Return
  • One-way
  • Multi-city
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First