Cheap Flights to Chicago

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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, 4% potential price rise
Cheapest inMarchBest time to find cheap flights, 2% potential price drop
Average priceR14 043Average for round-trip flights in April 2021
Round-trip fromR10 518From Johannesburg to Chicago
One-way fromR143One-way flight from Johannesburg to 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.
January
R12 519
February
R11 126
March
R13 121
April
R13 573
May
R12 978
June
R14 598
July
R14 227
August
R14 378
September
R13 238
October
R12 966
November
R12 729
December
R14 968
February is currently the cheapest month to fly to Chicago. At this moment in time December is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

When is the best time to fly to Chicago?

Average Chicago flight ticket prices and weather conditions for 2021 and 2022 by month.
JNB - CHI
Price
R11 126 - R20 289
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Peak season:

If you’ve been to New York then why not book cheap flights to Chicago, the nation’s second city? The skyscraper metropolis is a feat of modern architecture, as well as home to what was once the world’s tallest building, Sears Tower. It is not a traditional tourist destination but as the hub of the Midwest, Chicago much to offer as a holiday destination. Featuring world-class art galleries and science museums, huge parks and sandy beaches, it also has a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups). Peak tourist season is summer (June to August). This coincides with the festival season with many major events taking place in Chicago parks and neighbourhoods every weekend, in spite of the heat and humidity. Taste of Chicago, an outdoor food festival which showcases the variety of cuisines and local flavours, is in mid-July at the lakefront. If you book flights to Chicago during this popular festival, expect crowds of visitors in the area and a rise in the price of flight tickets. August is host to another popular event – the Chicago Air and Water Show. With its free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.

Off season:

Chicago is least busy in January through March making cheap flights to Chicago and hotel deals 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.

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

Savvy travellers are always on the lookout for the cheapest flights to Chicago but one of the biggest challenges for figuring out when to go can be the weather. If you don’t enjoy extreme temperatures, fiercely hot summers and bitterly cold winters, then give these two seasons a miss. April through May or September through October are the most enjoyable and mild months of the year in Chicago. You’ll still get warm weather and the hotel rates are more reasonable.

Which day is cheapest to fly to Chicago?

The cheapest flights to Chicago are usually found when departing on a Tuesday. The departure day with the highest cost at present is Friday.

What time of day is cheapest to fly to Chicago?

Chicago flights can be made cheaper if you choose a flight at midday. Booking a flight in the afternoon will likely mean higher prices.

How long is the flight to Chicago?

Flights from London to Chicago: 8 hours 50 minutes.

Flights from Manchester to Chicago: 8 hours 40 minutes.

Flights from Birmingham to Chicago: 10 hours 30 minutes.

Flights from Glasgow to Chicago: 10 hours 10 minutes.

Which airlines operate flights to Chicago?

There are plenty of direct daily flights to Chicago departing from London Heathrow with airlines such as British Airways, United Airlines and Virgin Atlantic. Connecting flights with various European airlines are available but will add a couple of hours to the flight time. The quickest direct flight to Chicago from Manchester is with American Airlines. Flights from other UK cities will require a connecting flight.

How to get from the airport to the city centre?

Flights to Chicago land at O’Hare International Airport (ORD) located in the city’s northwest corner, about 17 miles away from the CBD or Chicago Loop. Trains and buses provide efficient transportation to city centre and suburbs. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available from the airport.

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Cheap flights to Chicago in April, May 2021

The best prices found for ORD flights for April, May
23 Apr - 30 Apr
R10 318pp
JNB
Johannesburg OR Tambo
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
JNB
Johannesburg OR Tambo
21 Apr - 1 May
R10 332pp
JNB
Johannesburg OR Tambo
Ethiopian Air
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Ethiopian Air
 
1 STOP
JNB
Johannesburg OR Tambo
27 Apr - 17 May
R10 489pp
JNB
Johannesburg OR Tambo
Ethiopian Air
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Ethiopian Air
 
1 STOP
JNB
Johannesburg OR Tambo

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
22 Oct - 26 Dec
R10 289pp
JNB
Johannesburg OR Tambo
Ethiopian Air
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Ethiopian Air
 
1 STOP
JNB
Johannesburg OR Tambo
23 Apr - 30 Apr
R10 318pp
JNB
Johannesburg OR Tambo
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
JNB
Johannesburg OR Tambo
21 Apr - 1 May
R10 332pp
JNB
Johannesburg OR Tambo
Ethiopian Air
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Ethiopian Air
 
1 STOP
JNB
Johannesburg OR Tambo

Last minute flights to Chicago

Late deals on return flights to Chicago, departing today and this week
27 Apr - 17 May
R10 489pp
JNB
Johannesburg OR Tambo
Ethiopian Air
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Ethiopian Air
 
1 STOP
JNB
Johannesburg OR Tambo
28 Apr - 1 Dec
R11 374pp
JNB
Johannesburg OR Tambo
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
JNB
Johannesburg OR Tambo
28 Apr - 1 Dec
R11 517pp
JNB
Johannesburg OR Tambo
Turkish Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Turkish Airlines
 
1 STOP
JNB
Johannesburg OR Tambo

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 South Africa as recently as April 22, 2021.
Other local departures to Chicago, Illinois from South Africa

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 South Africa. Airfare prices updated on April 22, 2021.
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