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 priceR15 551Average for round-trip flights in July 2021
Round-trip fromR11 182From Johannesburg OR Tambo to Chicago
One-way fromR148One-way flight from Johannesburg to Chicago

Cheap flights to Chicago in July, August 2021

The best prices found for ORD flights for July, August
11 Aug - 13 Sep
R14 099pp
JNB
Johannesburg OR Tambo
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
KLM
   
2 STOPS
JNB
Johannesburg OR Tambo
11 Aug - 13 Sep
R14 232pp
JNB
Johannesburg OR Tambo
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
KLM
 
1 STOP
JNB
Johannesburg OR Tambo
27 Jul - 3 Aug
R14 469pp
JNB
Johannesburg OR Tambo
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
JNB
Johannesburg OR Tambo

Chicago 2021 flight deals

Cheap flights to Chicago found for this year
1 Oct - 4 Oct
R11 093pp
JNB
Johannesburg OR Tambo
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
JNB
Johannesburg OR Tambo
10 Sep - 10 Oct
R11 182pp
JNB
Johannesburg OR Tambo
British Airways
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
British Airways
 
1 STOP
JNB
Johannesburg OR Tambo
10 Sep - 10 Oct
R11 211pp
JNB
Johannesburg OR Tambo
British Airways
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
British Airways
 
1 STOP
JNB
Johannesburg OR Tambo

Last minute flights to Chicago

Late deals on return flights to Chicago, departing today and this week
6 Aug - 14 Aug
R14 692pp
JNB
Johannesburg OR Tambo
KLM
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
KLM
 
1 STOP
JNB
Johannesburg OR Tambo
6 Aug - 14 Aug
R14 766pp
JNB
Johannesburg OR Tambo
KLM
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
KLM
   
2 STOPS
JNB
Johannesburg OR Tambo
6 Aug - 13 Aug
R19 905pp
JNB
Johannesburg OR Tambo
Multiple airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Qatar Airways
 
1 STOP
JNB
Johannesburg OR Tambo

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 992
February
R11 546
March
R13 616
April
R14 086
May
R13 468
June
R15 150
July
R14 764
August
R14 921
September
R13 738
October
R13 456
November
R13 210
December
R15 533
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 546 - R21 055
CHI
Temperature
1 - 29 °C
CHI
Precipitation
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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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 July 27, 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 July 27, 2021.
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