Book cheap flights to Chicago

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Discover the cheapest flights to Chicago
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The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Popular flight routes to Chicago

Johannesburg
Flights from Johannesburgto Chicago
11123R
10322R
Prime price per passenger
Cape Town
Flights from Cape Townto Chicago
15040R
14448R
Prime price per passenger
Durban
Flights from Durbanto Chicago
16097R
15505R
Prime price per passenger

How long is the flight to Chicago?

If you’re planning a trip to Chicago, we at eDreams have checked the most popular routes to help you plan ahead. From Johannesburg, the flight takes about 23h 31m; from Cape Town, around 23h 32m; and from Durban, roughly 24h 56m.
Flight Time (in hours)
JohannesburgCape TownDurban
0h 5h 10h 15h 20h 25h
23h 31m
23h 32m
24h 56m

How much does a flight to Chicago cost?

At eDreams you can find flights from Cape Town to Chicago starting from R 7 227, with an average price of R 13 493. If you depart from other cities such as Johannesburg, you can find tickets from R 9 198, and from Durban starting from R 15 024, according to data from the last 72 hours.
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Cape TownJohannesburgDurban
R 13 493
R 18 552
R 15 024
Cape TownCheapest
Cheapest Price: R 7 227
Cheapest
Average

Find and book the best flights to Chicago

Chicago stands as a major hub in the United States, celebrated for its towering architecture and significant position on the shores of Lake Michigan. This metropolis serves as a gateway for journeys exploring the American Midwest, drawing visitors to its urban landscape.

Explore the city's rich history through its distinctive neighbourhoods and structures. The Willis Tower dominates the skyline, while the Art Institute of Chicago offers extensive collections. Millennium Park features prominent public art installations, and the historic Magnificent Mile provides a key urban experience.

Discover Chicago's character through its dynamic arts scene, architectural heritage, and diverse culinary offerings. Your destination presents a unique blend of cultural experiences and urban exploration, defining its appeal for many travellers.

When is the best time to fly to Chicago?

High Season (Summer)

Chicago's high season, typically from June to August, brings warm, sunny weather with average temperatures around 25°C. The city transforms into an outdoor hub, drawing both locals and visitors to its parks, lakefront, and numerous street festivals. Upon arrival, you'll encounter a lively atmosphere with people enjoying dining al fresco, boat tours on Lake Michigan, and strolls along the Riverwalk.

This period is defined by a lively energy and a calendar packed with cultural events. Grant Park hosts major music festivals like Lollapalooza and the Chicago Blues Festival, while neighbourhood fests celebrate local food and art. The days are long, encouraging outdoor activities and a bustling social scene that extends late into the evenings.

Low Season (Winter)

The low season in Chicago, primarily from December to March, is characterised by cold temperatures, averaging around -3°C, and frequent snowfall. The city takes on a quieter, more subdued pace, creating a distinct winter charm. When you land, you'll feel the crisp, often biting air, and see the urban landscape blanketed in snow.

Indoor activities become central to daily life during these months. Museums, theatres, and restaurants offer warmth and entertainment, and the holiday season brings festive lights and ice-skating rinks like those in Millennium Park. The city feels intimate and resilient, with locals embracing the winter weather as part of Chicago's unique identity.

Chicago bucket list: Best activities & sights

Touch down in Chicago and feel the city's pulse immediately. From the moment you arrive, Chicago's impressive skyline and welcoming energy beckon you to explore its unique blend of culture, history, and innovation. Discover a city that consistently reveals new layers of its character.

Millennium Park
This impressive urban park in downtown Chicago is home to captivating public art, including the reflective Cloud Gate sculpture, known affectionately as "The Bean". Its lively atmosphere perfectly blends nature with contemporary design.

Art Institute of Chicago
Step into one of the oldest and largest art museums in the United States. Its vast collection spans centuries and cultures, offering an immersive journey through global artistic achievements.

Navy Pier
Stretching into Lake Michigan, Navy Pier offers stunning city and lake views. It’s a lively spot to experience the city's connection to the water, perfect for a leisurely stroll or enjoying the atmosphere.

The Magnificent Mile
This stretch of Michigan Avenue is renowned for its grand architecture and bustling energy. It showcases Chicago's sophisticated style, from historic buildings to lively street life.

Museum of Science and Industry
Explore interactive exhibits housed in the historic Palace of Fine Arts building from the 1893 World's Columbian Exposition. This museum brings scientific principles to life with fascinating displays.

Chicago Riverwalk
Wander along the Chicago River on this scenic promenade, where you can admire the city's iconic architecture from a unique perspective. It provides a peaceful escape with continuous views of the urban landscape.

Field Museum
Discover natural history through vast collections covering everything from ancient civilisations to meteorites. The museum offers incredible insights into our planet's past and present.

Secure your seat to Chicago today

To find the best flight deals to Chicago, consider booking in advance and staying flexible with your travel dates. With eDreams, you can effortlessly compare flights, and if you're an eDreams Prime member, you'll unlock even more exclusive savings on your journey. Soon, you'll be on your way to discovering everything this exciting city has to offer.

Frequently asked questions about flights to Chicago

How can I find cheap flights to Chicago on eDreams?
At eDreams you will find flights from R1396 to Chicago. Thanks to the combination of various technologies, machine learning algorithms and real user searches on our platform, you will be able to choose between the different options that best suit your needs when you have to fly to Chicago.
When's the best time to book flights to Chicago?
By this we mean when travellers book their tickets. For the best time to actually travel to Chicago, read on.
When's the best time to go to Chicago?
According to our customers' flight searches, the best time to fly to Chicago is March.
The next best month to travel to Chicago is April.
And let's not forget February, the third top choice for travelling to Chicago.
However if you prefer things on the less busy side, we can highlight November as the least popular month for flights to Chicago.
What are the cheapest airlines flying to Chicago?

Looking at the prices of our customers' bookings from US to Chicago, your best bet for cheap flights is:

  • Air Canada: the average price of a one way flight is R15 226,29 . The average price of a Johannesburg ticket to Chicago is R15 226,29 and R19 251,10 if you leave from Cape Town.
  • Turkish Airlines: the average price of a one-way ticket is R18 532,14. The flight between Johannesburg and Chicago costs on average R16 618,06 and the ticket price from Cape Town round the R19 343,93.
Which airlines fly to Chicago?

Airlines flying direct from South Africa to Chicago include:

  • Spirit Airlines, with flights from Columbia, Newark, NJ and from Columbus, for example.
  • American Airlines also operates numerous flights, some of them originating from Atlanta, Dallas and Los Angeles.
  • Air Canada, with flights from Newark, NJ to Chicago and Seattle and also from Dallas.

Airlines with indirect flights to Chicago include:

  • Turkish Airlines, which flies from Johannesburg, Addis Ababa or Dubai.
  • Ethiopian Airlines, with flights from Cape Town and Johannesburg, as well as from Sishen.
  • Icelandair, with flights from Cape Town, George and also Durban.
How long before a flight to Chicago should I be at the airport?
If you want to be on time for your flight to Chicago, you should get to the airport at least two to three hours in advance. Check-ins, security controls, customs, and boarding the airplane can take some time. At eDreams, you can find the best deals for flights to Chicago departing from over 3 cities and choose from a variety of services that will improve your time at the airport and guarantee a much better travel experience, such as priority boarding and additional luggage. For more convenience, when booking your flight to Chicago with eDreams you can also add insurance or opt for a refundable fare and have a problem-free trip!

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