Which airlines fly to Chicago?

For flights from South Africa to Chicago, most momondo users will book with popular airlines such as British Airways, Turkish Airlines, United Airlines and KLM. Depending on what airport you fly from, you may have other airlines to choose from.

Emirates Flights to Chicago

Emirates is a popular choice for users travelling to Chicago. It operates 14 flights every week to Chicago, most often flying from Cancun. Emirates ticket prices will depend on when and where you need to fly from - deals as low as R18 860 (from Johannesburg OR Tambo) have been found by momondo users. In 3 414 reviews, momondo users have rated Emirates at an average score of 8,1/10.

Virgin Atlantic Flights to Chicago

Another popular choice for flights to Chicago is Virgin Atlantic (7,5/10, 673 reviews). Most Virgin Atlantic flights landing in Chicago will be arriving from Minneapolis St Paul, but there are 46 Virgin Atlantic flights to Chicago from all departure points globally so prices can vary significantly. The best Virgin Atlantic deal found on momondo this week was R15 714 (Johannesburg OR Tambo to Chicago, return).

How long does it take to fly to Chicago?

Flight times from South Africa to Chicago vary, but if you’re flying out of Johannesburg OR Tambo and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 21h 46m on average. Another popular route from South Africa to Chicago is flying from Cape Town Intl to Chicago O'Hare Intl, which will take roughly 22h 37m. Keep in mind that layovers or delays could extend your travel time.

R11 434 Cheap Flights to Chicago in 2025/26

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16:00 - 10:05DUR-ORD

26h 05m2 stops

20:20 - 13:30ORD-DUR

33h 10m2 stops

R14 899Turkish Airlines

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Sun, Feb 1 - Sat, Feb 28

7:00 - 18:25DUR-ORD

43h 25m2 stops

21:50 - 13:55ORD-DUR

32h 05m2 stops

R16 486Lufthansa

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Tue, Jan 20 - Tue, Feb 24

9:30 - 18:52CPT-ORD

41h 22m2 stops

12:38 - 18:00ORD-CPT

21h 22m2 stops

R18 449United Airlines

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Mon, Dec 1 - Sun, Jan 11

20:35 - 17:33CPT-ORD

27h 58m2 stops

21:45 - 12:40ORD-CPT

31h 55m2 stops

R18 705British Airways

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Wed, Mar 11 - Sun, Mar 15

8:20 - 7:40JNB-ORD

31h 20m2 stops

9:45 - 20:10ORD-JNB

26h 25m1 stop

R18 841Ethiopian Air

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Fri, Dec 26 - Tue, Dec 30

14:30 - 7:40JNB-ORD

25h 10m2 stops

9:45 - 20:10ORD-JNB

26h 25m1 stop

R18 978Ethiopian Air

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Fri, Dec 26 - Tue, Dec 30

18:55 - 19:45CPT-ORD

31h 50m1 stop

21:45 - 12:40ORD-CPT

31h 55m2 stops

R19 285British Airways

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Wed, Mar 11 - Sun, Mar 15

19:10 - 14:55DUR-ORD

27h 45m1 stop

19:45 - 17:10ORD-DUR

37h 25m1 stop

R21 060Emirates

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Sun, Feb 1 - Sat, Feb 28

20:50 - 13:09CPT-ORD

24h 19m2 stops

18:21 - 7:40ORD-CPT

53h 19m2 stops

R22 545United Airlines

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Tue, Dec 16 - Tue, Dec 23

19:10 - 14:55DUR-ORD

27h 45m1 stop

19:45 - 17:10ORD-DUR

37h 25m1 stop

R24 183Emirates

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Sat, Feb 14 - Wed, Feb 18

Fly from

Route

Depart

Return

Price

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sun 1/2

16:00-10:05

2 stops26h 05m

Chicago O'Hare Intl

Sat 28/2

20:20-13:30

2 stops33h 10m

R14 899

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Tue 20/1

7:00-18:25

2 stops43h 25m

Chicago O'Hare Intl

Tue 24/2

21:50-13:55

2 stops32h 05m

R16 486

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 1/12

9:30-18:52

2 stops41h 22m

Chicago O'Hare Intl

Sun 11/1

12:38-18:00

2 stops21h 22m

R18 449

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 11/3

20:35-17:33

2 stops27h 58m

Chicago O'Hare Intl

Sun 15/3

21:45-12:40

2 stops31h 55m

R18 705

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 26/12

8:20-7:40

2 stops31h 20m

Chicago O'Hare Intl

Tue 30/12

9:45-20:10

1 stop26h 25m

R18 841

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 26/12

14:30-7:40

2 stops25h 10m

Chicago O'Hare Intl

Tue 30/12

9:45-20:10

1 stop26h 25m

R18 978

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 11/3

18:55-19:45

1 stop31h 50m

Chicago O'Hare Intl

Sun 15/3

21:45-12:40

2 stops31h 55m

R19 285

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sun 1/2

19:10-14:55

1 stop27h 45m

Chicago O'Hare Intl

Sat 28/2

19:45-17:10

1 stop37h 25m

R21 060

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 16/12

20:50-13:09

2 stops24h 19m

Chicago O'Hare Intl

Tue 23/12

18:21-7:40

2 stops53h 19m

R22 545

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sat 14/2

19:10-14:55

1 stop27h 45m

Chicago O'Hare Intl

Wed 18/2

19:45-17:10

1 stop37h 25m

R24 183

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Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

Prices

Other information

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from South Africa, with most prices found around R16 350. If you are unable to visit Chicago during the month of February, then departing from South Africa during the month September is also very affordable. Most momondo users find prices during this month for around R17 032.

What is the cheapest day to depart on your flight to Chicago?

On average, the least expensive day to fly to Chicago from South Africa is on a Thursday. momondo users have found tickets for Thursday departures for as low as R17 829. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Saturday is R19 862.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest South Africa to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as R17 750. Try not to purchase tickets in the morning because they tend to be around R19 802. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from South Africa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R18 335 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from South Africa for as low as R16 725 on momondo.

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport

Find flights from Johannesburg OR Tambo Airport to Milwaukee

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price	R11 434
Best Round-Trip Price	R14 899
Fastest flight time	24h 50m
Popular in	March

The best one-way flight price to Chicago from South Africa in the last 72 hours is R11 434 (Johannesburg OR Tambo to Chicago O'Hare Intl).

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The best round-trip flight price to Chicago from South Africa in the last 72 hours is R14 899 (Durban King Shaka Intl to Chicago O'Hare Intl).

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The fastest flight to Chicago from South Africa takes 24h 50m (Cape Town Intl to Chicago O'Hare Intl).

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March has the highest demand for flights to Chicago, with a 6% price increase on average.

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Frequently asked questions about flying to Chicago

When is it best to fly to Chicago to go sightseeing?

Most momondo users would consider May and June to be the best times to fly to Chicago to see sights like Chicago Riverwalk. Typically, the weather in Chicago is under 70 degrees Fahrenheit (21°C) but still warm and the chance of rain is only moderate.

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from South Africa is 69 days out, which is when prices tend to be around R18 235.

Is there an alternative airport near Chicago?

Those flying to Chicago could potentially find better pricing at Chicago Midway Airport (14 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre) depending on the month and departure airport.

Is there a cheaper alternative to flying into Chicago?

Prices vary based on where travellers are departing from, but on average, the cheapest airport to fly to in Chicago is Chicago Midway Airport where the average price is R2 417. Users typically find the best prices when using momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Edgewater?

Yes, if you fly to Chicago O'Hare Intl in Chicago which is the closest available airport to Edgewater (20,1 km away).

What’s the closest airport to McCormick Place?

The closest airport to McCormick Place is 12,7 km away - Chicago’s Chicago Midway airport.

When did momondo last update prices for flights to Chicago?

Prices for flights to Chicago were last updated today.

How many operators does momondo search for flights to Chicago?

As of November 2025, there are 12 operators available to choose from for flights to Chicago.

How old do you have to be to fly to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's licence and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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Why use momondo?

Why should I use momondo to find a flight deal to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago.

Can I find flights to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for flights to Chicago to just show those with flexible booking policies.

How can momondo help me find flights to Chicago?

Once all potential Chicago flight options are in front of you momondo lets you sort and filter flights based on preferences such as airline, price and flight times, amongst many other options.