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Flights to Chicago

R9 772 Cheap flights to Chicago

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 21/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from South Africa to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Etihad Airways Logo
9:50 - 7:35
JNB
-
ORD
29h 45m1 stop
Etihad Airways Logo
13:10 - 8:20
ORD
-
JNB
35h 10m1 stop
R13 407Etihad Airways
Wed, Feb 11 - Wed, Feb 18
Ethiopian Air Logo
8:20 - 7:40
JNB
-
ORD
31h 20m2 stops
Ethiopian Air Logo
9:45 - 20:10
ORD
-
JNB
26h 25m1 stop
R13 741Ethiopian Air
Wed, Feb 11 - Wed, Feb 18
Turkish Airlines Logo
19:05 - 10:05
JNB
-
ORD
23h 00m1 stop
Turkish Airlines Logo
20:20 - 10:50
ORD
-
JNB
30h 30m1 stop
R14 324Turkish Airlines
Fri, Feb 13 - Fri, Feb 20
Turkish Airlines Logo
19:05 - 18:25
JNB
-
ORD
31h 20m1 stop
Turkish Airlines Logo
19:50 - 10:30
ORD
-
JNB
31h 40m1 stop
R14 374Turkish Airlines
Wed, Jan 28 - Wed, May 6
United Airlines Logo
20:50 - 18:37
CPT
-
ORD
29h 47m1 stop
United Airlines Logo
10:52 - 16:10
ORD
-
CPT
21h 18m2 stops
R15 592United Airlines
Fri, Jan 16 - Thu, Jan 29
United Airlines Logo
19:50 - 10:47
CPT
-
ORD
21h 57m1 stop
United Airlines Logo
14:25 - 15:20
ORD
-
CPT
17h 55m1 stop
R15 608United Airlines
Thu, May 21 - Sat, Jun 6
KLM Logo
21:30 - 9:53
CPT
-
MDW
20h 23m1 stop
KLM Logo
10:46 - 19:15
MDW
-
CPT
24h 29m1 stop
R17 009KLM
Mon, Jan 19 - Mon, Feb 2
KLM Logo
23:15 - 18:05
JNB
-
MDW
25h 50m2 stops
KLM Logo
13:00 - 21:20
MDW
-
JNB
25h 20m2 stops
R22 128KLM
Mon, May 25 - Sun, Jun 7
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m1 stop
R22 862Emirates
Thu, Feb 19 - Mon, Feb 23
Emirates Logo
18:40 - 15:45
DUR
-
ORD
28h 05m1 stop
Emirates Logo
20:35 - 16:35
ORD
-
DUR
37h 00m1 stop
R22 879Emirates
Thu, Apr 16 - Mon, May 11

momondo Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 13 550 searches and data was last updated on 30 December 2025.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 11/2

9:50-7:35

1 stop29h 45m

Chicago O'Hare Intl

Wed 18/2

13:10-8:20

1 stop35h 10m

R13 407

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 11/2

8:20-7:40

2 stops31h 20m

Chicago O'Hare Intl

Wed 18/2

9:45-20:10

1 stop26h 25m

R13 741

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 13/2

19:05-10:05

1 stop23h 00m

Chicago O'Hare Intl

Fri 20/2

20:20-10:50

1 stop30h 30m

R14 324

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 28/1

19:05-18:25

1 stop31h 20m

Chicago O'Hare Intl

Wed 6/5

19:50-10:30

1 stop31h 40m

R14 374

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 16/1

20:50-18:37

1 stop29h 47m

Chicago O'Hare Intl

Thu 29/1

10:52-16:10

2 stops21h 18m

R15 592

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 21/5

19:50-10:47

1 stop21h 57m

Chicago O'Hare Intl

Sat 6/6

14:25-15:20

1 stop17h 55m

R15 608

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Mon 19/1

21:30-9:53

1 stop20h 23m

Chicago Midway

Mon 2/2

10:46-19:15

1 stop24h 29m

R17 009

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Mon 25/5

23:15-18:05

2 stops25h 50m

Chicago Midway

Sun 7/6

13:00-21:20

2 stops25h 20m

R22 128

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Thu 19/2

19:10-14:55

1 stop27h 45m

Chicago O'Hare Intl

Mon 23/2

19:45-17:10

1 stop37h 25m

R22 862

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Thu 16/4

18:40-15:45

1 stop28h 05m

Chicago O'Hare Intl

Mon 11/5

20:35-16:35

1 stop37h 00m

R22 879

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

Chicago flights insights and trends

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

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 R15 975. 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 R16 626.

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 090 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 309 on momondo.

Cheapest flights to Chicago

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

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

R9 772

Best Round-Trip Price

R13 407

Fastest flight time

28h 41m

Popular in

November
The best one-way flight price to Chicago from South Africa in the last 72 hours is R9 772 (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 R13 407 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 28h 41m (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
November has the highest demand for flights to Chicago, with a 7% 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 R17 878.

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 611. 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 December 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.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond

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.

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to Chicago

Popular Flights to Chicago

Popular routes according to searches in the past day on momondo
Johannesburg to Chicago Flightsfrom R804
Cape Town Intl to Chicago Flightsfrom R902
Durban King Shaka Intl to Chicago Flightsfrom R1 018