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Flights to Chicago

R9 826 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 12/4. 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.
Turkish Airlines Logo
19:05 - 19:25
JNB
-
ORD
31h 20m1 stop
Turkish Airlines Logo
20:10 - 10:30
ORD
-
JNB
31h 20m1 stop
R13 939Turkish Airlines
Fri, Mar 13 - Wed, Apr 15
Ethiopian Air Logo
13:50 - 8:15
CPT
-
ORD
25h 25m2 stops
Ethiopian Air Logo
10:15 - 14:35
ORD
-
CPT
21h 20m1 stop
R14 764Ethiopian Air
Thu, Apr 2 - Fri, Apr 10
Turkish Airlines Logo
19:05 - 18:25
JNB
-
ORD
31h 20m1 stop
Turkish Airlines Logo
20:20 - 10:50
ORD
-
JNB
30h 30m1 stop
R14 830Turkish Airlines
Sun, Feb 22 - Sun, Mar 1
United Airlines Logo
20:50 - 18:37
CPT
-
ORD
29h 47m1 stop
United Airlines Logo
18:17 - 16:10
ORD
-
CPT
37h 53m1 stop
R15 755United Airlines
Fri, Jan 30 - Fri, Feb 6
United Airlines Logo
22:00 - 13:15
JNB
-
ORD
23h 15m2 stops
United Airlines Logo
9:25 - 18:30
ORD
-
JNB
26h 05m2 stops
R16 284United Airlines
Sun, Feb 8 - Wed, Sep 23
British Airways Logo
22:00 - 17:42
JNB
-
ORD
27h 42m2 stops
British Airways Logo
17:50 - 9:25
ORD
-
JNB
32h 35m1 stop
R16 565British Airways
Sun, Feb 8 - Wed, Sep 23
KLM Logo
23:59 - 18:01
JNB
-
ORD
26h 02m2 stops
KLM Logo
12:29 - 22:05
ORD
-
JNB
25h 36m2 stops
R16 730KLM
Sun, Feb 22 - Sun, Mar 1
KLM Logo
23:45 - 22:33
CPT
-
MDW
30h 48m2 stops
KLM Logo
10:49 - 21:55
MDW
-
CPT
27h 06m2 stops
R20 892KLM
Mon, Feb 23 - Mon, Mar 2
Emirates Logo
19:10 - 15:45
DUR
-
ORD
27h 35m1 stop
Emirates Logo
20:35 - 16:35
ORD
-
DUR
37h 00m1 stop
R22 163Emirates
Fri, Mar 20 - Fri, Jun 26
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m1 stop
R23 402Emirates
Thu, Feb 19 - Mon, Feb 23

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 10 January 2026.
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

Fri 13/3

19:05-19:25

1 stop31h 20m

Chicago O'Hare Intl

Wed 15/4

20:10-10:30

1 stop31h 20m

R13 939

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 2/4

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Fri 10/4

10:15-14:35

1 stop21h 20m

R14 764

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 22/2

19:05-18:25

1 stop31h 20m

Chicago O'Hare Intl

Sun 1/3

20:20-10:50

1 stop30h 30m

R14 830

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 30/1

20:50-18:37

1 stop29h 47m

Chicago O'Hare Intl

Fri 6/2

18:17-16:10

1 stop37h 53m

R15 755

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 8/2

22:00-13:15

2 stops23h 15m

Chicago O'Hare Intl

Wed 23/9

9:25-18:30

2 stops26h 05m

R16 284

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 8/2

22:00-17:42

2 stops27h 42m

Chicago O'Hare Intl

Wed 23/9

17:50-9:25

1 stop32h 35m

R16 565

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 22/2

23:59-18:01

2 stops26h 02m

Chicago O'Hare Intl

Sun 1/3

12:29-22:05

2 stops25h 36m

R16 730

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Mon 23/2

23:45-22:33

2 stops30h 48m

Chicago Midway

Mon 2/3

10:49-21:55

2 stops27h 06m

R20 892

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Fri 20/3

19:10-15:45

1 stop27h 35m

Chicago O'Hare Intl

Fri 26/6

20:35-16:35

1 stop37h 00m

R22 163

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

R23 402

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 755. 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 465.

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 R17 752 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 152 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 826

Best Round-Trip Price

R13 939

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 R9 826 (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 939 (Johannesburg OR Tambo 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).
Search Deals
March has the highest demand for flights to Chicago, with a 8% 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 690.

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 586. 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 January 2026, 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 R875
Durban King Shaka Intl to Chicago Flightsfrom R1 035
Cape Town Intl to Chicago Flightsfrom R936