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Flights to Chicago

R9 485 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 27/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 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.
Ethiopian Air Logo
13:50 - 8:15
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 - 14:10
ORD
-
CPT
20h 55m
1 stop
R14 509Ethiopian Air
Wed, Sep 23 - Wed, Sep 30
Ethiopian Air Logo
13:50 - 8:15
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 - 14:10
ORD
-
CPT
20h 55m
1 stop
R14 641Ethiopian Air
Wed, Sep 23 - Wed, Sep 30
Delta Logo
20:05 - 12:39
CPT
-
MDW
23h 34m
2 stops
Delta Logo
12:46 - 17:50
MDW
-
CPT
22h 04m
1 stop
R15 765Delta
Tue, Aug 11 - Mon, Aug 17
Delta Logo
20:05 - 12:39
CPT
-
MDW
23h 34m
2 stops
Delta Logo
9:24 - 17:50
MDW
-
CPT
25h 26m
2 stops
R15 765Delta
Tue, Aug 11 - Thu, Aug 20
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
21:10 - 8:15
ORD
-
JNB
28h 05m
1 stop
R16 525Etihad Airways
Thu, Sep 10 - Thu, Sep 17
United Airlines Logo
22:00 - 21:00
JNB
-
ORD
30h 00m
1 stop
United Airlines Logo
15:00 - 18:30
ORD
-
JNB
20h 30m
1 stop
R16 542United Airlines
Mon, Sep 14 - Sun, Sep 27
United Airlines Logo
22:00 - 14:20
JNB
-
ORD
23h 20m
2 stops
United Airlines Logo
10:50 - 18:30
ORD
-
JNB
24h 40m
2 stops
R16 558United Airlines
Sun, Sep 13 - Sun, Sep 20
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
21:20 - 8:20
ORD
-
JNB
28h 00m
1 stop
R16 641Etihad Airways
Thu, Sep 3 - Thu, Oct 29
Turkish Airlines Logo
15:45 - 10:00
DUR
-
ORD
26h 15m
2 stops
Turkish Airlines Logo
11:45 - 13:45
ORD
-
DUR
42h 00m
2 stops
R16 657Turkish Airlines
Sun, Nov 15 - Fri, Nov 20
Turkish Airlines Logo
17:55 - 9:40
JNB
-
ORD
22h 45m
1 stop
Turkish Airlines Logo
20:10 - 10:15
ORD
-
JNB
31h 05m
1 stop
R16 723Turkish Airlines
Thu, Oct 1 - Tue, Oct 6

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 1 August 2026.
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 23/9

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Wed 30/9

10:15-14:10

1 stop20h 55m

R14 509

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 23/9

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Wed 30/9

10:15-14:10

1 stop20h 55m

R14 641
Fastest return journey

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Tue 11/8

20:05-12:39

2 stops23h 34m

Chicago Midway

Mon 17/8

12:46-17:50

1 stop22h 04m

R15 765

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Tue 11/8

20:05-12:39

2 stops23h 34m

Chicago Midway

Thu 20/8

9:24-17:50

2 stops25h 26m

R15 765

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 10/9

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Thu 17/9

21:10-8:15

1 stop28h 05m

R16 525

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 14/9

22:00-21:00

1 stop30h 00m

Chicago O'Hare Intl

Sun 27/9

15:00-18:30

1 stop20h 30m

R16 542

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 13/9

22:00-14:20

2 stops23h 20m

Chicago O'Hare Intl

Sun 20/9

10:50-18:30

2 stops24h 40m

R16 558

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 3/9

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Thu 29/10

21:20-8:20

1 stop28h 00m

R16 641

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sun 15/11

15:45-10:00

2 stops26h 15m

Chicago O'Hare Intl

Fri 20/11

11:45-13:45

2 stops42h 00m

R16 657

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 1/10

17:55-9:40

1 stop22h 45m

Chicago O'Hare Intl

Tue 6/10

20:10-10:15

1 stop31h 05m

R16 723

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 R16 079. 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 079.

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 R19 502 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 R15 451 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 485

Best Round-Trip Price

R14 509

Fastest flight time

25h 55m

Popular in

January
The best one-way flight price to Chicago from South Africa in the last 5 days is R9 485 (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
The best return flight price to Chicago from South Africa in the last 5 days is R14 509 (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 25h 55m (Durban King Shaka Intl to Chicago O'Hare Intl).
Search Deals
January has the highest demand for flights to Chicago, with a 14% price increase on average.
Search Deals

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 70 days out, which is when prices tend to be around R18 296.

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 R3 580. Users typically find the best prices when using momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Grand Boulevard?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Grand Boulevard (11,0 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 August 2026, there are 9 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 R899
Cape Town Intl to Chicago Flightsfrom R886
Durban King Shaka Intl to Chicago Flightsfrom R1 029