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Flights to Chicago

R9 841 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 11/10. 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.
Delta Logo
20:05 - 22:15
CPT
-
MDW
33h 10m
1 stop
Delta Logo
10:54 - 17:50
MDW
-
CPT
23h 56m
1 stop
R16 562Delta
Sun, Jul 19 - Mon, Aug 10
Delta Logo
20:05 - 23:53
CPT
-
ORD
34h 48m
1 stop
Delta Logo
19:25 - 17:50
ORD
-
CPT
39h 25m
2 stops
R16 562Delta
Sun, Jul 19 - Sun, Aug 9
KLM Logo
23:15 - 14:15
CPT
-
ORD
22h 00m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 744KLM
Mon, Jul 20 - Tue, Aug 11
United Airlines Logo
20:00 - 23:31
CPT
-
ORD
34h 31m
1 stop
United Airlines Logo
21:30 - 17:10
ORD
-
CPT
36h 40m
1 stop
R16 777United Airlines
Fri, Jul 10 - Tue, Jul 28
KLM Logo
23:15 - 14:15
CPT
-
ORD
22h 00m
1 stop
KLM Logo
14:12 - 21:25
ORD
-
CPT
24h 13m
2 stops
R16 826KLM
Mon, Jul 20 - Tue, Aug 11
United Airlines Logo
19:50 - 9:43
CPT
-
ORD
20h 53m
1 stop
United Airlines Logo
21:52 - 17:10
ORD
-
CPT
36h 18m
2 stops
R16 942United Airlines
Thu, Jun 18 - Tue, Oct 20
Etihad Airways Logo
21:45 - 15:40
JNB
-
ORD
48h 55m
2 stops
Etihad Airways Logo
20:25 - 8:20
ORD
-
JNB
28h 55m
1 stop
R17 123Etihad Airways
Fri, Jul 24 - Mon, Aug 24
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
20:25 - 8:20
ORD
-
JNB
28h 55m
1 stop
R17 289Etihad Airways
Sat, Jul 18 - Sat, Jul 25
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
17:10 - 10:40
ORD
-
DUR
57h 30m
2 stops
R19 699British Airways
Sun, Nov 8 - Thu, Nov 12
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
17:10 - 10:40
ORD
-
DUR
57h 30m
2 stops
R19 831British Airways
Sun, Nov 8 - Thu, Nov 12

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 6 June 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 - MDW

CPTMDW

Cape Town Intl

Sun 19/7

20:05-22:15

1 stop33h 10m

Chicago Midway

Mon 10/8

10:54-17:50

1 stop23h 56m

R16 562

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sun 19/7

20:05-23:53

1 stop34h 48m

Chicago O'Hare Intl

Sun 9/8

19:25-17:50

2 stops39h 25m

R16 562
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 20/7

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

Tue 11/8

16:20-21:25

1 stop22h 05m

R16 744

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 10/7

20:00-23:31

1 stop34h 31m

Chicago O'Hare Intl

Tue 28/7

21:30-17:10

1 stop36h 40m

R16 777

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 20/7

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

Tue 11/8

14:12-21:25

2 stops24h 13m

R16 826

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 18/6

19:50-9:43

1 stop20h 53m

Chicago O'Hare Intl

Tue 20/10

21:52-17:10

2 stops36h 18m

R16 942

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 24/7

21:45-15:40

2 stops48h 55m

Chicago O'Hare Intl

Mon 24/8

20:25-8:20

1 stop28h 55m

R17 123

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sat 18/7

9:45-8:35

1 stop29h 50m

Chicago O'Hare Intl

Sat 25/7

20:25-8:20

1 stop28h 55m

R17 289

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sun 8/11

11:15-13:50

2 stops34h 35m

Chicago O'Hare Intl

Thu 12/11

17:10-10:40

2 stops57h 30m

R19 699

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sun 8/11

11:15-13:50

2 stops34h 35m

Chicago O'Hare Intl

Thu 12/11

17:10-10:40

2 stops57h 30m

R19 831

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 R14 861. 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 067.

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 652 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 307 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 841

Best Round-Trip Price

R16 562

Fastest flight time

26h 35m

Popular in

January
The best one-way flight price to Chicago from South Africa in the last 5 days is R9 841 (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from South Africa in the last 5 days is R16 562 (Cape Town Intl to Chicago Midway).
Search Deals
The fastest flight to Chicago from South Africa takes 26h 35m (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
January 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 734.

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

Are there flights to Kenwood?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Kenwood (12,9 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 June 2026, there are 11 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 R967
Cape Town Intl to Chicago Flightsfrom R1 022
Durban King Shaka Intl to Chicago Flightsfrom R1 193