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Flights to Chicago

R9 345 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 13/7. 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.
KLM Logo
7:40 - 14:15
CPT
-
ORD
37h 35m
1 stop
KLM Logo
16:25 - 22:40
ORD
-
CPT
22h 15m
1 stop
R16 224KLM
Fri, Oct 9 - Sat, Nov 14
KLM Logo
23:15 - 21:32
CPT
-
ORD
29h 17m
2 stops
KLM Logo
16:25 - 22:40
ORD
-
CPT
22h 15m
1 stop
R16 386KLM
Fri, Oct 9 - Sat, Nov 14
United Airlines Logo
20:00 - 14:26
CPT
-
ORD
25h 26m
1 stop
United Airlines Logo
6:25 - 16:10
ORD
-
CPT
25h 45m
1 stop
R16 418United Airlines
Fri, Oct 9 - Sat, Nov 14
United Airlines Logo
20:00 - 9:38
CPT
-
ORD
20h 38m
1 stop
United Airlines Logo
10:00 - 16:10
ORD
-
CPT
22h 10m
2 stops
R16 483United Airlines
Fri, Oct 9 - Sat, Nov 14
United Airlines Logo
20:00 - 12:54
CPT
-
ORD
23h 54m
2 stops
United Airlines Logo
10:00 - 16:10
ORD
-
CPT
22h 10m
2 stops
R16 500United Airlines
Fri, Oct 9 - Sat, Nov 14
Turkish Airlines Logo
18:50 - 11:00
JNB
-
ORD
24h 10m
1 stop
Turkish Airlines Logo
11:45 - 22:25
ORD
-
JNB
26h 40m
1 stop
R16 792Turkish Airlines
Sun, Nov 1 - Tue, Nov 17
Ethiopian Air Logo
8:20 - 8:15
JNB
-
ORD
30h 55m
2 stops
Ethiopian Air Logo
10:15 - 3:55
ORD
-
JNB
34h 40m
1 stop
R16 986Ethiopian Air
Sat, Sep 12 - Sat, Oct 17
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
13:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R17 181Etihad Airways
Mon, Sep 7 - Wed, Mar 3
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
9:42 - 8:20
ORD
-
JNB
39h 38m
2 stops
R17 635Etihad Airways
Mon, Jul 27 - Mon, Aug 10
British Airways Logo
11:15 - 12:30
DUR
-
ORD
32h 15m
2 stops
British Airways Logo
19:05 - 10:40
ORD
-
DUR
32h 35m
2 stops
R84 039British Airways
Fri, Jul 24 - Mon, Aug 10

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 5 July 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

Fri 9/10

7:40-14:15

1 stop37h 35m

Chicago O'Hare Intl

Sat 14/11

16:25-22:40

1 stop22h 15m

R16 224

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 9/10

23:15-21:32

2 stops29h 17m

Chicago O'Hare Intl

Sat 14/11

16:25-22:40

1 stop22h 15m

R16 386

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 9/10

20:00-14:26

1 stop25h 26m

Chicago O'Hare Intl

Sat 14/11

6:25-16:10

1 stop25h 45m

R16 418
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 9/10

20:00-9:38

1 stop20h 38m

Chicago O'Hare Intl

Sat 14/11

10:00-16:10

2 stops22h 10m

R16 483

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 9/10

20:00-12:54

2 stops23h 54m

Chicago O'Hare Intl

Sat 14/11

10:00-16:10

2 stops22h 10m

R16 500

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 1/11

18:50-11:00

1 stop24h 10m

Chicago O'Hare Intl

Tue 17/11

11:45-22:25

1 stop26h 40m

R16 792

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sat 12/9

8:20-8:15

2 stops30h 55m

Chicago O'Hare Intl

Sat 17/10

10:15-3:55

1 stop34h 40m

R16 986

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 7/9

9:45-8:35

1 stop29h 50m

Chicago O'Hare Intl

Wed 3/3

13:10-8:20

1 stop35h 10m

R17 181

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 27/7

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Mon 10/8

9:42-8:20

2 stops39h 38m

R17 635

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Fri 24/7

11:15-12:30

2 stops32h 15m

Chicago O'Hare Intl

Mon 10/8

19:05-10:40

2 stops32h 35m

R84 039

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 380. If you are unable to visit Chicago during the month of February, then departing from South Africa during the month October is also very affordable. Most momondo users find prices during this month for around R15 477.

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 078 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 169 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 345

Best Round-Trip Price

R16 224

Fastest flight time

25h 10m

Popular in

January
The best one-way flight price to Chicago from South Africa in the last 5 days is R9 345 (Johannesburg OR Tambo 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 224 (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 25h 10m (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
January has the highest demand for flights to Chicago, with a 8% 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 R17 989.

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 427. 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 July 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 R948
Cape Town Intl to Chicago Flightsfrom R1 012
Durban King Shaka Intl to Chicago Flightsfrom R1 086