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Flights to Chicago

R9 273 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 1/6. 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 - 8:35
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
14:00 - 7:10
ORD
-
JNB
58h 10m
2 stops
R13 893Etihad Airways
Sun, Apr 5 - Sun, Apr 12
Turkish Airlines Logo
18:00 - 9:40
JNB
-
ORD
22h 40m
1 stop
Turkish Airlines Logo
11:25 - 10:30
ORD
-
JNB
40h 05m
1 stop
R14 279Turkish Airlines
Mon, Apr 6 - Mon, Apr 13
Ethiopian Air Logo
13:50 - 8:15
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 - 14:35
ORD
-
CPT
21h 20m
1 stop
R15 438Ethiopian Air
Sat, Apr 4 - Sat, Apr 11
Turkish Airlines Logo
19:05 - 11:05
JNB
-
ORD
23h 00m
1 stop
Turkish Airlines Logo
20:20 - 10:50
ORD
-
JNB
30h 30m
1 stop
R15 857Turkish Airlines
Wed, Mar 11 - Thu, Jan 14
United Airlines Logo
10:25 - 10:51
JNB
-
ORD
31h 26m
2 stops
United Airlines Logo
15:45 - 18:35
ORD
-
JNB
18h 50m
1 stop
R16 147United Airlines
Wed, Mar 11 - Thu, Jan 14
Ethiopian Air Logo
5:30 - 8:15
JNB
-
ORD
33h 45m
3 stops
Ethiopian Air Logo
10:15 - 20:10
ORD
-
JNB
26h 55m
1 stop
R16 758Ethiopian Air
Sun, Apr 5 - Sun, Apr 12
United Airlines Logo
20:00 - 18:50
CPT
-
ORD
29h 50m
1 stop
United Airlines Logo
21:21 - 15:20
ORD
-
CPT
58h 59m
2 stops
R17 338United Airlines
Tue, Jul 14 - Thu, Jul 30
KLM Logo
23:15 - 14:15
CPT
-
ORD
22h 00m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R17 966KLM
Thu, May 28 - Thu, Jun 4
KLM Logo
23:15 - 14:15
CPT
-
ORD
22h 00m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R18 062KLM
Thu, May 28 - Thu, Jun 4
Emirates Logo
18:40 - 15:45
DUR
-
ORD
28h 05m
1 stop
Emirates Logo
20:35 - 16:35
ORD
-
DUR
37h 00m
1 stop
R22 151Emirates
Sat, Apr 4 - Sat, Apr 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 21 February 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

Sun 5/4

9:50-8:35

1 stop29h 45m

Chicago O'Hare Intl

Sun 12/4

14:00-7:10

2 stops58h 10m

R13 893

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 6/4

18:00-9:40

1 stop22h 40m

Chicago O'Hare Intl

Mon 13/4

11:25-10:30

1 stop40h 05m

R14 279

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sat 4/4

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Sat 11/4

10:15-14:35

1 stop21h 20m

R15 438

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 11/3

19:05-11:05

1 stop23h 00m

Chicago O'Hare Intl

Thu 14/1

20:20-10:50

1 stop30h 30m

R15 857

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 11/3

10:25-10:51

2 stops31h 26m

Chicago O'Hare Intl

Thu 14/1

15:45-18:35

1 stop18h 50m

R16 147

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 5/4

5:30-8:15

3 stops33h 45m

Chicago O'Hare Intl

Sun 12/4

10:15-20:10

1 stop26h 55m

R16 758

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 14/7

20:00-18:50

1 stop29h 50m

Chicago O'Hare Intl

Thu 30/7

21:21-15:20

2 stops58h 59m

R17 338

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 28/5

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

Thu 4/6

16:20-21:25

1 stop22h 05m

R17 966

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 28/5

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

Thu 4/6

16:20-21:25

1 stop22h 05m

R18 062

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sat 4/4

18:40-15:45

1 stop28h 05m

Chicago O'Hare Intl

Sat 11/4

20:35-16:35

1 stop37h 00m

R22 151

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 261. 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 R15 970.

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 746 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 326 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 273

Best Round-Trip Price

R13 893

Fastest flight time

28h 36m

Popular in

November
The best one-way flight price to Chicago from South Africa in the last 72 hours is R9 273 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from South Africa in the last 72 hours is R13 893 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 28h 36m (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
November 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 374.

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 371. 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 February 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
Cape Town Intl to Chicago Flightsfrom R934
Johannesburg to Chicago Flightsfrom R863
Durban King Shaka Intl to Chicago Flightsfrom R1 186