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Flights to Chicago

R9 925 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 5/10. 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.
Ethiopian Air Logo
15:25 - 7:40
CPT
-
ORD
48h 15m
2 stops
Ethiopian Air Logo
9:45 - 13:00
ORD
-
CPT
43h 15m
1 stop
R15 284Ethiopian Air
Fri, Nov 27 - Fri, Dec 4
Virgin Atlantic Logo
20:05 - 23:57
CPT
-
ORD
34h 52m
1 stop
Virgin Atlantic Logo
18:25 - 17:50
ORD
-
CPT
40h 25m
1 stop
R15 943Virgin Atlantic
Sun, Aug 2 - Wed, Aug 12
KLM Logo
23:00 - 14:15
CPT
-
ORD
22h 15m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 372KLM
Mon, Aug 3 - Tue, Aug 25
United Airlines Logo
22:00 - 14:26
JNB
-
ORD
23h 26m
2 stops
United Airlines Logo
12:55 - 18:30
ORD
-
JNB
22h 35m
2 stops
R16 520United Airlines
Thu, Oct 1 - Tue, Oct 13
United Airlines Logo
19:50 - 14:21
CPT
-
ORD
25h 31m
2 stops
United Airlines Logo
11:15 - 17:10
ORD
-
CPT
22h 55m
2 stops
R16 520United Airlines
Thu, Aug 27 - Wed, Sep 9
United Airlines Logo
19:50 - 13:08
CPT
-
ORD
24h 18m
1 stop
United Airlines Logo
6:30 - 15:20
ORD
-
CPT
25h 50m
1 stop
R16 553United Airlines
Sat, Aug 1 - Sat, Aug 15
United Airlines Logo
19:50 - 13:15
CPT
-
ORD
24h 25m
2 stops
United Airlines Logo
21:35 - 17:10
ORD
-
CPT
36h 35m
2 stops
R16 619United Airlines
Mon, Aug 3 - Tue, Aug 25
KLM Logo
7:40 - 14:15
CPT
-
ORD
37h 35m
1 stop
KLM Logo
16:20 - 21:10
ORD
-
CPT
21h 50m
1 stop
R16 702KLM
Fri, Sep 11 - Sun, Sep 27
Turkish Airlines Logo
18:00 - 18:15
JNB
-
ORD
31h 15m
1 stop
Turkish Airlines Logo
21:15 - 22:25
ORD
-
JNB
42h 10m
1 stop
R16 867Turkish Airlines
Fri, Oct 16 - Fri, Oct 30
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
14:00 - 8:20
ORD
-
JNB
35h 20m
1 stop
R16 883Etihad Airways
Mon, Aug 3 - Mon, Aug 24

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 18 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 27/11

15:25-7:40

2 stops48h 15m

Chicago O'Hare Intl

Fri 4/12

9:45-13:00

1 stop43h 15m

R15 284

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sun 2/8

20:05-23:57

1 stop34h 52m

Chicago O'Hare Intl

Wed 12/8

18:25-17:50

1 stop40h 25m

R15 943
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 3/8

23:00-14:15

1 stop22h 15m

Chicago O'Hare Intl

Tue 25/8

16:20-21:25

1 stop22h 05m

R16 372

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 1/10

22:00-14:26

2 stops23h 26m

Chicago O'Hare Intl

Tue 13/10

12:55-18:30

2 stops22h 35m

R16 520

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 27/8

19:50-14:21

2 stops25h 31m

Chicago O'Hare Intl

Wed 9/9

11:15-17:10

2 stops22h 55m

R16 520

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sat 1/8

19:50-13:08

1 stop24h 18m

Chicago O'Hare Intl

Sat 15/8

6:30-15:20

1 stop25h 50m

R16 553

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 3/8

19:50-13:15

2 stops24h 25m

Chicago O'Hare Intl

Tue 25/8

21:35-17:10

2 stops36h 35m

R16 619

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 11/9

7:40-14:15

1 stop37h 35m

Chicago O'Hare Intl

Sun 27/9

16:20-21:10

1 stop21h 50m

R16 702

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 16/10

18:00-18:15

1 stop31h 15m

Chicago O'Hare Intl

Fri 30/10

21:15-22:25

1 stop42h 10m

R16 867

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 3/8

9:45-8:35

1 stop29h 50m

Chicago O'Hare Intl

Mon 24/8

14:00-8:20

1 stop35h 20m

R16 883

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 630. 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 795.

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 481 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 416 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 925

Best Round-Trip Price

R15 284

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 925 (Durban King Shaka Intl to Chicago O'Hare Intl).
Search Deals
The best return flight price to Chicago from South Africa in the last 5 days is R15 284 (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 7% 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 175.

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 534. 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.

An easier way to manage your Chicago trip

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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 R987
Cape Town Intl to Chicago Flightsfrom R932
Durban King Shaka Intl to Chicago Flightsfrom R1 203