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Flights to Chicago

R9 959 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
13:50 - 8:15
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 - 14:10
ORD
-
CPT
20h 55m
1 stop
R15 560Ethiopian Air
Fri, Sep 11 - Sun, Sep 27
Delta Logo
20:05 - 23:57
CPT
-
ORD
34h 52m
1 stop
Delta Logo
15:40 - 17:50
ORD
-
CPT
19h 10m
1 stop
R16 040Delta
Tue, Aug 11 - Mon, Sep 21
Virgin Atlantic Logo
20:05 - 16:51
CPT
-
ORD
27h 46m
1 stop
Virgin Atlantic Logo
18:25 - 17:50
ORD
-
CPT
40h 25m
1 stop
R16 173Virgin Atlantic
Sun, Aug 16 - Sun, Aug 23
United Airlines Logo
22:00 - 21:18
JNB
-
ORD
31h 18m
1 stop
United Airlines Logo
21:47 - 18:35
ORD
-
JNB
36h 48m
2 stops
R16 554United Airlines
Thu, Nov 12 - Tue, Nov 24
United Airlines Logo
19:50 - 13:13
CPT
-
ORD
24h 23m
2 stops
United Airlines Logo
10:25 - 15:20
ORD
-
CPT
21h 55m
2 stops
R16 654United Airlines
Thu, Aug 20 - Thu, Aug 27
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
21:10 - 8:20
ORD
-
JNB
28h 10m
1 stop
R16 736Etihad Airways
Wed, Aug 26 - Tue, Sep 29
KLM Logo
23:15 - 14:30
CPT
-
ORD
22h 15m
1 stop
KLM Logo
16:20 - 21:10
ORD
-
CPT
21h 50m
1 stop
R16 753KLM
Sun, Sep 6 - Sun, Sep 13
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 803KLM
Fri, Sep 11 - Sun, Sep 27
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
14:00 - 8:20
ORD
-
JNB
35h 20m
1 stop
R16 952Etihad Airways
Wed, Sep 9 - Mon, Sep 21
British Airways Logo
11:15 - 18:45
DUR
-
ORD
39h 30m
2 stops
British Airways Logo
20:40 - 10:40
ORD
-
DUR
54h 00m
2 stops
R18 012British Airways
Wed, Dec 2 - Thu, Jan 21

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 24 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 11/9

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Sun 27/9

10:15-14:10

1 stop20h 55m

R15 560

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 11/8

20:05-23:57

1 stop34h 52m

Chicago O'Hare Intl

Mon 21/9

15:40-17:50

1 stop19h 10m

R16 040

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sun 16/8

20:05-16:51

1 stop27h 46m

Chicago O'Hare Intl

Sun 23/8

18:25-17:50

1 stop40h 25m

R16 173

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 12/11

22:00-21:18

1 stop31h 18m

Chicago O'Hare Intl

Tue 24/11

21:47-18:35

2 stops36h 48m

R16 554

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 20/8

19:50-13:13

2 stops24h 23m

Chicago O'Hare Intl

Thu 27/8

10:25-15:20

2 stops21h 55m

R16 654

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 26/8

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Tue 29/9

21:10-8:20

1 stop28h 10m

R16 736
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sun 6/9

23:15-14:30

1 stop22h 15m

Chicago O'Hare Intl

Sun 13/9

16:20-21:10

1 stop21h 50m

R16 753

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 803

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 9/9

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Mon 21/9

14:00-8:20

1 stop35h 20m

R16 952

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Wed 2/12

11:15-18:45

2 stops39h 30m

Chicago O'Hare Intl

Thu 21/1

20:40-10:40

2 stops54h 00m

R18 012

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 September is, on average, the cheapest month to fly to Chicago from South Africa, with most prices found around R15 958. If you are unable to visit Chicago during the month of September, then departing from South Africa during the month February is also very affordable. Most momondo users find prices during this month for around R16 123.

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 643 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 494 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 959

Best Round-Trip Price

R15 560

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 959 (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 560 (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 12% 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 348.

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 590. 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 R946
Cape Town Intl to Chicago Flightsfrom R994
Durban King Shaka Intl to Chicago Flightsfrom R1 087