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Flights to Chicago

R9 792 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.
Delta Logo
20:05 - 12:39
CPT
-
MDW
23h 34m
2 stops
Delta Logo
17:10 - 17:50
MDW
-
CPT
17h 40m
1 stop
R15 876Delta
mar., ago. 25 - lun., sep. 7
Delta Logo
20:05 - 9:23
CPT
-
ORD
20h 18m
1 stop
Delta Logo
18:25 - 17:50
ORD
-
CPT
40h 25m
1 stop
R15 876Delta
mar., ago. 25 - mié., sep. 9
Delta Logo
20:05 - 12:39
CPT
-
MDW
23h 34m
2 stops
Delta Logo
17:45 - 17:50
MDW
-
CPT
41h 05m
2 stops
R15 990Delta
mar., ago. 25 - dom., sep. 6
KLM Logo
23:15 - 14:15
CPT
-
ORD
22h 00m
1 stop
KLM Logo
13:29 - 21:25
ORD
-
CPT
24h 56m
2 stops
R16 071KLM
mié., ago. 26 - mié., sep. 9
KLM Logo
15:20 - 14:30
CPT
-
ORD
30h 10m
2 stops
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 169KLM
mar., ago. 4 - mar., ago. 11
United Airlines Logo
19:50 - 12:59
CPT
-
ORD
24h 09m
1 stop
United Airlines Logo
14:32 - 17:10
ORD
-
CPT
19h 38m
1 stop
R16 331United Airlines
jue., ago. 20 - dom., sep. 13
United Airlines Logo
20:00 - 14:29
CPT
-
ORD
25h 29m
1 stop
United Airlines Logo
21:39 - 15:20
ORD
-
CPT
34h 41m
1 stop
R16 397United Airlines
dom., ago. 2 - mié., ago. 12
Emirates Logo
18:40 - 15:45
DUR
-
ORD
28h 05m
1 stop
Emirates Logo
20:35 - 16:35
ORD
-
DUR
37h 00m
1 stop
R20 854Emirates
lun., ago. 31 - dom., sep. 13
Qatar Airways Logo
12:05 - 15:05
DUR
-
ORD
34h 00m
2 stops
Qatar Airways Logo
19:20 - 17:40
ORD
-
DUR
39h 20m
2 stops
R21 374Qatar Airways
lun., ago. 31 - dom., sep. 13
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m
1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m
1 stop
R29 930Emirates
mié., dic. 16 - dom., ene. 3

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 13 julio 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
Fastest return journey

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

mar. 25/8

20:05-12:39

2 stops23h 34m

Chicago Midway

lun. 7/9

17:10-17:50

1 stop17h 40m

R15 876

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

mar. 25/8

20:05-9:23

1 stop20h 18m

Chicago O'Hare Intl

mié. 9/9

18:25-17:50

1 stop40h 25m

R15 876

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

mar. 25/8

20:05-12:39

2 stops23h 34m

Chicago Midway

dom. 6/9

17:45-17:50

2 stops41h 05m

R15 990

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

mié. 26/8

23:15-14:15

1 stop22h 00m

Chicago O'Hare Intl

mié. 9/9

13:29-21:25

2 stops24h 56m

R16 071

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

mar. 4/8

15:20-14:30

2 stops30h 10m

Chicago O'Hare Intl

mar. 11/8

16:20-21:25

1 stop22h 05m

R16 169

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

jue. 20/8

19:50-12:59

1 stop24h 09m

Chicago O'Hare Intl

dom. 13/9

14:32-17:10

1 stop19h 38m

R16 331

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

dom. 2/8

20:00-14:29

1 stop25h 29m

Chicago O'Hare Intl

mié. 12/8

21:39-15:20

1 stop34h 41m

R16 397

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

lun. 31/8

18:40-15:45

1 stop28h 05m

Chicago O'Hare Intl

dom. 13/9

20:35-16:35

1 stop37h 00m

R20 854

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

lun. 31/8

12:05-15:05

2 stops34h 00m

Chicago O'Hare Intl

dom. 13/9

19:20-17:40

2 stops39h 20m

R21 374

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

mié. 16/12

19:10-14:55

1 stop27h 45m

Chicago O'Hare Intl

dom. 3/1

19:45-17:10

1 stop37h 25m

R29 930

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 421. 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 583.

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 220 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 209 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 792

Best Round-Trip Price

R15 876

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 792 (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 876 (Cape Town Intl to Chicago Midway).
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 R17 931.

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 487. 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 R983
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Cape Town Intl to Chicago Flightsfrom R969