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Flights to Chicago

R9 588 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 19/5. 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 - 8:20
ORD
-
JNB
35h 20m
1 stop
R13 155Etihad Airways
Thu, Mar 19 - Thu, Apr 2
Ethiopian Air Logo
14:30 - 8:40
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 - 13:05
ORD
-
JNB
19h 50m
1 stop
R13 283Ethiopian Air
Wed, Mar 11 - Mon, Mar 23
Ethiopian Air Logo
14:30 - 8:40
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 - 13:05
ORD
-
JNB
19h 50m
1 stop
R13 426Ethiopian Air
Tue, Mar 10 - Mon, Mar 23
Ethiopian Air Logo
8:20 - 7:40
JNB
-
ORD
31h 20m
2 stops
Ethiopian Air Logo
10:15 - 13:05
ORD
-
JNB
19h 50m
1 stop
R13 522Ethiopian Air
Wed, Feb 25 - Mon, Mar 16
Etihad Airways Logo
9:50 - 7:35
JNB
-
ORD
29h 45m
1 stop
Etihad Airways Logo
14:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R14 302Etihad Airways
Wed, Feb 25 - Mon, Mar 16
Virgin Atlantic Logo
22:00 - 22:31
JNB
-
MDW
32h 31m
2 stops
Virgin Atlantic Logo
12:47 - 19:00
MDW
-
JNB
23h 13m
1 stop
R15 990Virgin Atlantic
Wed, Feb 25 - Mon, Mar 16
Delta Logo
22:00 - 18:40
JNB
-
MDW
27h 40m
2 stops
Delta Logo
10:45 - 19:00
MDW
-
JNB
25h 15m
1 stop
R16 197Delta
Wed, Mar 11 - Mon, Mar 23
Delta Logo
21:30 - 18:40
JNB
-
MDW
29h 10m
2 stops
Delta Logo
9:35 - 19:40
MDW
-
JNB
27h 05m
2 stops
R16 213Delta
Thu, Mar 5 - Fri, Apr 3
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 854KLM
Thu, May 28 - Thu, Jun 4
KLM Logo
23:15 - 17:56
CPT
-
MDW
25h 41m
2 stops
KLM Logo
12:51 - 21:25
MDW
-
CPT
25h 34m
2 stops
R28 254KLM
Thu, May 28 - Thu, Jun 4

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 15 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

Thu 19/3

9:50-8:35

1 stop29h 45m

Chicago O'Hare Intl

Thu 2/4

14:00-8:20

1 stop35h 20m

R13 155

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 11/3

14:30-8:40

2 stops25h 10m

Chicago O'Hare Intl

Mon 23/3

10:15-13:05

1 stop19h 50m

R13 283

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 10/3

14:30-8:40

2 stops25h 10m

Chicago O'Hare Intl

Mon 23/3

10:15-13:05

1 stop19h 50m

R13 426

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 25/2

8:20-7:40

2 stops31h 20m

Chicago O'Hare Intl

Mon 16/3

10:15-13:05

1 stop19h 50m

R13 522

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 25/2

9:50-7:35

1 stop29h 45m

Chicago O'Hare Intl

Mon 16/3

14:10-8:20

1 stop35h 10m

R14 302

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Wed 25/2

22:00-22:31

2 stops32h 31m

Chicago Midway

Mon 16/3

12:47-19:00

1 stop23h 13m

R15 990

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Wed 11/3

22:00-18:40

2 stops27h 40m

Chicago Midway

Mon 23/3

10:45-19:00

1 stop25h 15m

R16 197

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 5/3

21:30-18:40

2 stops29h 10m

Chicago Midway

Fri 3/4

9:35-19:40

2 stops27h 05m

R16 213

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 854

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 28/5

23:15-17:56

2 stops25h 41m

Chicago Midway

Thu 4/6

12:51-21:25

2 stops25h 34m

R28 254

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 098. 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 799.

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 550 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 066 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 588

Best Round-Trip Price

R13 155

Fastest flight time

24h 05m

Popular in

November
The best one-way flight price to Chicago from South Africa in the last 72 hours is R9 588 (Cape Town Intl 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 155 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 24h 05m (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
November has the highest demand for flights to Chicago, with a 9% 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 186.

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 403. 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 27,7 km away - Chicago’s Chicago O'Hare Intl 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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Popular Flights to Chicago

Popular routes according to searches in the past day on momondo
Cape Town Intl to Chicago Flightsfrom R917
Johannesburg to Chicago Flightsfrom R834
Durban King Shaka Intl to Chicago Flightsfrom R1 084