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Flights to Chicago

R9 913 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-
25h 25m
Ethiopian Air Logo
10:15 - 14:10-
20h 55m
R14 696Ethiopian Air
Wed, Sep 23 - Wed, Sep 30
Ethiopian Air Logo
13:50 - 8:15-
25h 25m
Ethiopian Air Logo
10:15 - 14:10-
20h 55m
R15 487Ethiopian Air
Fri, Sep 11 - Sun, Sep 27
Virgin Atlantic Logo
22:00 - 17:20-
27h 20m
Virgin Atlantic Logo
13:30 - 12:05-
38h 35m
R16 296Virgin Atlantic
Fri, Dec 4 - Tue, Jan 12
KLM Logo
23:00 - 14:15-
22h 15m
KLM Logo
16:50 - 5:50-
30h 00m
R16 461KLM
Mon, Aug 31 - Mon, Sep 7
Delta Logo
20:50 - 10:19-
21h 29m
Delta Logo
9:30 - 18:35-
25h 05m
R16 477Delta
Sun, Dec 6 - Wed, Jan 13
United Airlines Logo
22:00 - 18:32-
27h 32m
United Airlines Logo
12:45 - 18:30-
22h 45m
R16 543United Airlines
Sun, Sep 13 - Sun, Sep 20
United Airlines Logo
22:00 - 16:34-
25h 34m
United Airlines Logo
12:16 - 18:30-
23h 14m
R16 543United Airlines
Sun, Sep 13 - Sun, Sep 20
KLM Logo
23:00 - 20:30-
28h 30m
KLM Logo
16:50 - 21:25-
21h 35m
R16 609KLM
Mon, Aug 31 - Mon, Sep 7
Turkish Airlines Logo
18:50 - 10:00-
23h 10m
Turkish Airlines Logo
11:45 - 11:00-
39h 15m
R16 708Turkish Airlines
Wed, Dec 2 - Mon, Jan 11
Turkish Airlines Logo
18:50 - 18:20-
31h 30m
Turkish Airlines Logo
20:15 - 11:00-
30h 45m
R16 708Turkish Airlines
Wed, Dec 2 - Wed, Jan 13

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 4 August 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 - ORD

CPTORD

Cape Town Intl

Wed 23/9

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Wed 30/9

10:15-14:10

1 stop20h 55m

R14 696

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 487

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 4/12

22:00-17:20

2 stops27h 20m

Chicago O'Hare Intl

Tue 12/1

13:30-12:05

2 stops38h 35m

R16 296

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 31/8

23:00-14:15

1 stop22h 15m

Chicago O'Hare Intl

Mon 7/9

16:50-5:50

1 stop30h 00m

R16 460

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sun 6/12

20:50-10:19

1 stop21h 29m

Chicago O'Hare Intl

Wed 13/1

9:30-18:35

1 stop25h 05m

R16 477

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 13/9

22:00-18:32

2 stops27h 32m

Chicago O'Hare Intl

Sun 20/9

12:45-18:30

2 stops22h 45m

R16 543

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 13/9

22:00-16:34

1 stop25h 34m

Chicago O'Hare Intl

Sun 20/9

12:16-18:30

1 stop23h 14m

R16 543

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 31/8

23:00-20:30

2 stops28h 30m

Chicago O'Hare Intl

Mon 7/9

16:50-21:25

1 stop21h 35m

R16 609

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 2/12

18:50-10:00

1 stop23h 10m

Chicago O'Hare Intl

Mon 11/1

11:45-11:00

1 stop39h 15m

R16 708

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 2/12

18:50-18:20

1 stop31h 30m

Chicago O'Hare Intl

Wed 13/1

20:15-11:00

1 stop30h 45m

R16 708

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 R16 048. 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 R16 048.

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 465 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 421 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 913

Best Round-Trip Price

R14 696

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 913 (Durban King Shaka Intl to Chicago O'Hare Intl).
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The best return flight price to Chicago from South Africa in the last 5 days is R14 696 (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 14% 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 70 days out, which is when prices tend to be around R18 261.

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 558. 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 August 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 R941
Cape Town Intl to Chicago Flightsfrom R891
Durban King Shaka Intl to Chicago Flightsfrom R1 084