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Flights to Chicago

R9 930 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 7/4. 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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Find the cheapest flights from South Africa to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
14:00 - 8:15
ORD
-
JNB
35h 15m
1 stop
R14 181Etihad Airways
Wed, May 6 - Wed, May 13
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
14:00 - 8:15
ORD
-
JNB
35h 15m
1 stop
R14 385Etihad Airways
Sun, May 3 - Wed, May 20
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
R14 470Etihad Airways
Wed, Jun 3 - Tue, Jun 9
Ethiopian Air Logo
13:50 - 8:15
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 - 14:35
ORD
-
CPT
21h 20m
1 stop
R15 915Ethiopian Air
Wed, Apr 22 - Thu, Apr 30
Turkish Airlines Logo
16:35 - 18:15
CPT
-
ORD
32h 40m
1 stop
Turkish Airlines Logo
11:25 - 11:50
ORD
-
CPT
41h 25m
1 stop
R16 170Turkish Airlines
Wed, Jul 15 - Wed, Aug 19
Ethiopian Air Logo
13:50 - 8:15
CPT
-
ORD
25h 25m
2 stops
Ethiopian Air Logo
10:15 - 14:35
ORD
-
CPT
21h 20m
1 stop
R16 884Ethiopian Air
Wed, Apr 22 - Sun, May 3
Turkish Airlines Logo
16:35 - 9:40
CPT
-
ORD
24h 05m
1 stop
Turkish Airlines Logo
20:20 - 11:50
ORD
-
CPT
31h 30m
1 stop
R18 006Turkish Airlines
Wed, Jul 15 - Fri, Jan 15
United Airlines Logo
19:50 - 20:15
CPT
-
ORD
31h 25m
2 stops
United Airlines Logo
16:30 - 17:20
ORD
-
CPT
41h 50m
2 stops
R18 448United Airlines
Mon, Apr 27 - Mon, May 4
KLM Logo
23:15 - 18:33
JNB
-
MDW
26h 18m
2 stops
KLM Logo
13:22 - 21:20
MDW
-
JNB
24h 58m
2 stops
R21 560KLM
Wed, May 6 - Wed, May 13
KLM Logo
23:15 - 17:56
CPT
-
MDW
25h 41m
2 stops
KLM Logo
13:22 - 21:25
MDW
-
CPT
25h 03m
2 stops
R23 906KLM
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 23 March 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

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 6/5

9:45-8:35

1 stop29h 50m

Chicago O'Hare Intl

Wed 13/5

14:00-8:15

1 stop35h 15m

R14 181

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sun 3/5

9:45-8:35

1 stop29h 50m

Chicago O'Hare Intl

Wed 20/5

14:00-8:15

1 stop35h 15m

R14 385

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Wed 3/6

9:50-8:35

1 stop29h 45m

Chicago O'Hare Intl

Tue 9/6

14:00-8:20

1 stop35h 20m

R14 470
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 22/4

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Thu 30/4

10:15-14:35

1 stop21h 20m

R15 915

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 15/7

16:35-18:15

1 stop32h 40m

Chicago O'Hare Intl

Wed 19/8

11:25-11:50

1 stop41h 25m

R16 170

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 22/4

13:50-8:15

2 stops25h 25m

Chicago O'Hare Intl

Sun 3/5

10:15-14:35

1 stop21h 20m

R16 884

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 15/7

16:35-9:40

1 stop24h 05m

Chicago O'Hare Intl

Fri 15/1

20:20-11:50

1 stop31h 30m

R18 006

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 27/4

19:50-20:15

2 stops31h 25m

Chicago O'Hare Intl

Mon 4/5

16:30-17:20

2 stops41h 50m

R18 448

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Wed 6/5

23:15-18:33

2 stops26h 18m

Chicago Midway

Wed 13/5

13:22-21:20

2 stops24h 58m

R21 560

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 28/5

23:15-17:56

2 stops25h 41m

Chicago Midway

Thu 4/6

13:22-21:25

2 stops25h 03m

R23 906

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 303. 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 867.

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 R18 749 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 R16 102 on momondo.

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport
Find flights from Johannesburg OR Tambo Airport to Milwaukee
CHEAPEST MONTH TO FLY TO CHICAGO FROM JOHANNESBURG OR TAMBO AIRPORTFebruary16% cheaperFlying from Johannesburg OR Tambo Airport to Chicago costs on average just R15 303 in February
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM JOHANNESBURG OR TAMBO AIRPORTJuly15% more expensiveIt costs about R20 880 for flights to Chicago from Johannesburg OR Tambo Airport in July
MOST POPULAR MONTH TO FLY TO CHICAGO FROM JOHANNESBURG OR TAMBO AIRPORTJune390% more users visitedMore momondo users searched in flights to Chicago from Johannesburg OR Tambo Airport in June than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

R9 930

Best Round-Trip Price

R14 181

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 930 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from South Africa in the last 72 hours is R14 181 (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 R18 095.

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 384. 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 O'Hare Intl in Chicago which is the closest available airport to Grand Boulevard (30,1 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 March 2026, there are 11 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
Cape Town Intl to Chicago Flightsfrom R1 034
Johannesburg to Chicago Flightsfrom R851
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