Latest deals
Insights
When to book
FAQs
Price Alerts
Flights to Chicago

R8 525 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 9/3. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from South Africa to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Ethiopian Air Logo
14:30 - 8:40
JNB
-
ORD
25h 10m
2 stops
Ethiopian Air Logo
10:15 - 20:10
ORD
-
JNB
26h 55m
1 stop
R13 333Ethiopian Air
Wed, Mar 25 - Wed, Apr 1
Turkish Airlines Logo
19:10 - 19:25
JNB
-
ORD
31h 15m
1 stop
Turkish Airlines Logo
20:10 - 10:30
ORD
-
JNB
31h 20m
1 stop
R13 813Turkish Airlines
Thu, Mar 19 - Wed, Apr 1
Turkish Airlines Logo
19:10 - 11:05
JNB
-
ORD
22h 55m
1 stop
Turkish Airlines Logo
20:10 - 10:30
ORD
-
JNB
31h 20m
1 stop
R13 909Turkish Airlines
Thu, Mar 19 - Wed, Apr 1
United Airlines Logo
20:50 - 11:51
CPT
-
ORD
23h 01m
2 stops
United Airlines Logo
16:30 - 12:40
ORD
-
CPT
37h 10m
2 stops
R16 105United Airlines
Thu, Mar 5 - Thu, Mar 12
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
17:10 - 10:40
ORD
-
DUR
33h 30m
2 stops
R17 275British Airways
Thu, Feb 19 - Mon, Feb 23
British Airways Logo
11:15 - 13:50
DUR
-
ORD
34h 35m
2 stops
British Airways Logo
17:10 - 10:40
ORD
-
DUR
33h 30m
2 stops
R17 467British Airways
Thu, Feb 19 - Mon, Feb 23
KLM Logo
23:59 - 18:40
JNB
-
MDW
25h 41m
2 stops
KLM Logo
13:10 - 21:20
MDW
-
JNB
25h 10m
2 stops
R22 931KLM
Thu, Mar 19 - Wed, Apr 1
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m
1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m
1 stop
R23 685Emirates
Thu, Feb 19 - Mon, Feb 23
Emirates Logo
19:10 - 14:55
DUR
-
ORD
27h 45m
1 stop
Emirates Logo
19:45 - 17:10
ORD
-
DUR
37h 25m
1 stop
R23 957Emirates
Thu, Feb 19 - Mon, Feb 23
KLM Logo
23:59 - 18:40
JNB
-
MDW
26h 41m
2 stops
KLM Logo
13:10 - 22:05
MDW
-
JNB
25h 55m
2 stops
R27 130KLM
Sat, Feb 21 - Mon, Mar 9

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 9 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

Wed 25/3

14:30-8:40

2 stops25h 10m

Chicago O'Hare Intl

Wed 1/4

10:15-20:10

1 stop26h 55m

R13 333

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 19/3

19:10-19:25

1 stop31h 15m

Chicago O'Hare Intl

Wed 1/4

20:10-10:30

1 stop31h 20m

R13 813

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Thu 19/3

19:10-11:05

1 stop22h 55m

Chicago O'Hare Intl

Wed 1/4

20:10-10:30

1 stop31h 20m

R13 909

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 5/3

20:50-11:51

2 stops23h 01m

Chicago O'Hare Intl

Thu 12/3

16:30-12:40

2 stops37h 10m

R16 105

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Thu 19/2

11:15-13:50

2 stops34h 35m

Chicago O'Hare Intl

Mon 23/2

17:10-10:40

2 stops33h 30m

R17 275

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Thu 19/2

11:15-13:50

2 stops34h 35m

Chicago O'Hare Intl

Mon 23/2

17:10-10:40

2 stops33h 30m

R17 467

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 19/3

23:59-18:40

2 stops25h 41m

Chicago Midway

Wed 1/4

13:10-21:20

2 stops25h 10m

R22 931

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Thu 19/2

19:10-14:55

1 stop27h 45m

Chicago O'Hare Intl

Mon 23/2

19:45-17:10

1 stop37h 25m

R23 685

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Thu 19/2

19:10-14:55

1 stop27h 45m

Chicago O'Hare Intl

Mon 23/2

19:45-17:10

1 stop37h 25m

R23 957

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Sat 21/2

23:59-18:40

2 stops26h 41m

Chicago Midway

Mon 9/3

13:10-22:05

2 stops25h 55m

R27 130

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 015. 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 897.

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 659 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 159 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

R8 525

Best Round-Trip Price

R13 333

Fastest flight time

21h 32m

Popular in

November
The best one-way flight price to Chicago from South Africa in the last 72 hours is R8 525 (Durban King Shaka 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 333 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 21h 32m (Cape Town Intl to Chicago Midway).
Search Deals
November has the highest demand for flights to Chicago, with a 9% 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 69 days out, which is when prices tend to be around R17 284.

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 418. 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 11/3
Wed 18/3
By creating a price alert you accept our terms of use and privacy policy.

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 R881
Johannesburg to Chicago Flightsfrom R832
Durban King Shaka Intl to Chicago Flightsfrom R1 098