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

R10 734 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 1/12. 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

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.
Turkish Airlines Logo
18:50 - 19:20
JNB
-
ORD
31h 30m
1 stop
Turkish Airlines Logo
20:15 - 11:00
ORD
-
JNB
30h 45m
1 stop
R15 348Turkish Airlines
Thu, Oct 29 - Thu, Nov 12
Turkish Airlines Logo
18:50 - 19:20
JNB
-
ORD
31h 30m
1 stop
Turkish Airlines Logo
20:15 - 11:00
ORD
-
JNB
30h 45m
1 stop
R15 575Turkish Airlines
Tue, Oct 27 - Wed, Nov 25
KLM Logo
23:15 - 14:30
CPT
-
ORD
22h 15m
1 stop
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 320KLM
Tue, Jul 28 - Sat, Aug 15
United Airlines Logo
22:00 - 22:06
JNB
-
ORD
31h 06m
1 stop
United Airlines Logo
14:31 - 18:30
ORD
-
JNB
20h 59m
1 stop
R16 401United Airlines
Tue, Jul 21 - Tue, Aug 25
Etihad Airways Logo
9:45 - 15:40
JNB
-
ORD
36h 55m
1 stop
Etihad Airways Logo
14:00 - 8:20
ORD
-
JNB
35h 20m
1 stop
R16 465Etihad Airways
Mon, Jul 6 - Mon, Aug 10
United Airlines Logo
20:00 - 11:48
CPT
-
ORD
22h 48m
1 stop
United Airlines Logo
11:03 - 15:20
ORD
-
CPT
21h 17m
1 stop
R16 482United Airlines
Tue, Jul 14 - Sat, Aug 1
Etihad Airways Logo
9:45 - 8:35
JNB
-
ORD
29h 50m
1 stop
Etihad Airways Logo
13:10 - 8:20
ORD
-
JNB
35h 10m
1 stop
R16 579Etihad Airways
Mon, Sep 7 - Wed, Mar 3
KLM Logo
23:15 - 20:31
CPT
-
ORD
28h 16m
2 stops
KLM Logo
16:20 - 21:25
ORD
-
CPT
22h 05m
1 stop
R16 886KLM
Fri, Jul 10 - Sat, Jul 25
British Airways Logo
11:15 - 12:30
DUR
-
ORD
32h 15m
2 stops
British Airways Logo
22:30 - 10:40
ORD
-
DUR
29h 10m
2 stops
R18 635British Airways
Tue, Jul 21 - Tue, Aug 18
British Airways Logo
11:15 - 18:45
DUR
-
ORD
39h 30m
2 stops
British Airways Logo
21:45 - 10:40
ORD
-
DUR
52h 55m
2 stops
R20 853British Airways
Sun, Nov 22 - Thu, Nov 26

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 17 June 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

Thu 29/10

18:50-19:20

1 stop31h 30m

Chicago O'Hare Intl

Thu 12/11

20:15-11:00

1 stop30h 45m

R15 348

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 27/10

18:50-19:20

1 stop31h 30m

Chicago O'Hare Intl

Wed 25/11

20:15-11:00

1 stop30h 45m

R15 575

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 28/7

23:15-14:30

1 stop22h 15m

Chicago O'Hare Intl

Sat 15/8

16:20-21:25

1 stop22h 05m

R16 320

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Tue 21/7

22:00-22:06

1 stop31h 06m

Chicago O'Hare Intl

Tue 25/8

14:31-18:30

1 stop20h 59m

R16 401

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 6/7

9:45-15:40

1 stop36h 55m

Chicago O'Hare Intl

Mon 10/8

14:00-8:20

1 stop35h 20m

R16 465
Fastest return journey

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 14/7

20:00-11:48

1 stop22h 48m

Chicago O'Hare Intl

Sat 1/8

11:03-15:20

1 stop21h 17m

R16 482

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 7/9

9:45-8:35

1 stop29h 50m

Chicago O'Hare Intl

Wed 3/3

13:10-8:20

1 stop35h 10m

R16 579

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Fri 10/7

23:15-20:31

2 stops28h 16m

Chicago O'Hare Intl

Sat 25/7

16:20-21:25

1 stop22h 05m

R16 886

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Tue 21/7

11:15-12:30

2 stops32h 15m

Chicago O'Hare Intl

Tue 18/8

22:30-10:40

2 stops29h 10m

R18 635

DurbanChicago

DUR - ORD

DURORD

Durban King Shaka Intl

Sun 22/11

11:15-18:45

2 stops39h 30m

Chicago O'Hare Intl

Thu 26/11

21:45-10:40

2 stops52h 55m

R20 853

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 R14 830. 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 445.

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 563 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 089 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

R10 734

Best Round-Trip Price

R15 348

Fastest flight time

24h 40m

Popular in

January
The best one-way flight price to Chicago from South Africa in the last 5 days is R10 734 (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from South Africa in the last 5 days is R15 348 (Johannesburg OR Tambo to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from South Africa takes 24h 40m (Cape Town Intl to Chicago O'Hare Intl).
Search Deals
January has the highest demand for flights to Chicago, with a 8% 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 742.

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 135. Users typically find the best prices when using momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Kenwood?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Kenwood (12,9 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 June 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.

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
Fri 17/7
Fri 24/7
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
Johannesburg to Chicago Flightsfrom R962
Cape Town Intl to Chicago Flightsfrom R994
Durban King Shaka Intl to Chicago Flightsfrom R1 464