R10 088 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 27/1. 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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Fly from
Route
Depart
Return
Cape TownChicago
CPT Cape Town Intl - MDW Chicago Midway
CPTMDW
Cape Town Intl
Mon 26/10
21:00-18:00
2 stops28h 00m
Chicago Midway
Sun 8/11
12:49-18:35
1 stop21h 46m
Cape TownChicago
CPT Cape Town Intl - ORD Chicago O'Hare Intl
CPTORD
Cape Town Intl
Thu 3/12
21:00-19:09
2 stops30h 09m
Chicago O'Hare Intl
Mon 11/1
9:30-18:35
1 stop25h 05m
Cape TownChicago
CPT Cape Town Intl - ORD Chicago O'Hare Intl
CPTORD
Cape Town Intl
Sun 25/10
13:50-8:40
2 stops25h 50m
Chicago O'Hare Intl
Thu 29/10
10:15-14:10
1 stop20h 55m
JohannesburgChicago
JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl
JNBORD
Johannesburg OR Tambo
Wed 28/10
0:20-19:20
1 stop26h 00m
Chicago O'Hare Intl
Wed 25/11
20:15-22:25
1 stop42h 10m
JohannesburgChicago
JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl
JNBORD
Johannesburg OR Tambo
Fri 23/10
14:30-8:15
2 stops24h 45m
Chicago O'Hare Intl
Sat 31/10
10:15-13:30
1 stop20h 15m
JohannesburgChicago
JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl
JNBORD
Johannesburg OR Tambo
Sun 25/10
18:50-11:00
1 stop23h 10m
Chicago O'Hare Intl
Thu 29/10
12:45-22:25
1 stop26h 40m
JohannesburgChicago
JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl
JNBORD
Johannesburg OR Tambo
Tue 24/11
22:00-10:48
1 stop20h 48m
Chicago O'Hare Intl
Thu 3/12
12:55-18:35
1 stop21h 40m
JohannesburgChicago
JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl
JNBORD
Johannesburg OR Tambo
Thu 26/11
22:00-13:09
1 stop23h 09m
Chicago O'Hare Intl
Thu 3/12
15:35-18:35
1 stop19h 00m
Cape TownChicago
CPT Cape Town Intl - ORD Chicago O'Hare Intl
CPTORD
Cape Town Intl
Mon 2/11
15:20-16:15
2 stops32h 55m
Chicago O'Hare Intl
Mon 9/11
18:25-6:25
1 stop28h 00m
JohannesburgChicago
JNB Johannesburg OR Tambo - ORD Chicago O'Hare Intl
JNBORD
Johannesburg OR Tambo
Tue 27/10
23:59-15:25
1 stop22h 26m
Chicago O'Hare Intl
Wed 25/11
16:25-22:00
1 stop21h 35m
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 November is, on average, the cheapest month to fly to Chicago from South Africa, with most prices found around R16 714. If you are unable to visit Chicago during the month of November, then departing from South Africa during the month February is also very affordable. Most momondo users find prices during this month for around R16 747.
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 700 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 399 on momondo.
Cheap Chicago flight deals and tips
Summary info about Chicago flight prices, duration and airlines
Best One-Way Price | R10 104 |
|---|---|
Best Round-Trip Price | R15 124 |
Fastest flight time | 26h 55m |
Popular in | January |
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 68 days out, which is when prices tend to be around R18 670.
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 R4 775. Users typically find the best prices when using momondo’s Airport-to-Airport Pricing Tool.
Are there flights to Near North Side?
Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Near North Side (15,5 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 October 2026, there are 8 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 locationsWhy 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.