R2 308+ Cheap flights from Chicago
This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 14/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
What to know about flights from Chicago
Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 26 June 2025.
Cheapest airline | United Airlines |
|---|---|
Good round-trip deal | R5 363 or less |
Good one-way deal | R1 571 or less |
Find flights from Chicago
Cheapest flights from ChicagoExplore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 26 June 2025.
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 26 June 2025.
Find flights from Chicago within your budget
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 26 June 2025. In the last 7 days, Cheapflights users made a total of 594 507 searches
Fly to
Route
Depart
Return
Price
ChicagoCape Town
ORD - CPT
ORDCPT
Chicago O'Hare Intl
Wed 8/10
10:15-14:35
1 stop21h 20m
Cape Town Intl
Wed 22/10
14:35-8:15
2 stops24h 40m
ChicagoCape Town
ORD - CPT
ORDCPT
Chicago O'Hare Intl
Wed 12/11
11:50-11:50
1 stop40h 00m
Cape Town Intl
Tue 25/11
17:15-10:05
1 stop24h 50m
ChicagoCape Town
ORD - CPT
ORDCPT
Chicago O'Hare Intl
Mon 18/8
10:05-11:00
2 stops41h 55m
Cape Town Intl
Wed 3/9
18:55-13:55
1 stop26h 00m
ChicagoCape Town
ORD - CPT
ORDCPT
Chicago O'Hare Intl
Tue 11/11
21:45-10:20
1 stop28h 35m
Cape Town Intl
Mon 17/11
22:00-13:55
1 stop23h 55m
ChicagoJohannesburg
ORD - JNB
ORDJNB
Chicago O'Hare Intl
Fri 14/11
21:45-7:30
1 stop25h 45m
Johannesburg OR Tambo
Thu 8/1
19:45-13:55
1 stop26h 10m
ChicagoJohannesburg
ORD - JNB
ORDJNB
Chicago O'Hare Intl
Wed 17/9
7:30-0:25
2 stops33h 55m
Johannesburg OR Tambo
Wed 1/10
1:25-17:36
2 stops47h 11m
ChicagoCape Town
ORD - CPT
ORDCPT
Chicago O'Hare Intl
Sat 20/9
23:45-14:35
2 stops31h 50m
Cape Town Intl
Fri 26/9
16:35-9:40
1 stop24h 05m
ChicagoJohannesburg
ORD - JNB
ORDJNB
Chicago O'Hare Intl
Sat 6/12
9:45-20:10
1 stop26h 25m
Johannesburg OR Tambo
Tue 6/1
8:20-7:40
2 stops31h 20m
ChicagoJohannesburg
ORD - JNB
ORDJNB
Chicago O'Hare Intl
Thu 18/9
6:20-9:35
2 stops44h 15m
Johannesburg OR Tambo
Sat 4/10
16:50-15:05
2 stops53h 15m
ChicagoJohannesburg
ORD - JNB
ORDJNB
Chicago O'Hare Intl
Tue 19/8
7:00-15:50
2 stops25h 50m
Johannesburg OR Tambo
Thu 18/9
1:25-12:38
2 stops42h 13m
Best time to book a flight from Chicago
Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
Travel insights for flights from Chicago
Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.
When is the best time to book a flight from Chicago?
Use this chart to determine the optimal time to book a return flight from Chicago to OR Tambo. Price data was last updated on 20 June 2025.
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago?
Currently, November is the cheapest month in which you can book a flight from Chicago (average of R14 378). Flying from Chicago in July will prove the most costly (average of R22 899). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
Which airlines fly from Chicago?
When flying from Chicago check dates and pricing for the following: United Airlines. As it departs for the following popular destinations: Johannesburg.
What are popular destinations to fly to from Chicago?
From Chicago you can expect to find greater availability for the following destinations: New York (1 239 flights per day), Detroit (1 052 flights per day) and Los Angeles (645 flights per day).
What is the cheapest place to fly to from Chicago?
The cheapest city to fly to from Chicago is New York, with prices starting at R1 571. Explore other affordable destinations below.
Airline reviews for flights from Chicago
Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 594 507 searches.
See what other customers who have flown with Emirates, Delta, andKLM from Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Muhammed,Jun 2025
DXB - DUR
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Muhammed,Jun 2025
DXB - DUR
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Muhammed,Jun 2025
DXB - DUR
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Muhammed,Jun 2025
DXB - DUR
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Muhammed,Jun 2025
DXB - DUR
Boarding
Comfort
Crew
Overall
Food
Entertainment
Reviews
Muhammed,Jun 2025
DXB - DUR
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Related info for your journey
Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 26 June 2025.
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How does Cheapflights help users find flights from Chicago?
Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Chicago?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.
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Certainly. Search results for flights from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
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