Which airlines fly to Chicago?

For flights from South Africa to Chicago, most momondo users will book with popular airlines such as British Airways, KLM, United Airlines and Turkish Airlines. Depending on what airport you fly from, you may have other airlines to choose from.

Emirates Flights to Chicago

Emirates is a popular choice for users travelling to Chicago. It operates 14 flights every week to Chicago, most often flying from Cancun. Emirates ticket prices will depend on when and where you need to fly from - deals as low as R18 671 (from Durban King Shaka Intl) have been found by momondo users. In 3 334 reviews, momondo users have rated Emirates at an average score of 8,1/10.

KLM Flights to Chicago

Another popular choice for flights to Chicago is KLM (7,8/10, 1 385 reviews). Most KLM flights landing in Chicago will be arriving from Minneapolis St Paul, but there are 28 KLM flights to Chicago from all departure points globally so prices can vary significantly. The best KLM deal found on momondo this week was R17 046 (Cape Town Intl to Chicago, return).

How long does it take to fly to Chicago?

Flight times from South Africa to Chicago vary, but if you’re flying out of Johannesburg OR Tambo and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 22h 21m on average. Another popular route from South Africa to Chicago is flying from Cape Town Intl to Chicago O'Hare Intl, which will take roughly 25h 05m. Keep in mind that layovers or delays could extend your travel time.

R9 671 Cheap Flights to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

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

Trusted and free

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

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from South Africa to Chicago

Round-trip

One-way

Cheap return flights

9:50 - 8:55JNB-ORD

30h 05m1 stop

14:00 - 8:20ORD-JNB

35h 20m1 stop

R14 949Etihad Airways

Find Deal

Mon, Mar 9 - Thu, Jul 9

13:50 - 7:40CPT-ORD

25h 50m2 stops

9:45 - 14:35ORD-CPT

20h 50m1 stop

R14 949Ethiopian Air

Find Deal

Tue, Nov 18 - Mon, Nov 24

20:50 - 9:48CPT-ORD

20h 58m1 stop

14:39 - 16:10ORD-CPT

17h 31m1 stop

R16 251United Airlines

Find Deal

Mon, Nov 17 - Mon, Nov 24

17:15 - 10:05CPT-ORD

24h 50m1 stop

20:20 - 11:50ORD-CPT

31h 30m1 stop

R16 737Turkish Airlines

Find Deal

Thu, Nov 20 - Thu, Nov 27

21:20 - 20:15JNB-ORD

29h 55m2 stops

6:00 - 17:45ORD-JNB

28h 45m2 stops

R17 206United Airlines

Find Deal

Sat, Sep 27 - Sat, Oct 4

17:15 - 10:05CPT-ORD

24h 50m1 stop

20:20 - 11:50ORD-CPT

31h 30m1 stop

R17 779Turkish Airlines

Find Deal

Thu, Nov 20 - Tue, Nov 25

20:35 - 19:50CPT-ORD

30h 15m2 stops

21:45 - 12:40ORD-CPT

31h 55m2 stops

R18 925British Airways

Find Deal

Wed, Mar 11 - Sun, Mar 15

22:10 - 13:50CPT-ORD

23h 40m1 stop

18:30 - 12:10ORD-CPT

33h 40m2 stops

R19 359British Airways

Find Deal

Sat, Nov 22 - Sun, Nov 30

23:59 - 14:20JNB-ORD

22h 21m1 stop

16:25 - 22:05ORD-JNB

21h 40m1 stop

R19 480KLM

Find Deal

Sat, Dec 13 - Sat, Jan 10

23:59 - 14:20JNB-ORD

22h 21m1 stop

16:25 - 22:05ORD-JNB

21h 40m1 stop

R19 775KLM

Find Deal

Fri, Dec 12 - Sat, Jan 10

Fly from

Route

Depart

Return

Price

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Mon 9/3

9:50-8:55

1 stop30h 05m

Chicago O'Hare Intl

Thu 9/7

14:00-8:20

1 stop35h 20m

R14 949

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Tue 18/11

13:50-7:40

2 stops25h 50m

Chicago O'Hare Intl

Mon 24/11

9:45-14:35

1 stop20h 50m

R14 949

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Mon 17/11

20:50-9:48

1 stop20h 58m

Chicago O'Hare Intl

Mon 24/11

14:39-16:10

1 stop17h 31m

R16 251

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 20/11

17:15-10:05

1 stop24h 50m

Chicago O'Hare Intl

Thu 27/11

20:20-11:50

1 stop31h 30m

R16 737

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sat 27/9

21:20-20:15

2 stops29h 55m

Chicago O'Hare Intl

Sat 4/10

6:00-17:45

2 stops28h 45m

R17 206

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Thu 20/11

17:15-10:05

1 stop24h 50m

Chicago O'Hare Intl

Tue 25/11

20:20-11:50

1 stop31h 30m

R17 779

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Wed 11/3

20:35-19:50

2 stops30h 15m

Chicago O'Hare Intl

Sun 15/3

21:45-12:40

2 stops31h 55m

R18 925

Cape TownChicago

CPT - ORD

CPTORD

Cape Town Intl

Sat 22/11

22:10-13:50

1 stop23h 40m

Chicago O'Hare Intl

Sun 30/11

18:30-12:10

2 stops33h 40m

R19 359

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Sat 13/12

23:59-14:20

1 stop22h 21m

Chicago O'Hare Intl

Sat 10/1

16:25-22:05

1 stop21h 40m

R19 480

JohannesburgChicago

JNB - ORD

JNBORD

Johannesburg OR Tambo

Fri 12/12

23:59-14:20

1 stop22h 21m

Chicago O'Hare Intl

Sat 10/1

16:25-22:05

1 stop21h 40m

R19 775

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

Prices

Other information

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 R16 858. 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 R17 310.

What is the cheapest day to depart on your flight to Chicago?

On average, the least expensive day to fly to Chicago from South Africa is on a Thursday. momondo users have found tickets for Thursday departures for as low as R18 138. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Saturday is R20 207.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest South Africa to Chicago flights are usually those with departure times in the afternoon. Our users have found flights to Chicago in the afternoon for as low as R18 057. Try not to purchase tickets in the morning because they tend to be around R20 145. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 479 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 R17 015 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

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price	R9 671
Best Round-Trip Price	R14 949
Fastest flight time	22h 55m
Popular in	December

The best one-way flight price to Chicago from South Africa in the last 72 hours is R9 671 (Cape Town 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 R14 949 (Johannesburg OR Tambo to Chicago O'Hare Intl).

Search Deals

The fastest flight to Chicago from South Africa takes 22h 55m (Johannesburg OR Tambo to Chicago O'Hare Intl).

Search Deals

December has the highest demand for flights to Chicago, with a 1% 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 R18 712.

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

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from San Diego found flights 14% cheaper than the average price of flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Lake View?

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Lake View (18,8 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 September 2025, 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.

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.