Question 1

Why should I use momondo to find a flight deal to Chicago?

Accepted Answer

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.

Question 2

Can I find flights to Chicago with flexible booking policies on momondo?

Accepted Answer

Yes. momondo allows you to filter the results for flights to Chicago to just show those with flexible booking policies.

Question 3

How can momondo help me find flights to Chicago?

Accepted Answer

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.

Question 4

I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?

Accepted Answer

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.

Question 5

When is it best to fly to Chicago to go sightseeing?

Accepted Answer

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.

Question 6

How far in advance should I book a flight to Chicago?

Accepted Answer

The best time to book a flight to Chicago from South Africa is 61 days out, which is when prices tend to be around R18 165.

Question 7

Is there an alternative airport near Chicago?

Accepted Answer

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.

Question 8

Is there a cheaper alternative to flying into Chicago?

Accepted Answer

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

Question 9

Are there flights to Near North Side?

Accepted Answer

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Near North Side (15,5 km away).

Question 10

What’s the closest airport to McCormick Place?

Accepted Answer

The closest airport to McCormick Place is 12,7 km away - Chicago’s Chicago Midway airport.

Question 11

Which airlines fly to Chicago?

Accepted Answer

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

Question 12

Emirates Flights to Chicago

Accepted Answer

Emirates is a popular choice for users travelling to Chicago. It operates 72 flights every week to Chicago, most often flying from Houston George Bush Intcntl. Emirates ticket prices will depend on when and where you need to fly from - deals as low as R20 165 (from Johannesburg OR Tambo) have been found by momondo users. In 3 659 reviews, momondo users have rated Emirates at an average score of 8,1/10.

Question 13

KLM Flights to Chicago

Accepted Answer

Another popular choice for flights to Chicago is KLM (7,8/10, 1 580 reviews). Most KLM flights landing in Chicago will be arriving from Minneapolis St Paul, but there are 20 KLM flights to Chicago from all departure points globally so prices can vary significantly. The best KLM deal found on momondo this week was R16 393 (Cape Town Intl to Chicago, return).

Question 14

When did momondo last update prices for flights to Chicago?

Accepted Answer

Prices for flights to Chicago were last updated today.

Question 15

How many operators does momondo search for flights to Chicago?

Accepted Answer

As of September 2026, there are 9 operators available to choose from for flights to Chicago.

Question 16

How old do you have to be to fly to Chicago?

Accepted Answer

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.

Question 17

What documentation or ID do you need to fly to Chicago?

Accepted Answer

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.

Question 18

How far in advance should I book a flight to Chicago?

Accepted Answer

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 348 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 953 on momondo.

Question 19

How long does it take to fly to Chicago?

Accepted Answer

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 23h 10m 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 23h 04m. Keep in mind that layovers or delays could extend your travel time.

Question 20

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of November is, on average, the cheapest month to fly to Chicago from South Africa, with most prices found around R15 823. 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 R15 904.

Best One-Way Price	R9 899
Best Round-Trip Price	R15 222
Fastest flight time	25h 55m
Popular in	January

R9 899 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 5/11. 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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