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 69 days out, which is when prices tend to be around R19 152.

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

Question 9

What is the absolute cheapest flight to Chicago?

Accepted Answer

Users booking trips to Chicago from San Diego found flights 13% 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.

Question 10

Are there flights to Edgewater?

Accepted Answer

Yes, if you fly to Chicago O'Hare Intl in Chicago which is the closest available airport to Edgewater (20,1 km away).

Question 11

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 12

Which airlines fly to Chicago?

Accepted Answer

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

Question 13

Emirates Flights to Chicago

Accepted Answer

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 979 (from Durban King Shaka Intl) have been found by momondo users. In 3 317 reviews, momondo users have rated Emirates at an average score of 8,1/10.

Question 14

KLM Flights to Chicago

Accepted Answer

Another popular choice for flights to Chicago is KLM (7,8/10, 1 388 reviews). Most KLM flights landing in Chicago will be arriving from Minneapolis St Paul, but there are 27 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 328 (Cape Town Intl to Chicago, return).

Question 15

When did momondo last update prices for flights to Chicago?

Accepted Answer

Prices for flights to Chicago were last updated today.

Question 16

How many operators does momondo search for flights to Chicago?

Accepted Answer

As of August 2025, there are 11 operators available to choose from for flights to Chicago.

Question 17

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 18

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 19

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

Accepted Answer

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 438. 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 540.

Question 20

What is the cheapest month to fly to Chicago?

Accepted Answer

The month of February is, on average, the cheapest month to fly to Chicago from South Africa, with most prices found around R17 172. 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 R17 772.

Question 21

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 R20 131 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 737 on momondo.

Question 22

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

Accepted Answer

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 356. Try not to purchase tickets in the morning because they tend to be around R20 477. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 23

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 22h 53m 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 24h 40m. Keep in mind that layovers or delays could extend your travel time.

CHEAPEST MONTH TO FLY TO CHICAGO FROM JOHANNESBURG OR TAMBO AIRPORT	February	11% cheaper	Flying from Johannesburg OR Tambo Airport to Chicago costs on average just R17 172 in February
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM JOHANNESBURG OR TAMBO AIRPORT	December	12% more expensive	It costs about R21 531 for flights to Chicago from Johannesburg OR Tambo Airport in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM JOHANNESBURG OR TAMBO AIRPORT	June	497% more users visited	More momondo users searched in flights to Chicago from Johannesburg OR Tambo Airport in June than any other month

Best One-Way Price	R10 219
Best Round-Trip Price	R14 807
Fastest flight time	24h 05m
Popular in	March

R10 219 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 21/9. 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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Frequently asked questions about flying to Chicago

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

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

Is there an alternative airport near Chicago?

Is there a cheaper alternative to flying into Chicago?

What is the absolute cheapest flight to Chicago?

Are there flights to Edgewater?

What’s the closest airport to McCormick Place?

When did momondo last update prices for flights to Chicago?

How many operators does momondo search for flights to Chicago?

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

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

Travelling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights to Chicago?

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

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