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 R17 924.

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 R2 623. Users typically find the best prices when using momondo’s Airport-to-Airport Pricing Tool.

Question 9

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 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 British Airways, United Airlines, KLM and Turkish Airlines. 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 21 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 515 (from Johannesburg OR Tambo) have been found by momondo users. In 3 439 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 (7,7/10, 1 428 reviews). Most KLM flights landing in Chicago will be arriving from Minneapolis St Paul, but there are 9 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 449 (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 December 2025, there are 12 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

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 R17 503. 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 R19 499.

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 22h 45m 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 20h 47m. Keep in mind that layovers or delays could extend your travel time.

Question 20

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 R17 425. Try not to purchase tickets in the morning because they tend to be around R19 439. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 R18 051 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 385 on momondo.

Question 22

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 R16 050. 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 R16 703.

Best One-Way Price	R8 846
Best Round-Trip Price	R13 470
Fastest flight time	25h 55m
Popular in	November

R8 846 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 1/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from South Africa to Chicago

Cheap return flights

Cheap one-way flights

Cheap last-minute flights

momondo Fare Finder

Use the filters below to find and compare flights to Chicago that are best for you.

See travel insights to Chicago from

Chicago flights insights and trends

What is the cheapest month to fly to Chicago?

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

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

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

How long does it take to fly to Chicago?

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

Best Round-Trip Price

Fastest flight time

Popular in

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?

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?

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

Popular Flights to Chicago

Popular routes according to searches in the past day on momondo