Latest deals
Insights
When to book
FAQs
Price Alerts
Flights to Chicago Midway

R16 233 Cheap flights to Chicago Midway Airport

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 Midway Airport departing on 11/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from South Africa to Chicago Midway Airport

Cheap return flights

Enter your travel dates to find the best prices.
Virgin Atlantic Logo
21:55 - 17:29JNB-MDW
27h 34m1 stop
Virgin Atlantic Logo
10:48 - 19:00MDW-JNB
24h 12m1 stop
R18 303Virgin Atlantic
Find Deal
Tue, Jan 20 - Tue, Jan 27
Delta Logo
21:30 - 18:32JNB-MDW
29h 02m2 stops
Delta Logo
6:00 - 19:00MDW-JNB
29h 00m1 stop
R18 850Delta
Find Deal
Thu, Jan 15 - Thu, Jan 22
Delta Logo
21:55 - 16:16JNB-MDW
50h 21m2 stops
Delta Logo
19:16 - 19:00MDW-JNB
63h 44m2 stops
R18 953Delta
Find Deal
Fri, Feb 6 - Tue, Feb 10
Delta Logo
23:15 - 18:31CPT-MDW
26h 16m2 stops
Delta Logo
9:20 - 21:25MDW-CPT
29h 05m2 stops
R20 903Delta
Find Deal
Thu, May 28 - Thu, Jun 4
Delta Logo
23:59 - 18:18JNB-MDW
26h 19m2 stops
Delta Logo
11:48 - 22:05MDW-JNB
26h 17m2 stops
R20 954Delta
Find Deal
Sat, Dec 13 - Tue, Dec 30
Delta Logo
21:55 - 21:45JNB-MDW
30h 50m1 stop
Delta Logo
9:20 - 21:20MDW-JNB
29h 00m2 stops
R21 211Delta
Find Deal
Tue, Apr 14 - Wed, Apr 29
Delta Logo
23:15 - 18:31JNB-MDW
26h 16m2 stops
Delta Logo
9:30 - 21:20MDW-JNB
28h 50m2 stops
R21 365Delta
Find Deal
Tue, Apr 14 - Wed, Apr 29
Delta Logo
23:59 - 18:18JNB-MDW
26h 19m2 stops
Delta Logo
11:48 - 22:05MDW-JNB
26h 17m2 stops
R21 433Delta
Find Deal
Sat, Dec 13 - Mon, Dec 29
Delta Logo
7:55 - 17:34CPT-MDW
41h 39m2 stops
Delta Logo
6:00 - 19:15MDW-CPT
29h 15m1 stop
R21 433Delta
Find Deal
Wed, Jan 14 - Wed, Jan 21
KLM Logo
23:45 - 22:07CPT-MDW
30h 22m2 stops
KLM Logo
13:26 - 21:55MDW-CPT
24h 29m2 stops
R28 361KLM
Find Deal
Fri, Jan 16 - Fri, Jan 23

momondo Fare Finder

 
Locate flights to Chicago Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 13 550 searches and data was last updated on 2 December 2025.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Tue 20/1

21:55-17:29

1 stop27h 34m

Chicago Midway

Tue 27/1

10:48-19:00

1 stop24h 12m

R18 303

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 15/1

21:30-18:32

2 stops29h 02m

Chicago Midway

Thu 22/1

6:00-19:00

1 stop29h 00m

R18 850

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Fri 6/2

21:55-16:16

2 stops50h 21m

Chicago Midway

Tue 10/2

19:16-19:00

2 stops63h 44m

R18 953

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Thu 28/5

23:15-18:31

2 stops26h 16m

Chicago Midway

Thu 4/6

9:20-21:25

2 stops29h 05m

R20 903

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Sat 13/12

23:59-18:18

2 stops26h 19m

Chicago Midway

Tue 30/12

11:48-22:05

2 stops26h 17m

R20 954

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Tue 14/4

21:55-21:45

1 stop30h 50m

Chicago Midway

Wed 29/4

9:20-21:20

2 stops29h 00m

R21 211

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Tue 14/4

23:15-18:31

2 stops26h 16m

Chicago Midway

Wed 29/4

9:30-21:20

2 stops28h 50m

R21 365

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Sat 13/12

23:59-18:18

2 stops26h 19m

Chicago Midway

Mon 29/12

11:48-22:05

2 stops26h 17m

R21 433

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Wed 14/1

7:55-17:34

2 stops41h 39m

Chicago Midway

Wed 21/1

6:00-19:15

1 stop29h 15m

R21 433

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Fri 16/1

23:45-22:07

2 stops30h 22m

Chicago Midway

Fri 23/1

13:26-21:55

2 stops24h 29m

R28 361

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago Midway Airport from

Flights to Chicago Midway Airport – Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago Midway Airport to help you craft the best travel plan.

What is the cheapest airline that flies from South Africa to Chicago Midway?

Delta, Virgin Atlantic, and KLM are the most popular carriers operating from South Africa to Chicago Midway

Cheapest flights to Chicago Midway

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

Cheap Chicago Midway Airport flight deals and tips

Summary info about Chicago Midway Airport flight prices, duration and airlines

Best One-Way Price

R16 233

Best Round-Trip Price

R18 303

Fastest flight time

44h 22m
The best one-way flight price to Chicago from South Africa in the last 72 hours is R16 233 (Cape Town Intl to Chicago Midway).
Search Deals
The best round-trip flight price to Chicago from South Africa in the last 72 hours is R18 303 (Johannesburg OR Tambo to Chicago Midway).
Search Deals
The fastest flight to Chicago from South Africa takes 44h 22m (Johannesburg OR Tambo to Chicago Midway).
Search Deals

Frequently asked questions about flying to Chicago Midway Airport

What is the cheapest time of day to fly to Chicago Midway Airport?

Our data shows that the cheapest Chicago Midway Airport flights are usually those with Evening departure times. Evening flights are often costlier.

Is there an alternative airport near Chicago Midway Airport?

Those flying to Chicago Midway Airport could potentially find better pricing at Chicago O'Hare Intl Airport (26 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 O'Hare Intl Airport where the average price is R17 015. Users typically find the best prices when using momondo’s Airport-to-Airport Pricing Tool.

What is the absolute cheapest flight to Chicago?

The best price found on momondo to Chicago was R5 740/pp from Boston, which is 66% cheaper than the average flight price to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

When did momondo last update prices for flights to Chicago Midway Airport?

Prices for flights to Chicago Midway Airport refresh daily.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and stopovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel to Chicago Midway Airport.

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

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Travelling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Hammond

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights to Chicago. Millions of users trust and use momondo every year so you are in good company.

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?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight to Chicago.

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

Price alerts on flights to Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/1
Thu 8/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago Midway Airport MDW

Fly into one of these airports located in Chicago

Flights to Chicago O'Hare Intl Airport