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Flights to Chicago Midway

R16 164 Cheap flights to Chicago Midway Airport

This is the cheapest return flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago Midway Airport departing on 19/7. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from South Africa to Chicago Midway Airport

Cheap return flights

Enter your travel dates to find the best prices.
Delta Logo
20:05 - 10:05
CPT
-
MDW
21h 00m
1 stop
Delta Logo
18:58 - 17:50
MDW
-
CPT
63h 52m
2 stops
R16 164Delta
Sun, Jul 19 - Tue, Jul 28
Delta Logo
20:05 - 12:39
CPT
-
MDW
23h 34m
2 stops
Delta Logo
12:46 - 17:50
MDW
-
CPT
22h 04m
1 stop
R16 344Delta
Sun, Aug 2 - Thu, Aug 13
KLM Logo
23:15 - 18:19
CPT
-
MDW
26h 04m
2 stops
KLM Logo
13:19 - 21:25
MDW
-
CPT
25h 06m
2 stops
R16 427KLM
Tue, Sep 8 - Sat, Sep 26
Virgin Atlantic Logo
21:40 - 22:10
JNB
-
MDW
32h 30m
2 stops
Virgin Atlantic Logo
13:05 - 8:20
MDW
-
JNB
35h 15m
2 stops
R17 199Virgin Atlantic
Tue, Dec 1 - Mon, Mar 1
Delta Logo
23:15 - 18:25
CPT
-
MDW
50h 10m
2 stops
Delta Logo
6:00 - 17:50
MDW
-
CPT
28h 50m
1 stop
R17 215Delta
Sat, Jul 18 - Thu, Jul 30
Delta Logo
20:05 - 10:05
CPT
-
MDW
21h 00m
1 stop
Delta Logo
9:54 - 17:50
MDW
-
CPT
24h 56m
2 stops
R17 412Delta
Sun, Jul 19 - Thu, Jul 30
Multiple Airlines Logo
20:05 - 22:15
CPT
-
MDW
33h 10m
1 stop
Multiple Airlines Logo
11:05 - 23:35
MDW
-
CPT
29h 30m
2 stops
R17 494Multiple Airlines
Sun, Jul 19 - Tue, Jul 28
KLM Logo
23:15 - 18:25
CPT
-
MDW
50h 10m
2 stops
KLM Logo
6:00 - 21:25
MDW
-
CPT
32h 25m
2 stops
R17 938KLM
Sun, Jul 19 - Tue, Jul 28
Virgin Atlantic Logo
21:40 - 16:25
JNB
-
MDW
26h 45m
2 stops
Virgin Atlantic Logo
13:05 - 8:20
MDW
-
JNB
35h 15m
2 stops
R19 696Virgin Atlantic
Tue, Nov 24 - Thu, Jan 21
Multiple Airlines Logo
20:15 - 22:36
JNB
-
MDW
33h 21m
2 stops
Multiple Airlines Logo
13:00 - 22:25
MDW
-
JNB
26h 25m
2 stops
R21 749Multiple Airlines
Thu, Sep 3 - Thu, Sep 17

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 27 June 2026.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 19/7

20:05-10:05

1 stop21h 00m

Chicago Midway

Tue 28/7

18:58-17:50

2 stops63h 52m

R16 164
Fastest return journey

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 2/8

20:05-12:39

2 stops23h 34m

Chicago Midway

Thu 13/8

12:46-17:50

1 stop22h 04m

R16 344

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Tue 8/9

23:15-18:19

2 stops26h 04m

Chicago Midway

Sat 26/9

13:19-21:25

2 stops25h 06m

R16 427

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Tue 1/12

21:40-22:10

2 stops32h 30m

Chicago Midway

Mon 1/3

13:05-8:20

2 stops35h 15m

R17 199

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sat 18/7

23:15-18:25

2 stops50h 10m

Chicago Midway

Thu 30/7

6:00-17:50

1 stop28h 50m

R17 215

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 19/7

20:05-10:05

1 stop21h 00m

Chicago Midway

Thu 30/7

9:54-17:50

2 stops24h 56m

R17 412

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 19/7

20:05-22:15

1 stop33h 10m

Chicago Midway

Tue 28/7

11:05-23:35

2 stops29h 30m

R17 494

Cape TownChicago

CPT - MDW

CPTMDW

Cape Town Intl

Sun 19/7

23:15-18:25

2 stops50h 10m

Chicago Midway

Tue 28/7

6:00-21:25

2 stops32h 25m

R17 938

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Tue 24/11

21:40-16:25

2 stops26h 45m

Chicago Midway

Thu 21/1

13:05-8:20

2 stops35h 15m

R19 696

JohannesburgChicago

JNB - MDW

JNBMDW

Johannesburg OR Tambo

Thu 3/9

20:15-22:36

2 stops33h 21m

Chicago Midway

Thu 17/9

13:00-22:25

2 stops26h 25m

R21 749

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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

R19 301

Best Round-Trip Price

R16 164

Fastest flight time

44h 22m
The best one-way flight price to Chicago from South Africa in the last 5 days is R19 301 (Johannesburg OR Tambo to Chicago Midway).
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The best round-trip flight price to Chicago from South Africa in the last 5 days is R16 164 (Cape Town Intl to Chicago Midway).
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The fastest flight to Chicago from South Africa takes 44h 22m (Johannesburg OR Tambo to Chicago Midway).
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Frequently asked questions about flying to Chicago Midway Airport

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 R14 220. Users typically find the best prices when using 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

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Find better results for your trip to Chicago Midway Airport MDW

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