MDW

R15 134 Find Cheap Flights to Chicago Midway Airport – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 29% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest return flight
R15 134
Typical prices: R16 764-R25 138
Virgin Atlantic
Tue 6/11Thu 22/11
CPT - MDW • 2 stops
Cheapest one-way flight
R15 449
Typical prices: R15 211-R19 743
Virgin Atlantic
Tue 25/12
CPT - MDW • 1 stop
Top airlines
Virgin Atlantic
Best reviews • 7,5 score
Airline reviews
Airline reviews
Top routes
CPT - CHI
Cheapest • 1% average savings
JNB - CHI
Most popular
Insights
Insights
When to travel
September
Cheapest • 11% price drop
June
Most popular
Good to know
+1
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights to Midway

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Midway

Fri, Nov 6 - Sun, Nov 22
Virgin Atlantic Logo
21:00 - 22:33Cape Town  Cape Town Intl-Chicago Chicago Midway
33h 33m2 stops London Heathrow Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
11:27 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
23h 08m1 stop Atlanta Hartsfield-Jackson
R15 134Virgin Atlantic
3+ days ago
Fri, Nov 6 - Sun, Nov 22
Delta Logo
20:50 - 11:47Cape Town  Cape Town Intl-Chicago Chicago Midway
22h 57m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
Delta Logo
9:30 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
25h 05m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
R15 880Delta
3+ days ago
Fri, Nov 6 - Sun, Nov 22
Delta Logo
20:50 - 10:37Cape Town  Cape Town Intl-Chicago Chicago Midway
21h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
17:13 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
17h 22m1 stop Atlanta Hartsfield-Jackson
R15 880Delta
3+ days ago
Mon, Feb 1 - Fri, Feb 12
Virgin Atlantic Logo
20:10 - 22:10Johannesburg  Johannesburg OR Tambo-Chicago Chicago Midway
34h 00m2 stops London Heathrow Atlanta Hartsfield-Jackson
Virgin Atlantic Logo
10:35 - 19:10Chicago  Chicago Midway-Johannesburg Johannesburg OR Tambo
24h 35m1 stop Atlanta Hartsfield-Jackson
R16 991Virgin Atlantic
3+ days ago
Fri, Dec 25 - Wed, Jan 13
Delta Logo
0:30 - 8:50Cape Town  Cape Town Intl-Chicago Chicago Midway
40h 20m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
Delta Logo
6:00 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
28h 35m1 stop Atlanta Hartsfield-Jackson
R18 085Delta
3+ days ago
Fri, Dec 25 - Mon, Jan 11
Delta Logo
0:30 - 8:50Cape Town  Cape Town Intl-Chicago Chicago Midway
40h 20m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
Delta Logo
6:00 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
28h 35m1 stop Atlanta Hartsfield-Jackson
R18 085Delta
3+ days ago
Mon, Feb 1 - Fri, Feb 12
Multiple Airlines Logo
19:40 - 16:25Johannesburg  Johannesburg OR Tambo-Chicago Chicago Midway
28h 45m2 stops Paris Charles de Gaulle Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:30 - 22:00Chicago  Chicago Midway-Johannesburg Johannesburg OR Tambo
25h 30m2 stops Minneapolis St Paul Amsterdam Schiphol
R18 168Multiple Airlines
3+ days ago
Fri, Dec 25 - Mon, Jan 11
Delta Logo
0:30 - 8:50Cape Town  Cape Town Intl-Chicago Chicago Midway
40h 20m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
Delta Logo
13:00 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
21h 35m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
R18 251Delta
3+ days ago
Fri, Dec 25 - Wed, Jan 13
Delta Logo
0:30 - 8:50Cape Town  Cape Town Intl-Chicago Chicago Midway
40h 20m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
Delta Logo
13:00 - 18:35Chicago  Chicago Midway-Cape Town Cape Town Intl
21h 35m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
R18 251Delta
3+ days ago
Mon, Nov 23 - Mon, Dec 7
KLM Logo
23:59 - 18:04Johannesburg  Johannesburg OR Tambo-Chicago Chicago Midway
26h 05m2 stops Amsterdam Schiphol Detroit Metropolitan Wayne County
KLM Logo
12:39 - 22:00Chicago  Chicago Midway-Johannesburg Johannesburg OR Tambo
25h 21m2 stops Minneapolis St Paul Amsterdam Schiphol
R19 162KLM
6 hours ago
Booking Insights

Price, demand, and travel trends for flights to Chicago Midway Airport

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

What is the cheapest flight to Chicago Midway Airport?

Cape Town to Chicago Midway Airport is the cheapest route at R15 134 return, found in the past 5 days on KAYAK. Johannesburg OR Tambo Airport to Chicago Midway Airport is the most popular connection with return deals from R16 991.

How much is a flight to Chicago Midway Airport?

On average, a return flight from South Africa to Chicago Midway Airport costs R18 660, based on KAYAK data over the past 12 months. Return fares from Cape Town average R17 879, while Johannesburg OR Tambo Airport runs a bit higher at R18 175.

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

Evening flights to Chicago Midway Airport are the cheapest at R18 284 return on average. Night flights are the most expensive at R25 146.

What is a good deal for flights to Chicago Midway Airport?

Flights under R16 764 are considered a good deal. 25% of KAYAK users found return flights to Chicago Midway Airport at or below these prices, with the lowest fares from:
•Cape Town R16 392
•Johannesburg OR Tambo Airport R16 733.

Find deals

Key details for flights to Chicago Midway Airport

Cheapest flight

R15 134
The most popular month to fly with an average 11% increase in travellers.
Round-trip flight from Cape Town to Chicago Midway Airport

When to book flights to Midway

Are your dates flexible? Find out the best times to travel to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

Your questions about flights to Chicago Midway Airport, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • How do I know if a flight to Chicago Midway Airport is a good deal?

    A good deal on a flight to Chicago Midway Airport is around R16 764 return. This fare is in the lowest 25% of return flight prices searched on KAYAK, averaged across the cities most often searched as origins by KAYAK users.

  • Which city has the cheapest flights to Chicago Midway Airport?

    Based on fares booked in the past 5 days, the cheapest flights to Chicago Midway Airport are from Johannesburg, starting at R16 991 return.

  • What is the difference between the most popular and the most frequent airline at Chicago Midway Airport?

    Delta operates the most flights from South Africa to Chicago Midway Airport at 0 per week, while Virgin Atlantic is the airline most often selected by KAYAK users searching for flights from South Africa to Chicago Midway Airport. The two are often different because flight volume reflects an airline's schedule, while popularity reflects traveller choice.

  • Which airlines should I consider for flights to Chicago Midway Airport?

    Virgin Atlantic is the most popular airline for KAYAK users flying to Chicago Midway Airport and has the best on-time record at the destination's main airport.

  • Which airports serve Chicago and the surrounding area?

    Flights to Chicago can arrive at several major airports serving the metro area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD). Nearby alternatives within 80,5 km of Chicago include Chicago Midway (MDW). This airport is not in Chicago itself but may be useful depending on your route, airline, and onward travel plans.

Your guide to booking Chicago Midway Airport flights

From booking to airport arrival, find tips to help you plan your flight with more confidence.
  • For flights to Chicago Midway Airport, a good return fare is around R16 764. If you find a fare below that, you're getting a strong deal.
  • If your travel dates are flexible, consider flying to Chicago Midway Airport in September. Return fares historically average R16 626, making September the cheapest month to travel based on KAYAK data from the last 12 months.
  • Before you book:

    • Check the route's typical price range so you can spot a deal.
    • Confirm baggage fees and seat selection costs on budget carriers.
    • Verify whether you need any travel documents beyond an ID.
    • Pick a departure airport, since your nearest may not be the cheapest origin.
  • Shift your departure to afternoon to save up to R6 863 on a return flight. Afternoon flights to Chicago Midway Airport average R18 284 compared to R25 146 for evening flights.
  • Once you arrive in Chicago Midway Airport, a few great places to start are McCormick Place, United Center, and Chicago Riverwalk. These are popular with first-time visitors and can give you a good feel for the area.

Travelling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
New Buffalo
Hammond

More options for your flight to Midway