Cheap Flights from Cape Town to Chicago
Browse current best options from Cape Town. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Cape Town
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Prices updated 5 days ago
402 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)
Today’s best flight deals from Cape Town to Chicago
Explore current cheapest deals departing from Cape Town to Chicago
Round trip
Sort by: Cheapest
August 2 - August 12
CPT - Chicago
$1,401
$976
Round trip
August 25 - September 6
CPT - Chicago
$1,365
$976
Round trip
August 25 - September 7
CPT - Chicago
$1,369
$976
Round trip
August 25 - September 9
CPT - Chicago
$1,360
$976
Round trip
August 25 - September 10
CPT - Chicago
$1,356
$976
Round trip
August 25 - September 11
CPT - Chicago
$1,351
$976
Round trip
August 25 - September 12
CPT - Chicago
$1,349
$976
Round trip
August 30 - September 6
CPT - Chicago
$1,433
$976
Round trip
August 30 - September 7
CPT - Chicago
$1,392
$976
Round trip
August 30 - September 9
CPT - Chicago
$1,374
$976
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Cape Town to Chicago: Overview
Insights for flights from Cape Town to Chicago
How much is a round trip from Cape Town to Chicago
Regular price: $1,233 - $2,036
Prices for flights from Cape Town to Chicago are currently below the regular range.
The regular price range for this route is between $1233 and $2036. The current lowest deal is $976 via Kayak. This deal is for travel from Aug 2-Aug 12.
now $976
Low $1,233
High $2,036
The cheapest time to fly from Cape Town to Chicago
The cheapest month to fly from Cape Town to Chicago is October, with a median price of $1086. The most expensive month is November, with a median price of $2369. Prices are generally lower from January to October.
October
Flights from $1,086
November
Flights from $2,369
Direct flights from Cape Town to Chicago
United Airlines
Deutsche Luft Hansa
KLM
British Airways
Last-minute flights going from Cape Town to Chicago
Sun, Jul 12
CPT - Chicago
Cape Town (CPT) - Chicago (MDW)
Deutsche Luft Hansa
$1,751
$967
One-way
Sun, Jul 12
CPT - Chicago
Cape Town (CPT) - Chicago (ORD)
$1,399
$969
One-way
Tue, Jul 14
CPT - Chicago
Cape Town (CPT) - Chicago (ORD)
KLM
$1,463
$1,123
One-way
Wed, Jul 15
CPT - Chicago
Cape Town (CPT) - Chicago (ORD)
KLM
$1,463
$983
One-way
Thu, Jul 16
CPT - Chicago
Cape Town (CPT) - Chicago (ORD)
KLM
$1,464
$983
One-way
Thu, Jul 16
CPT - Chicago
Cape Town (CPT) - Chicago (ORD)
United Airlines
$1,463
$1,005
One-way
Biggest price drops on these dates for flights from Cape Town to Chicago
Jul 12 - Jul 27
$1,788 → $967
46%
Aug 4 - Aug 11
$1,811 → $1,117
38%
Jul 24 - Jul 27
$1,448 → $984
32%
Jul 5 - Jul 12
$1,458 → $1,030
29%
Popular Airports to fly from Cape Town to Chicago
Cape Town - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Cape Town to Chicago are below the typical level at $976.
📅 Best time to fly
October is historically cheapest
Historically, October is the cheapest month to fly from Cape Town to Chicago, with a median price of $1086.
⏱️ Flight duration
Long-haul flights, 43h 33m median
Flights from Cape Town to Chicago are long-haul, with a median duration of 43h 33m.
✈️ Airlines & availability
Connecting flights dominant
Connecting flights are dominant on this route, with a median of 3 stopovers.
🏆 Airline highlight
United Airlines has 18 direct deals
United Airlines has 18 direct deals from Cape Town to Chicago, more than other carriers.
🎯 Booking tip
Deals are frequent
Deals for flights from Cape Town to Chicago are frequent, appearing often over 30 days.
Cape Town main airports to depart from
Cape Town International (CPT)
Cape Town International Airport is a good option for flights from Cape Town to Chicago.
📍 ~19 km from city center (reachable by car)
💸 Flights from ~$1007
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub, offering extensive connections for your flight to Chicago.
📍 ~25 km from Chicago city center (reachable by car, train, or bus)
💸 Flights from ~$1007
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient option for reaching downtown Chicago and surrounding areas.
📍 ~15 km from Chicago city center (reachable by car, train, or bus)
💸 Flights from ~$1222
Chicago Rockford International (RFD)
Chicago Rockford International Airport provides an alternative arrival point for the wider Chicago region.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$1666
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International (MKE) is a major international airport with significant carrier presence and direct flight options.
📍 ~135 km from Chicago (reachable by train or car)
💸 Flights from ~$1,213
Gerald R. Ford International (GRR)
Gerald R. Ford International (GRR) is the second largest airport in Michigan with a robust domestic network.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$1,142
Dane County Regional (MSN)
Dane County Regional (MSN) is a reliable regional hub with efficient operations and good amenities.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$1,213
South Bend International (SBN)
South Bend International (SBN) is geographically the closest alternative airport to the Chicago metro area.
📍 ~120 km from Chicago (reachable by train)
💸 Flights from ~$1,447
Fort Wayne International (FWA)
Fort Wayne International (FWA) offers multiple cabin classes and solid connectivity for eastern domestic destinations.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$1,563
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Cape Town to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From CPT
Elite
Sep 06
Chicago, United States
94% AI deal score
$5,892
$3,127
Save $2,765
From CPT
Elite
Sep 20
Chicago, United States
94% AI deal score
$5,799
$3,242
Save $2,557
From CPT
Elite
Sep 02
Chicago, United States
94% AI deal score
$5,879
$3,245
Save $2,634
From CPT
Elite
Sep 12
Chicago, United States
94% AI deal score
$5,883
$3,245
Save $2,638
From CPT
Elite
Sep 09
Chicago, United States
94% AI deal score
$5,900
$3,245
Save $2,655
From CPT
Elite
Sep 05
Chicago, United States
94% AI deal score
$5,892
$3,275
Save $2,617
From CPT
Elite
Sep 22
Chicago, United States
94% AI deal score
$5,853
$3,296
Save $2,557
From CPT
Elite
Nov 08
Chicago, United States
94% AI deal score
$6,273
$3,364
Save $2,909
From CPT
Elite
Nov 04
Chicago, United States
94% AI deal score
$6,316
$3,364
Save $2,952
From CPT
Elite
Nov 07
Chicago, United States
94% AI deal score
$6,296
$3,364
Save $2,932
From CPT
Elite
Nov 23
Chicago, United States
94% AI deal score
$6,243
$3,397
Save $2,846
From CPT
Elite
Aug 03
Chicago, United States
93% AI deal score
$4,927
$3,009
Save $1,918
From CPT
Elite
Aug 07
Chicago, United States
93% AI deal score
$4,947
$3,009
Save $1,938
From CPT
Elite
Aug 02
Chicago, United States
93% AI deal score
$5,153
$3,119
Save $2,034
From CPT
Elite
Aug 05
Chicago, United States
93% AI deal score
$4,947
$3,127
Save $1,820
From CPT
Elite
Jul 06
Chicago, United States
93% AI deal score
$5,372
$3,127
Save $2,245
From CPT
Elite
Aug 30
Chicago, United States
93% AI deal score
$4,985
$3,127
Save $1,858
From CPT
Elite
Aug 14
Chicago, United States
93% AI deal score
$4,979
$3,127
Save $1,852
From CPT
Elite
Jul 22
Chicago, United States
93% AI deal score
$5,446
$3,127
Save $2,319
From CPT
Elite
Aug 10
Chicago, United States
93% AI deal score
$4,947
$3,127
Save $1,820
From CPT
Elite
Jul 07
Chicago, United States
93% AI deal score
$5,375
$3,127
Save $2,248
From CPT
Elite
Aug 20
Chicago, United States
93% AI deal score
$4,989
$3,127
Save $1,862
From CPT
Elite
Aug 09
Chicago, United States
93% AI deal score
$4,947
$3,127
Save $1,820
From CPT
Elite
Aug 09
Chicago, United States
93% AI deal score
$4,836
$3,144
Save $1,692
From CPT
Elite
Jul 05
Chicago, United States
93% AI deal score
$5,377
$3,153
Save $2,224
From CPT
Elite
Jul 14
Chicago, United States
93% AI deal score
$5,430
$3,240
Save $2,190
From CPT
Elite
Jul 28
Chicago, United States
93% AI deal score
$5,446
$3,242
Save $2,204
From CPT
Elite
Aug 01
Chicago, United States
93% AI deal score
$5,151
$3,242
Save $1,909
From CPT
Elite
Jul 18
Chicago, United States
93% AI deal score
$5,294
$3,242
Save $2,052
From CPT
Elite
Aug 25
Chicago, United States
93% AI deal score
$4,987
$3,245
Save $1,742
From CPT
Elite
Aug 06
Chicago, United States
93% AI deal score
$4,947
$3,245
Save $1,702
From CPT
Elite
Jul 20
Chicago, United States
93% AI deal score
$5,446
$3,245
Save $2,201
From CPT
Elite
Jul 12
Chicago, United States
93% AI deal score
$5,383
$3,245
Save $2,138
From CPT
Elite
Jul 26
Chicago, United States
93% AI deal score
$5,446
$3,245
Save $2,201
From CPT
Elite
Aug 26
Chicago, United States
93% AI deal score
$4,987
$3,245
Save $1,742
From CPT
Elite
Jul 23
Chicago, United States
93% AI deal score
$5,446
$3,245
Save $2,201
From CPT
Elite
Aug 19
Chicago, United States
93% AI deal score
$4,989
$3,245
Save $1,744
From CPT
Elite
Dec 02
Chicago, United States
93% AI deal score
$5,391
$3,245
Save $2,146
From CPT
Elite
Jul 03
Chicago, United States
93% AI deal score
$5,383
$3,268
Save $2,115
From CPT
Elite
Jul 04
Chicago, United States
93% AI deal score
$5,386
$3,268
Save $2,118
From CPT
Elite
Jul 15
Chicago, United States
93% AI deal score
$5,432
$3,275
Save $2,157
From CPT
Elite
Jul 24
Chicago, United States
93% AI deal score
$5,446
$3,279
Save $2,167
From CPT
Elite
Sep 16
Chicago, United States
93% AI deal score
$5,810
$3,364
Save $2,446
From CPT
Elite
Sep 23
Chicago, United States
93% AI deal score
$5,839
$3,386
Save $2,453
From CPT
Elite
Dec 05
Chicago, United States
93% AI deal score
$5,441
$3,397
Save $2,044
From CPT
Elite
Sep 22
Chicago, United States
93% AI deal score
$5,813
$3,558
Save $2,255
From CPT
Elite
Oct 07
Chicago, United States
92% AI deal score
$6,782
$3,245
Save $3,537
From CPT
Elite
Oct 28
Chicago, United States
92% AI deal score
$6,813
$3,245
Save $3,568
From CPT
Elite
Aug 10
Chicago, United States
92% AI deal score
$4,836
$3,270
Save $1,566
From CPT
Elite
Jul 04
Chicago, United States
92% AI deal score
$5,330
$3,271
Save $2,059
From CPT
Elite
Oct 26
Chicago, United States
92% AI deal score
$6,813
$3,279
Save $3,534
From CPT
Elite
Aug 04
Chicago, United States
92% AI deal score
$4,837
$3,284
Save $1,553
From CPT
Elite
Aug 19
Chicago, United States
92% AI deal score
$4,894
$3,292
Save $1,602
From CPT
Elite
Aug 08
Chicago, United States
92% AI deal score
$4,947
$3,306
Save $1,641
From CPT
Elite
Jun 30
Chicago, United States
92% AI deal score
$5,437
$3,336
Save $2,101
From CPT
Elite
Jul 19
Chicago, United States
92% AI deal score
$5,446
$3,364
Save $2,082
From CPT
Elite
Jul 29
Chicago, United States
92% AI deal score
$5,450
$3,364
Save $2,086
From CPT
Elite
Jul 31
Chicago, United States
92% AI deal score
$5,448
$3,364
Save $2,084
From CPT
Elite
Jul 27
Chicago, United States
92% AI deal score
$5,446
$3,364
Save $2,082
From CPT
Elite
Jul 30
Chicago, United States
92% AI deal score
$5,450
$3,364
Save $2,086
From CPT
Elite
Jul 18
Chicago, United States
92% AI deal score
$5,446
$3,364
Save $2,082
From CPT
Elite
Jul 22
Chicago, United States
92% AI deal score
$5,437
$3,376
Save $2,061
From CPT
Elite
Aug 05
Chicago, United States
92% AI deal score
$4,836
$3,381
Save $1,455
From CPT
Elite
Aug 12
Chicago, United States
92% AI deal score
$4,869
$3,388
Save $1,481
From CPT
Elite
Jul 29
Chicago, United States
92% AI deal score
$5,408
$3,388
Save $2,020
From CPT
Elite
Jun 25
Chicago, United States
92% AI deal score
$5,552
$3,392
Save $2,160
From CPT
Elite
Jul 08
Chicago, United States
92% AI deal score
$5,374
$3,392
Save $1,982
From CPT
Elite
Aug 24
Chicago, United States
92% AI deal score
$4,995
$3,397
Save $1,598
From CPT
Elite
Jul 09
Chicago, United States
92% AI deal score
$5,421
$3,397
Save $2,024
From CPT
Elite
Aug 31
Chicago, United States
92% AI deal score
$5,017
$3,397
Save $1,620
From CPT
Elite
Jun 22
Chicago, United States
92% AI deal score
$5,675
$3,417
Save $2,258
From CPT
Elite
Jun 24
Chicago, United States
92% AI deal score
$5,562
$3,513
Save $2,049
From CPT
Elite
Jul 16
Chicago, United States
92% AI deal score
$5,446
$3,517
Save $1,929
From CPT
Elite
Nov 11
Chicago, United States
91% AI deal score
$6,255
$3,242
Save $3,013
From CPT
Elite
Nov 18
Chicago, United States
91% AI deal score
$6,239
$3,242
Save $2,997
From CPT
Elite
Nov 27
Chicago, United States
91% AI deal score
$6,143
$3,245
Save $2,898
From CPT
Elite
Nov 29
Chicago, United States
91% AI deal score
$6,165
$3,245
Save $2,920
From CPT
Elite
Jun 22
Chicago, United States
89% AI deal score
$2,389
$1,802
Save $587
From CPT
Elite
Oct 13
Chicago, United States
75% AI deal score
$6,979
From CPT
Elite
Jun 21
Chicago, United States
75% AI deal score
$2,712
From CPT
Elite
Jul 17
Chicago, United States
75% AI deal score
$2,774
From CPT
Elite
Jul 21
Chicago, United States
75% AI deal score
$2,830
From CPT
Elite
Nov 23
Chicago, United States
74% AI deal score
$2,774
From CPT
Elite
Oct 27
Chicago, United States
74% AI deal score
$3,622
From CPT
Elite
Oct 26
Chicago, United States
74% AI deal score
$3,622
From CPT
Elite
Oct 20
Chicago, United States
74% AI deal score
$3,622
From CPT
Elite
Oct 23
Chicago, United States
74% AI deal score
$3,622
From CPT
Elite
Oct 05
Chicago, United States
74% AI deal score
$3,684
From CPT
Elite
Oct 06
Chicago, United States
74% AI deal score
$3,684
From CPT
Elite
Nov 04
Chicago, United States
73% AI deal score
$3,622
From CPT
Elite
Nov 01
Chicago, United States
73% AI deal score
$3,622
From CPT
Elite
Nov 03
Chicago, United States
73% AI deal score
$3,622
From CPT
Elite
Jul 27
Chicago, United States
73% AI deal score
$3,650
From CPT
Elite
Dec 02
Chicago, United States
73% AI deal score
$3,663
From CPT
Elite
Sep 22
Chicago, United States
73% AI deal score
$3,684
From CPT
Elite
Jul 16
Chicago, United States
73% AI deal score
$3,736
From CPT
Elite
Jul 16
Chicago, United States
73% AI deal score
$3,739
From CPT
Elite
Sep 16
Chicago, United States
73% AI deal score
$3,740
From CPT
Elite
Sep 08
Chicago, United States
73% AI deal score
$3,740
From CPT
Elite
Jul 23
Chicago, United States
73% AI deal score
$3,740