What are the most popular destinations to fly to from Chicago?

The most selected flight destinations from Chicago for the current month are Athens, Boston, Atlanta. While Atlanta, Boston, Ahmedabad are the top choices made by travellers year-round.

What are the cheapest airlines flying from Chicago to anywhere?

Looking at our data, United Airlines, Turkish Airlines, and Ethiopian Air have been found to have the cheapest prices from Chicago. Here are some options available: United Airlines flights from Chicago to Johannesburg OR Tambo (R13 705). Turkish Airlines flights from Chicago to Johannesburg OR Tambo (R14 683). Ethiopian Air flights from Chicago to Johannesburg OR Tambo (R15 447).

What is the cheapest month to fly from Chicago?

January is currently the cheapest month to fly from Chicago . At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

Where are the cheapest places to fly to from Chicago?

Check out the cheapest flights from Chicago to embark to: Travel from Chicago to Cape Town from R16 849 round trip

R2 013+ Cheap Flights from Chicago

What to know about flights from Chicago

Good round-trip deal	R5 243 or less
Good one-way deal	R771 or less

Price to beat on a round-trip flight from Chicago.

Search Deals

Price to beat on a one-way flight from Chicago.

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Find flights from Chicago

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 16 September 2025.

Wed 15/1010:15ORD - JNB

1 stop19h 50mEthiopian Air

Thu 23/108:20JNB - ORD

2 stops30h 55mEthiopian Air

Deal found 14/9R15 652

Thu 23/1010:15ORD - JNB

1 stop19h 50mEthiopian Air

Sun 2/1114:30JNB - ORD

2 stops25h 10mEthiopian Air

Deal found 13/9R16 173

Sun 12/1010:15ORD - JNB

1 stop26h 55mEthiopian Air

Thu 23/1014:30JNB - ORD

2 stops24h 45mEthiopian Air

Deal found 14/9R16 346

Tue 3/310:40ORD - JNB

2 stops45h 10mMultiple Airlines

Mon 9/31:35JNB - ORD

2 stops47h 02mMultiple Airlines

Deal found 15/9R16 728

Sun 28/910:15ORD - JNB

1 stop19h 50mEthiopian Air

Wed 8/108:20JNB - ORD

2 stops30h 55mEthiopian Air

Deal found 15/9R16 832

Wed 29/1019:50ORD - JNB

2 stops39h 50mQatar Airways

Wed 5/1113:45JNB - ORD

1 stop32h 45mQatar Airways

Deal found 13/9R16 849

Thu 30/1010:15ORD - JNB

1 stop19h 50mEthiopian Air

Thu 6/1114:30JNB - ORD

2 stops25h 10mEthiopian Air

Deal found 15/9R17 162

Wed 4/220:20ORD - CPT

1 stop31h 30mTurkish Airlines

Wed 11/217:15CPT - ORD

1 stop24h 50mTurkish Airlines

Deal found 15/9R17 283

Wed 5/119:45ORD - CPT

1 stop20h 50mEthiopian Air

Wed 19/1114:35CPT - ORD

2 stops25h 05mEthiopian Air

Deal found 15/9R17 318

Sun 28/910:15ORD - JNB

1 stop26h 55mEthiopian Air

Sun 5/1014:30JNB - ORD

2 stops24h 45mEthiopian Air

Deal found 15/9R17 353

Wed 5/119:45ORD - CPT

1 stop20h 50mEthiopian Air

Thu 20/1113:50CPT - ORD

2 stops25h 50mEthiopian Air

Deal found 15/9R17 491

Thu 15/118:50ORD - JNB

2 stops39h 50mQatar Airways

Sat 31/113:45JNB - ORD

1 stop32h 45mQatar Airways

Deal found 14/9R17 526

Best flights from Chicago
Discover carefully curated flight deals from Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 16 September 2025.

Fri 16/19:45ORD - CPT

1 stop20h 50mEthiopian Air

Sun 25/113:50CPT - ORD

2 stops25h 50mEthiopian Air

Deal found 15/9R17 943

Sun 23/117:00ORD - JNB

2 stops24h 50mMultiple Airlines

Sun 7/121:35JNB - ORD

2 stops43h 08mMultiple Airlines

Deal found 15/9R18 810

Sun 23/1118:50ORD - JNB

2 stops39h 50mQatar Airways

Mon 8/1213:45JNB - ORD

1 stop32h 45mQatar Airways

Deal found 15/9R19 192

Mon 10/1111:50ORD - CPT

1 stop40h 00mTurkish Airlines

Fri 21/1117:15CPT - ORD

1 stop33h 10mTurkish Airlines

Deal found 13/9R19 504

Thu 15/113:10ORD - JNB

1 stop35h 10mEtihad Airways

Sat 31/19:50JNB - ORD

1 stop30h 05mEtihad Airways

Deal found 14/9R21 951

Wed 5/1116:06ORD - CPT

2 stops31h 59mBritish Airways

Mon 17/1122:10CPT - ORD

1 stop23h 40mBritish Airways

Deal found 15/9R22 888

Thu 6/1117:09MDW - CPT

1 stop18h 06mVirgin Atlantic

Thu 20/1121:30CPT - MDW

1 stop27h 08mVirgin Atlantic

Deal found 16/9R23 964

Mon 10/1110:00ORD - CPT

2 stops22h 10mUnited Airlines

Fri 21/1120:50CPT - ORD

2 stops25h 50mUnited Airlines

Deal found 15/9R24 033

Thu 6/1113:48MDW - CPT

2 stops21h 27mDelta

Thu 20/1121:30CPT - MDW

2 stops23h 04mDelta

Deal found 15/9R24 033

Sat 8/1113:25ORD - CPT

2 stops24h 30mKLM

Wed 19/1123:45CPT - ORD

2 stops26h 41mKLM

Deal found 15/9R24 467

Sun 28/910:15ORD - JNB

1 stop26h 55mEthiopian Air

Sat 11/108:20JNB - ORD

2 stops30h 55mEthiopian Air

Deal found 15/9R18 220

Mon 29/920:35ORD - PLZ

2 stops40h 25mEmirates

Thu 2/108:15PLZ - ORD

2 stops38h 30mEmirates

Deal found 16/9R37 776

Wed 15/1010:15ORD - DUR

2 stops25h 55mMultiple Airlines

Wed 22/1010:20DUR - ORD

3 stops28h 55mMultiple Airlines

Deal found 15/9R18 932

Wed 29/1021:20ORD - DUR

2 stops33h 10mTurkish Airlines

Wed 5/1116:00DUR - ORD

2 stops34h 25mTurkish Airlines

Deal found 13/9R19 539

Sun 12/1019:40ORD - JNB

1 stop37h 30mQatar Airways

Sat 18/103:10JNB - ORD

2 stops42h 40mQatar Airways

Deal found 16/9R20 250

Mon 24/1120:20ORD - JNB

1 stop30h 30mTurkish Airlines

Mon 8/1219:05JNB - ORD

1 stop31h 20mTurkish Airlines

Deal found 15/9R19 678

Mon 29/910:15ORD - JNB

1 stop19h 50mEthiopian Air

Mon 6/1022:50JNB - ORD

2 stops40h 25mEthiopian Air

Deal found 15/9R19 955

Wed 29/1010:15ORD - DUR

2 stops24h 50mMultiple Airlines

Wed 5/118:10DUR - ORD

3 stops31h 30mMultiple Airlines

Deal found 13/9R20 441

Sat 22/1118:50ORD - JNB

2 stops39h 50mQatar Airways

Mon 8/1213:45JNB - ORD

1 stop32h 45mQatar Airways

Deal found 15/9R20 476

Tue 4/1116:06ORD - CPT

2 stops31h 59mBritish Airways

Mon 17/1120:35CPT - ORD

1 stop30h 10mBritish Airways

Deal found 13/9R22 888

Tue 4/1111:50ORD - CPT

1 stop40h 00mTurkish Airlines

Thu 20/1117:15CPT - ORD

1 stop24h 50mTurkish Airlines

Deal found 15/9R19 851

Sun 28/910:15ORD - JNB

1 stop19h 50mEthiopian Air

Mon 6/1022:50JNB - ORD

2 stops40h 25mEthiopian Air

Deal found 15/9R19 955

Thu 6/1119:40ORD - CPT

2 stops32h 30mBritish Airways

Mon 17/1122:10CPT - ORD

1 stop23h 40mBritish Airways

Deal found 15/9R23 756

Sun 4/117:00MDW - CPT

1 stop18h 15mVirgin Atlantic

Sun 18/121:30CPT - MDW

1 stop26h 55mVirgin Atlantic

Deal found 16/9R26 168

Tue 4/1120:20ORD - CPT

1 stop31h 30mTurkish Airlines

Fri 21/1117:15CPT - ORD

1 stop24h 50mTurkish Airlines

Deal found 13/9R20 372

Mon 29/910:35MDW - JNB

1 stop26h 05mDelta

Wed 8/1021:55JNB - MDW

1 stop25h 14mDelta

Deal found 15/9R27 348

Sat 27/910:15ORD - JNB

1 stop19h 50mEthiopian Air

Mon 6/1022:50JNB - ORD

2 stops40h 25mEthiopian Air

Deal found 15/9R20 823

Wed 5/1113:08MDW - JNB

2 stops24h 57mKLM

Thu 13/1123:59JNB - MDW

2 stops26h 19mKLM

Deal found 14/9R27 851

Sun 4/112:43MDW - CPT

1 stop22h 32mDelta

Sun 18/121:30CPT - MDW

1 stop20h 26mDelta

Deal found 14/9R27 348

Wed 29/1017:04MDW - CPT

1 stop19h 11mVirgin Atlantic

Mon 10/1121:30CPT - MDW

1 stop27h 08mVirgin Atlantic

Deal found 15/9R27 348

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 16 September 2025 and is based on user searches.

Sun 21/910:15ORD - DUR

2 stops24h 50mEthiopian Air

Wed 24/98:10DUR - ORD

3 stops55h 05mEthiopian Air

Deal found 14/9R27 035

Mon 22/910:15ORD - JNB

1 stop19h 50mEthiopian Air

Thu 2/108:20JNB - ORD

2 stops30h 55mEthiopian Air

Deal found 14/9R16 832

Mon 22/919:20ORD - JNB

1 stop31h 15mQatar Airways

Wed 1/103:10JNB - ORD

2 stops42h 40mQatar Airways

Deal found 16/9R19 643

Mon 22/96:45ORD - JNB

2 stops34h 40mMultiple Airlines

Thu 2/1017:00JNB - ORD

2 stops26h 16mMultiple Airlines

Deal found 16/9R20 823

Mon 22/913:55ORD - JNB

1 stop35h 25mEtihad Airways

Thu 2/109:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 14/9R23 044

Mon 22/923:45ORD - JNB

1 stop27h 50mTurkish Airlines

Thu 2/1017:50JNB - ORD

1 stop22h 50mTurkish Airlines

Deal found 14/9R23 339

Tue 23/911:13ORD - CPT

2 stops51h 57mMultiple Airlines

Tue 30/914:30CPT - ORD

3 stops33h 21mMultiple Airlines

Deal found 15/9R23 218

Tue 23/919:50ORD - CPT

1 stop33h 00mTurkish Airlines

Tue 30/916:35CPT - ORD

1 stop24h 05mTurkish Airlines

Deal found 15/9R25 682

Thu 25/910:15ORD - JNB

1 stop34h 40mEthiopian Air

Tue 28/1014:30JNB - ORD

2 stops25h 10mEthiopian Air

Deal found 16/9R18 533

Thu 25/913:55ORD - JNB

1 stop35h 25mEtihad Airways

Tue 28/109:50JNB - ORD

1 stop30h 05mEtihad Airways

Deal found 16/9R23 842

Thu 25/910:15ORD - CPT

2 stops29h 20mMultiple Airlines

Mon 13/1016:35CPT - ORD

1 stop24h 05mMultiple Airlines

Deal found 14/9R26 324

Fri 26/910:15ORD - CPT

1 stop21h 20mEthiopian Air

Sat 11/1015:25CPT - ORD

2 stops47h 50mEthiopian Air

Deal found 15/9R22 281

One-way flights from Chicago
Search for one-way flight options from Chicago. Find affordable one-way fares based on user searches. Data last updated 16 September 2025.

Sat 6/1218:24ORD - JNB

2 stops53h 56mMultiple Airlines

Deal found 15/9R10 759

Tue 23/911:45ORD - CPT

3 stops51h 25mMultiple Airlines

Deal found 13/9R11 158

Sun 21/920:49ORD - CPT

3 stops42h 21mMultiple Airlines

Deal found 13/9R11 418

Wed 3/126:40ORD - JNB

2 stops40h 30mMultiple Airlines

Deal found 15/9R11 973

Thu 4/125:10ORD - JNB

2 stops45h 40mMultiple Airlines

Deal found 15/9R12 234

Thu 20/116:00ORD - JNB

2 stops44h 50mMultiple Airlines

Deal found 15/9R12 424

Thu 25/911:13ORD - CPT

3 stops49h 32mMultiple Airlines

Deal found 15/9R12 459

Fri 26/918:11ORD - CPT

3 stops57h 49mMultiple Airlines

Deal found 15/9R12 650

Wed 1/1010:15ORD - CPT

1 stop21h 20mEthiopian Air

Deal found 14/9R13 119

Fri 5/1218:24ORD - JNB

2 stops56h 26mMultiple Airlines

Deal found 15/9R13 205

Wed 24/910:15ORD - CPT

1 stop21h 20mEthiopian Air

Deal found 13/9R13 292

Mon 1/129:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 15/9R13 361

Fly to

Route

Depart

Return

Price

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Fri 16/1

9:45-14:35

1 stop20h 50m

Cape Town Intl

Sun 25/1

13:50-7:40

2 stops25h 50m

R17 943

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 28/9

10:15-20:10

1 stop26h 55m

Johannesburg OR Tambo

Sat 11/10

8:20-8:15

2 stops30h 55m

R18 220

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 23/11

7:00-15:50

2 stops24h 50m

Johannesburg OR Tambo

Sun 7/12

1:35-12:43

2 stops43h 08m

R18 810

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Wed 15/10

10:15-19:10

2 stops25h 55m

Durban King Shaka Intl

Wed 22/10

10:20-8:15

3 stops28h 55m

R18 932

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Sun 23/11

18:50-18:40

2 stops39h 50m

Johannesburg OR Tambo

Mon 8/12

13:45-14:30

1 stop32h 45m

R19 192

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 10/11

11:50-11:50

1 stop40h 00m

Cape Town Intl

Fri 21/11

17:15-18:25

1 stop33h 10m

R19 504

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Wed 29/10

21:20-13:30

2 stops33h 10m

Durban King Shaka Intl

Wed 5/11

16:00-18:25

2 stops34h 25m

R19 539

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 24/11

20:20-10:50

1 stop30h 30m

Johannesburg OR Tambo

Mon 8/12

19:05-18:25

1 stop31h 20m

R19 678

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Tue 4/11

11:50-11:50

1 stop40h 00m

Cape Town Intl

Thu 20/11

17:15-10:05

1 stop24h 50m

R19 851

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 29/9

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Mon 6/10

22:50-8:15

2 stops40h 25m

R19 955

Flights are sorted by cheapest return flights first.

Deals found on 15/9

Showing 1-10 of 60 results

...

Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.

Estimated return price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago?

Booking 16 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago?

Currently, January is the cheapest month in which you can book a flight from Chicago (average of R13 257). Flying from Chicago in July will prove the most costly (average of R26 515). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1 680 flights per day), Detroit (1 254 flights per day) and Los Angeles (781 flights per day).

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Charlotte Douglas, with prices starting at R771. Explore other affordable destinations below.

Browse thousands of different options on Cheapflights for your next trip

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Related info for your journey

What are the most popular destinations to fly to from Chicago?
The most selected flight destinations from Chicago for the current month are Athens, Boston, Atlanta. While Atlanta, Boston, Ahmedabad are the top choices made by travellers year-round.
What are the cheapest airlines flying from Chicago to anywhere?
Looking at our data, United Airlines, Turkish Airlines, and Ethiopian Air have been found to have the cheapest prices from Chicago. Here are some options available: United Airlines flights from Chicago to Johannesburg OR Tambo (R13 705). Turkish Airlines flights from Chicago to Johannesburg OR Tambo (R14 683). Ethiopian Air flights from Chicago to Johannesburg OR Tambo (R15 447).
What is the cheapest month to fly from Chicago?
January is currently the cheapest month to fly from Chicago. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.
Where are the cheapest places to fly to from Chicago?
Check out the cheapest flights from Chicago to embark to:
Travel from Chicago to Cape Town from R16 849 round trip
How does Cheapflights help users find flights from Chicago?
Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Chicago?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.
Can Cheapflights find flights from Chicago with no change fees?
Certainly. Search results for flights from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Can Cheapflights notify me if prices for flights from Chicago become cheaper?
Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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Fly with Cheapflights

How does Cheapflights help users find flights from Chicago?

Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Certainly. Search results for flights from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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R2 013+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.

What to know about flights from Chicago

Good round-trip deal

Good one-way deal

Find flights from Chicago

Cheapest flights from ChicagoExplore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 16 September 2025.

Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 16 September 2025.

Find flights from Chicago within your budget

Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago?

Use this chart to determine the optimal time to book a return flight from Chicago to Cape Town. Price data was last updated on 12 September 2025.

What is the cheapest month to book a flight from Chicago?

What are popular destinations to fly to from Chicago?

What is the cheapest place to fly to from Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.

Related info for your journey

What are the most popular destinations to fly to from Chicago?

What are the cheapest airlines flying from Chicago to anywhere?

What is the cheapest month to fly from Chicago?

Where are the cheapest places to fly to from Chicago?

How does Cheapflights help users find flights from Chicago?

Why should you use Cheapflights to find cheap flight tickets from Chicago?

Can Cheapflights find flights from Chicago with no change fees?

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago?

Why should you use Cheapflights to find cheap flight tickets from Chicago?

Can Cheapflights find flights from Chicago with no change fees?

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

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Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 16 September 2025.