R2 151+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

Cheapest airline	United Airlines
Good round-trip deal	R5 417 or less
Good one-way deal	R1 839 or less

On average, United Airlines currently has the cheapest one-way flight from Chicago (avg. price of R21 203).

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

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

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 14 June 2025.

Mon 13/1010:15ORD - CPT

1 stop21h 20mEthiopian Air

Thu 23/1013:50CPT - ORD

2 stops25h 25mEthiopian Air

Deal found 13/6R16 907

Tue 30/919:50ORD - CPT

1 stop33h 00mTurkish Airlines

Tue 7/1016:35CPT - ORD

1 stop24h 05mTurkish Airlines

Deal found 14/6R18 090

Fri 31/1021:20ORD - DUR

2 stops36h 45mMultiple Airlines

Sat 8/1112:00DUR - ORD

2 stops30h 10mMultiple Airlines

Deal found 12/6R20 349

Mon 1/910:15ORD - JNB

1 stop19h 50mEthiopian Air

Sun 14/98:20JNB - ORD

2 stops30h 55mEthiopian Air

Deal found 14/6R20 654

Wed 17/919:20ORD - JNB

2 stops36h 00mQatar Airways

Mon 29/913:55JNB - ORD

2 stops48h 08mQatar Airways

Deal found 14/6R20 708

Thu 20/119:45ORD - CPT

2 stops38h 30mMultiple Airlines

Sun 30/115:50CPT - ORD

3 stops33h 50mMultiple Airlines

Deal found 13/6R20 761

Thu 11/97:30ORD - JNB

2 stops33h 55mKenya Airways

Sun 5/101:25JNB - ORD

2 stops42h 13mKenya Airways

Deal found 12/6R20 923

Fri 19/97:30ORD - JNB

2 stops25h 20mMultiple Airlines

Sat 27/917:00JNB - ORD

2 stops26h 10mMultiple Airlines

Deal found 14/6R20 959

Tue 11/1121:45ORD - CPT

1 stop28h 35mBritish Airways

Mon 17/1122:00CPT - ORD

1 stop23h 55mBritish Airways

Deal found 14/6R21 335

Sun 7/919:10ORD - CPT

2 stops32h 50mAmerican Airlines

Sun 14/918:55CPT - ORD

1 stop26h 55mAmerican Airlines

Deal found 13/6R21 425

Thu 4/1216:28ORD - JNB

2 stops31h 02mAmerican Airlines

Wed 17/1222:05JNB - ORD

2 stops26h 49mAmerican Airlines

Deal found 13/6R22 572

Wed 13/811:25ORD - JNB

1 stop40h 10mTurkish Airlines

Fri 22/817:55JNB - ORD

1 stop31h 00mTurkish Airlines

Deal found 13/6R22 608

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 14 June 2025.

Mon 13/1010:15ORD - CPT

1 stop21h 20mEthiopian Air

Thu 23/1013:50CPT - ORD

2 stops25h 25mEthiopian Air

Deal found 13/6R16 907

Tue 30/919:50ORD - CPT

1 stop33h 00mTurkish Airlines

Tue 7/1016:35CPT - ORD

1 stop24h 05mTurkish Airlines

Deal found 14/6R18 090

Fri 31/1021:20ORD - DUR

2 stops36h 45mMultiple Airlines

Sat 8/1112:00DUR - ORD

2 stops30h 10mMultiple Airlines

Deal found 12/6R20 349

Wed 17/919:20ORD - JNB

2 stops36h 00mQatar Airways

Mon 29/913:55JNB - ORD

2 stops48h 08mQatar Airways

Deal found 14/6R20 708

Thu 11/97:30ORD - JNB

2 stops33h 55mKenya Airways

Sun 5/101:25JNB - ORD

2 stops42h 13mKenya Airways

Deal found 12/6R20 923

Tue 11/1121:45ORD - CPT

1 stop28h 35mBritish Airways

Mon 17/1122:00CPT - ORD

1 stop23h 55mBritish Airways

Deal found 14/6R21 335

Sun 7/919:10ORD - CPT

2 stops32h 50mAmerican Airlines

Sun 14/918:55CPT - ORD

1 stop26h 55mAmerican Airlines

Deal found 13/6R21 425

Mon 4/813:55ORD - JNB

1 stop35h 25mEtihad Airways

Tue 12/89:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 13/6R23 773

Sun 24/815:56ORD - CPT

2 stops36h 04mIberia

Mon 8/918:55CPT - ORD

2 stops33h 29mIberia

Deal found 13/6R25 656

Wed 15/1010:35MDW - JNB

1 stop26h 05mDelta

Wed 22/1018:50JNB - MDW

2 stops30h 46mDelta

Deal found 13/6R28 525

Wed 29/1014:00MDW - JNB

2 stops25h 00mKLM

Sun 9/1123:55JNB - MDW

2 stops26h 41mKLM

Deal found 13/6R28 740

Wed 23/720:35ORD - DUR

1 stop37h 00mEmirates

Wed 30/718:40DUR - ORD

1 stop28h 05mEmirates

Deal found 12/6R37 686

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 14 June 2025 and is based on user searches.

Thu 19/610:15ORD - JNB

1 stop19h 50mEthiopian Air

Sun 6/714:30JNB - ORD

2 stops24h 45mEthiopian Air

Deal found 14/6R21 012

Sat 21/611:25ORD - CPT

1 stop41h 25mTurkish Airlines

Fri 11/716:35CPT - ORD

1 stop24h 05mTurkish Airlines

Deal found 14/6R28 811

Sat 21/621:15ORD - CPT

2 stops34h 20mBritish Airways

Fri 11/718:55CPT - ORD

1 stop25h 55mBritish Airways

Deal found 13/6R31 572

Sat 21/618:27ORD - CPT

3 stops60h 13mMultiple Airlines

Fri 11/714:35CPT - ORD

3 stops29h 15mMultiple Airlines

Deal found 14/6R37 292

Sat 21/613:04ORD - CPT

2 stops41h 41mEthiopian Air

Fri 11/714:35CPT - ORD

3 stops30h 58mEthiopian Air

Deal found 14/6R41 379

Sat 21/612:44MDW - CPT

1 stop22h 06mDelta

Fri 11/720:05CPT - MDW

1 stop22h 53mDelta

Deal found 14/6R55 220

Mon 23/617:45ORD - JNB

1 stop30h 15mAmerican Airlines

Wed 9/721:15JNB - ORD

2 stops25h 59mAmerican Airlines

Deal found 14/6R28 542

Mon 23/66:00ORD - JNB

2 stops51h 10mQatar Airways

Mon 7/718:10JNB - ORD

2 stops51h 55mQatar Airways

Deal found 14/6R31 985

Mon 23/613:55ORD - JNB

1 stop35h 25mEtihad Airways

Mon 30/69:50JNB - ORD

1 stop29h 55mEtihad Airways

Deal found 14/6R37 363

Tue 24/619:10ORD - JNB

1 stop28h 50mBritish Airways

Wed 9/721:15JNB - ORD

1 stop23h 40mBritish Airways

Deal found 14/6R27 538

Tue 24/610:15ORD - JNB

1 stop19h 50mMultiple Airlines

Mon 7/71:25JNB - ORD

2 stops42h 25mMultiple Airlines

Deal found 14/6R29 457

Tue 24/67:00ORD - JNB

2 stops44h 55mKenya Airways

Tue 8/712:10JNB - ORD

2 stops31h 40mKenya Airways

Deal found 13/6R30 766

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 14 June 2025.

Tue 2/98:00MDW - JNB

2 stops43h 35mMultiple Airlines

Deal found 14/6R10 721

Tue 2/914:40ORD - JNB

2 stops36h 55mMultiple Airlines

Deal found 14/6R11 044

Tue 2/913:55ORD - JNB

1 stop35h 25mEtihad Airways

Deal found 14/6R11 474

Tue 5/85:01ORD - CPT

3 stops58h 34mMultiple Airlines

Deal found 13/6R12 622

Fri 12/96:15MDW - CPT

3 stops57h 30mMultiple Airlines

Deal found 13/6R13 070

Wed 1/1010:15ORD - CPT

1 stop21h 20mEthiopian Air

Deal found 13/6R13 321

Wed 3/129:45ORD - JNB

1 stop26h 25mEthiopian Air

Deal found 14/6R13 393

Mon 4/823:45ORD - CPT

1 stop29h 05mTurkish Airlines

Deal found 13/6R14 235

Thu 11/1220:20ORD - JNB

1 stop30h 30mTurkish Airlines

Deal found 14/6R14 433

Mon 28/719:50ORD - DUR

2 stops34h 25mTurkish Airlines

Deal found 13/6R15 078

Tue 2/919:20ORD - JNB

2 stops60h 00mRwandAir

Deal found 13/6R15 723

Mon 4/819:05ORD - CPT

2 stops38h 40mSWISS

Deal found 14/6R18 520

Find flights from Chicago within your budget

Fly to

Route

Depart

Return

Price

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Mon 13/10

10:15-14:35

1 stop21h 20m

Cape Town Intl

Thu 23/10

13:50-8:15

2 stops25h 25m

R16 907

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Tue 30/9

19:50-11:50

1 stop33h 00m

Cape Town Intl

Tue 7/10

16:35-9:40

1 stop24h 05m

R18 090

ChicagoDurban

ORD - DUR

ORDDUR

Chicago O'Hare Intl

Fri 31/10

21:20-17:05

2 stops36h 45m

Durban King Shaka Intl

Sat 8/11

12:00-10:10

2 stops30h 10m

R20 349

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Mon 1/9

10:15-13:05

1 stop19h 50m

Johannesburg OR Tambo

Sun 14/9

8:20-8:15

2 stops30h 55m

R20 654

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 17/9

19:20-14:20

2 stops36h 00m

Johannesburg OR Tambo

Mon 29/9

13:55-7:03

2 stops48h 08m

R20 708

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Thu 20/11

9:45-8:15

2 stops38h 30m

Cape Town Intl

Sun 30/11

5:50-7:40

3 stops33h 50m

R20 761

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Fri 19/9

7:30-15:50

2 stops25h 20m

Johannesburg OR Tambo

Sat 27/9

17:00-12:10

2 stops26h 10m

R20 959

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Tue 11/11

21:45-10:20

1 stop28h 35m

Cape Town Intl

Mon 17/11

22:00-13:55

1 stop23h 55m

R21 335

ChicagoCape Town

ORD - CPT

ORDCPT

Chicago O'Hare Intl

Sun 7/9

19:10-11:00

2 stops32h 50m

Cape Town Intl

Sun 14/9

18:55-14:50

1 stop26h 55m

R21 425

ChicagoJohannesburg

ORD - JNB

ORDJNB

Chicago O'Hare Intl

Wed 13/8

11:25-10:35

1 stop40h 10m

Johannesburg OR Tambo

Fri 22/8

17:55-17:55

1 stop31h 00m

R22 608

Flights are sorted by cheapest return flights first.

Deals found on 14/6

Showing 1-10 of 58 results

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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 87 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, November is the cheapest month in which you can book a flight from Chicago (average of R14 522). Flying from Chicago in July will prove the most costly (average of R23 110). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

When flying from Chicago check dates and pricing for the following: United Airlines. As it departs for the following popular destinations: Johannesburg.

United Airlines

United Airlines

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (1 226 flights per day), New York (985 flights per day) and Los Angeles (762 flights per day).

New York

Amsterdam Schiphol

Amsterdam Schiphol

Addis Ababa Bole

Addis Ababa Bole

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Calgary, with prices starting at R1 839. Explore other affordable destinations below.

Calgary

New York

Miami

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

Airline reviews for flights from Chicago

8,1

Very Good

Reviews

1 / 20

4,0

Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

8,1

Very Good

8,1

Very Good

Reviews

1 / 20

4,0

Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

8,0

Very Good

8,1

Very Good

Reviews

1 / 20

4,0

Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

7,8

Good

8,1

Very Good

Reviews

1 / 20

4,0

Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

7,5

Good

8,1

Very Good

Reviews

1 / 20

4,0

Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

7,4

Good

8,1

Very Good

Reviews

1 / 20

4,0

Okay

Anonymous,Dec 2024

IAD - DXB

Not so good. Flight was departed 2 hours late from DC and we missed our connecting flight from Dubai to Mumbai. Our flight Dubai to Mumbai got delayed by three hours. Once we arrived Bombay airport we didnot get all our luggage bags. We were missing two luggage bags so found out that our those two luggage bags are coming in different flight. First they gave us wrong flight information in which our missing luggage coming and wrong phone number to whom we should reach out. I spent hours and hours at the airport to find out our luggage bags. After four five hours later and hectic time at the airport to get our luggage bags. Overall poor communication with emirates staff at the airport and no one is helpful.

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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, Amman. While Atlanta, Boston, Mumbai are the top choices made by travellers year-round.
What is the cheapest month to fly from Chicago?
November 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.
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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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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