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$169+ 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 1/5. 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.
CHI — AKL
28 Mar — 4 Apr1
1 adult

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 23 March 2025.

Good round-trip deal

$526 or less

Good one-way deal

$175 or less
Price to beat on a round-trip flight from Chicago.
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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 23 March 2025.

Wed 7/509:55ORD - MIA
Nonstop3h 15mSpirit Airlines
Wed 14/514:29MIA - ORD
1 stop6h 38mSpirit Airlines
Deal found 23/3$201
Sat 3/510:37ORD - MIA
Nonstop3h 19mUnited Airlines
Tue 6/512:20MIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 23/3$309
Sat 26/409:15ORD - PHX
Nonstop4h 06mUnited Airlines
Sat 3/507:00PHX - ORD
Nonstop3h 31mUnited Airlines
Deal found 23/3$312
Sat 3/510:50ORD - MIA
1 stop8h 09mJetBlue
Tue 6/506:00MIA - ORD
1 stop10h 04mJetBlue
Deal found 23/3$344
Tue 6/506:00ORD - PHX
1 stop8h 54mAlaska Airlines
Tue 13/509:00PHX - ORD
1 stop7h 20mAlaska Airlines
Deal found 22/3$361
Mon 19/509:00ORD - MIA
1 stop8h 07mDelta
Sat 24/508:10MIA - ORD
1 stop7h 56mDelta
Deal found 22/3$378
Tue 22/407:30ORD - PHX
1 stop8h 30mSouthwest
Tue 29/416:50PHX - ORD
Nonstop3h 30mSouthwest
Deal found 23/3$380
Wed 7/506:00ORD - PHX
1 stop10h 12mHawaiian Airlines
Sat 10/509:00PHX - ORD
1 stop8h 10mHawaiian Airlines
Deal found 23/3$394
Sat 3/507:25ORD - PHX
1 stop6h 44mDelta
Fri 9/500:45PHX - ORD
1 stop5h 49mDelta
Deal found 23/3$413
Thu 18/919:12ORD - PHX
1 stop14h 38mSun Country Air
Fri 26/909:34PHX - ORD
1 stop7h 02mSun Country Air
Deal found 22/3$445
Sun 20/407:30ORD - MIA
1 stop10h 25mSouthwest
Tue 22/407:35MIA - ORD
1 stop8h 25mSouthwest
Deal found 22/3$453
Fri 11/419:05ORD - MIA
1 stop23h 18mSun Country Air
Sun 13/411:37MIA - ORD
1 stop24h 16mSun Country Air
Deal found 23/3$602

Find flights from Chicago within your budget

Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 23 March 2025. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Auckland

Route

Departure

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 3/5

10:37-14:56

Nonstop3h 19m

Miami

Tue 6/5

12:20-14:54

Nonstop3h 34m

$309

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 23/4

13:10-15:13

Nonstop4h 03m

Phoenix Sky Harbor Intl

Mon 28/4

00:45-06:12

Nonstop3h 27m

$312

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 7/5

05:51-13:06

1 stop6h 15m

Miami

Wed 14/5

12:00-07:27

2 stops20h 27m

$321

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 22/4

13:31-23:55

1 stop9h 24m

Miami

Sun 27/4

10:20-19:27

1 stop10h 07m

$344

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 16/6

09:00-17:10

1 stop7h 10m

Miami

Sat 28/6

08:11-12:49

1 stop5h 38m

$378

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 22/4

07:30-14:00

1 stop8h 30m

Phoenix Sky Harbor Intl

Tue 29/4

16:50-22:20

Nonstop3h 30m

$380

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 6/5

06:00-12:54

1 stop8h 54m

Phoenix Sky Harbor Intl

Wed 7/5

09:00-18:20

1 stop7h 20m

$394

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 7/5

13:40-18:02

1 stop6h 22m

Phoenix Sky Harbor Intl

Tue 13/5

00:45-08:24

1 stop5h 39m

$413

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 22/4

15:44-23:59

1 stop10h 15m

Phoenix Sky Harbor Intl

Tue 29/4

06:00-18:01

1 stop10h 01m

$424

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 27/5

07:30-17:25

2 stops8h 55m

Miami

Sat 31/5

06:50-12:45

1 stop6h 55m

$457

Flights are sorted by cheapest return flights first.

Deals found on 23/3

Showing 1-10 of 60 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.

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

Currently, August is the cheapest month in which you can book a flight from Chicago (average of $380). Flying from Chicago in December will prove the most costly (average of $2,014). 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?

Some of the most frequent flights departing from Chicago everyday are: New York (1,467 flights per day), Detroit (1,090 flights per day), and Los Angeles (588 flights per day).

Los Angeles

Los Angeles

From $49

Miami

Miami

From $182

Toronto

Toronto

From $302

San Francisco

San Francisco

From $100

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Los Angeles, with prices starting at $85. Explore other affordable destinations below.

Los Angeles

Los Angeles

From $49

San Francisco

San Francisco

From $100

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

Las Vegas Harry Reid Intl

Las Vegas Harry Reid Intl

From $155

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 134,765 searches.
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Food

7.8

Boarding

8.7

Overall

8.7

Entertainment

7.2

Crew

9.1

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Air Tahiti Nui
8.7
Very Good
61 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Food

7.8

Boarding

8.7

Overall

8.7

Entertainment

7.2

Crew

9.1

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
EVA Air
8.4
Very Good
1,168 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Food

7.8

Boarding

8.7

Overall

8.7

Entertainment

7.2

Crew

9.1

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Fiji Airways
8.0
Very Good
182 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Food

7.8

Boarding

8.7

Overall

8.7

Entertainment

7.2

Crew

9.1

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Air New Zealand
7.9
Good
454 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Food

7.8

Boarding

8.7

Overall

8.7

Entertainment

7.2

Crew

9.1

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Qantas Airways
7.5
Good
809 reviews
Air Tahiti Nui
8.7
Very Good
61 reviews
Check prices

Comfort

8.0

Food

7.8

Boarding

8.7

Overall

8.7

Entertainment

7.2

Crew

9.1

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 23 March 2025.

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

    The most popular destinations from Chicago this month are Atlanta, Boston, Barcelona-El Prat Airport. The top year-round destinations include Atlanta, Boston, Athens.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently August; with December being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago?

    Here are some of the cheapest flight destinations from Chicago:
    Fly from Chicago to Auckland from $1,714 round trip

  • How does Cheapflights help users find flights from Chicago?

    900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

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

    Cheapflights simply makes it quick and affordable to book flights from Chicago by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

  • Can Cheapflights find flights from Chicago with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

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

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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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?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

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

Cheapflights simply makes it quick and affordable to book flights from Chicago by bringing together all flight options from hundreds of airlines and agencies online — and we put them in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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