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$172+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/5. 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
16 Apr — 23 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 11 April 2025.

Good round-trip deal

$520 or less

Good one-way deal

$267 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 11 April 2025.

Thu 8/507:35ORD - PHX
Nonstop4h 07mFrontier
Mon 12/510:40PHX - ORD
Nonstop3h 33mFrontier
Deal found 10/4$309
Thu 8/521:02ORD - PHX
1 stop13h 11mMultiple Airlines
Mon 12/510:40PHX - ORD
Nonstop3h 33mMultiple Airlines
Deal found 10/4$319
Tue 6/516:05ORD - PHX
Nonstop4h 02mUnited Airlines
Tue 13/514:35PHX - ORD
Nonstop3h 30mUnited Airlines
Deal found 11/4$326
Sat 3/512:00ORD - PHX
1 stop8h 47mHawaiian Airlines
Sat 10/509:00PHX - ORD
1 stop8h 10mHawaiian Airlines
Deal found 11/4$376
Thu 8/521:02ORD - PHX
1 stop13h 11mSpirit Airlines
Mon 12/509:19PHX - ORD
2 stops19h 23mSpirit Airlines
Deal found 10/4$390
Sat 31/507:00ORD - PHX
1 stop8h 05mAlaska Airlines
Tue 3/615:43PHX - ORD
1 stop11h 57mAlaska Airlines
Deal found 11/4$407
Sat 10/515:33ORD - PHX
1 stop6h 35mDelta
Fri 16/500:45PHX - ORD
1 stop5h 49mDelta
Deal found 11/4$409
Wed 14/514:50ORD - PHX
Nonstop3h 50mSouthwest
Mon 19/505:20PHX - ORD
1 stop9h 05mSouthwest
Deal found 11/4$438
Mon 25/806:00ORD - SJU
1 stop6h 29mDelta
Fri 5/914:15SJU - ORD
1 stop7h 19mDelta
Deal found 11/4$529
Sat 13/912:45ORD - SJU
1 stop10h 12mUnited Airlines
Sat 20/901:05SJU - ORD
1 stop7h 26mUnited Airlines
Deal found 10/4$552
Wed 7/516:03ORD - SJU
1 stop8h 46mJetBlue
Wed 14/508:00SJU - ORD
1 stop11h 36mJetBlue
Deal found 11/4$559
Sat 26/412:40ORD - SJU
2 stops10h 15mSouthwest
Sat 3/506:20SJU - ORD
1 stop7h 25mSouthwest
Deal found 11/4$691

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 11 April 2025. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Auckland

Route

Departure

Return

Price

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 8/5

07:35-09:42

Nonstop4h 07m

Phoenix Sky Harbor Intl

Mon 12/5

10:40-16:13

Nonstop3h 33m

$309

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 8/5

21:02-08:13

1 stop13h 11m

Phoenix Sky Harbor Intl

Mon 12/5

10:40-16:13

Nonstop3h 33m

$319

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 6/5

16:05-18:07

Nonstop4h 02m

Phoenix Sky Harbor Intl

Tue 13/5

14:35-20:05

Nonstop3h 30m

$326

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 3/5

12:00-18:47

1 stop8h 47m

Phoenix Sky Harbor Intl

Tue 6/5

09:00-18:20

1 stop7h 20m

$376

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 8/5

21:02-08:13

1 stop13h 11m

Phoenix Sky Harbor Intl

Mon 12/5

09:19-06:42

2 stops19h 23m

$390

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 10/5

15:33-20:08

1 stop6h 35m

Phoenix Sky Harbor Intl

Fri 16/5

00:45-08:34

1 stop5h 49m

$409

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 14/5

14:50-16:40

Nonstop3h 50m

Phoenix Sky Harbor Intl

Mon 19/5

05:20-16:25

1 stop9h 05m

$438

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 25/8

06:00-13:29

1 stop6h 29m

San Juan Luis Munoz Marin Intl

Sat 6/9

07:00-17:39

1 stop11h 39m

$529

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 13/9

12:45-23:57

1 stop10h 12m

San Juan Luis Munoz Marin Intl

Sat 20/9

01:05-07:31

1 stop7h 26m

$552

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 7/5

16:03-01:49

1 stop8h 46m

San Juan Luis Munoz Marin Intl

Wed 14/5

08:00-18:36

1 stop11h 36m

$559

Flights are sorted by cheapest return flights first.

Deals found on 11/4

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.

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 $376). Flying from Chicago in September will prove the most costly (average of $2,110). 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 (1,593 flights per day), Detroit (1,208 flights per day), and Los Angeles (661 flights per day).

Miami

Miami

From $182

Toronto

Toronto

From $302

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

Los Angeles

Los Angeles

From $211

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Mexico City Benito Juarez, with prices starting at $227. Explore other affordable destinations below.

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

Las Vegas Harry Reid Intl

Las Vegas Harry Reid Intl

From $155

Miami

Miami

From $182

Philadelphia

Philadelphia

From $188

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.
Fiji Airways
8.0
Very Good
180 reviews
Check prices

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.5

Food

7.5

Comfort

8.0

Reviews

1 / 15
6.0
Good

Anonymous,Dec 2024

NAN - LAX

Asked for water before dinner was served, didn’t get it. Dinner served but no drinks was asked or served with dinner. When asked if I wanted my seat made for bedtime, asked for water again. This time I got it. Filled the breakfast form but was still asked what I wanted. Comparing this experience with Fiji air flight from LA to Melbourne. Worse was missing my flight connection to Baltimore since Fiji air opted to wait for a passenger that couldn’t pass security. Instead of leaving at 9:40 pm, we left at 11. So spent overnight at a hotel for next day’s flight. Another expense!
Fiji Airways
8.0
Very Good
180 reviews
Fiji Airways
8.0
Very Good
180 reviews
Check prices

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.5

Food

7.5

Comfort

8.0

Reviews

1 / 15
6.0
Good

Anonymous,Dec 2024

NAN - LAX

Asked for water before dinner was served, didn’t get it. Dinner served but no drinks was asked or served with dinner. When asked if I wanted my seat made for bedtime, asked for water again. This time I got it. Filled the breakfast form but was still asked what I wanted. Comparing this experience with Fiji air flight from LA to Melbourne. Worse was missing my flight connection to Baltimore since Fiji air opted to wait for a passenger that couldn’t pass security. Instead of leaving at 9:40 pm, we left at 11. So spent overnight at a hotel for next day’s flight. Another expense!
Air New Zealand
8.0
Very Good
463 reviews
Fiji Airways
8.0
Very Good
180 reviews
Check prices

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.5

Food

7.5

Comfort

8.0

Reviews

1 / 15
6.0
Good

Anonymous,Dec 2024

NAN - LAX

Asked for water before dinner was served, didn’t get it. Dinner served but no drinks was asked or served with dinner. When asked if I wanted my seat made for bedtime, asked for water again. This time I got it. Filled the breakfast form but was still asked what I wanted. Comparing this experience with Fiji air flight from LA to Melbourne. Worse was missing my flight connection to Baltimore since Fiji air opted to wait for a passenger that couldn’t pass security. Instead of leaving at 9:40 pm, we left at 11. So spent overnight at a hotel for next day’s flight. Another expense!
Cathay Pacific
7.5
Good
844 reviews
Fiji Airways
8.0
Very Good
180 reviews
Check prices

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.5

Food

7.5

Comfort

8.0

Reviews

1 / 15
6.0
Good

Anonymous,Dec 2024

NAN - LAX

Asked for water before dinner was served, didn’t get it. Dinner served but no drinks was asked or served with dinner. When asked if I wanted my seat made for bedtime, asked for water again. This time I got it. Filled the breakfast form but was still asked what I wanted. Comparing this experience with Fiji air flight from LA to Melbourne. Worse was missing my flight connection to Baltimore since Fiji air opted to wait for a passenger that couldn’t pass security. Instead of leaving at 9:40 pm, we left at 11. So spent overnight at a hotel for next day’s flight. Another expense!
United Airlines
7.4
Good
8,644 reviews
Fiji Airways
8.0
Very Good
180 reviews
Check prices

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.5

Food

7.5

Comfort

8.0

Reviews

1 / 15
6.0
Good

Anonymous,Dec 2024

NAN - LAX

Asked for water before dinner was served, didn’t get it. Dinner served but no drinks was asked or served with dinner. When asked if I wanted my seat made for bedtime, asked for water again. This time I got it. Filled the breakfast form but was still asked what I wanted. Comparing this experience with Fiji air flight from LA to Melbourne. Worse was missing my flight connection to Baltimore since Fiji air opted to wait for a passenger that couldn’t pass security. Instead of leaving at 9:40 pm, we left at 11. So spent overnight at a hotel for next day’s flight. Another expense!
Air Canada
7.0
Good
9,096 reviews
Fiji Airways
8.0
Very Good
180 reviews
Check prices

Overall

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.5

Food

7.5

Comfort

8.0

Reviews

1 / 15
6.0
Good

Anonymous,Dec 2024

NAN - LAX

Asked for water before dinner was served, didn’t get it. Dinner served but no drinks was asked or served with dinner. When asked if I wanted my seat made for bedtime, asked for water again. This time I got it. Filled the breakfast form but was still asked what I wanted. Comparing this experience with Fiji air flight from LA to Melbourne. Worse was missing my flight connection to Baltimore since Fiji air opted to wait for a passenger that couldn’t pass security. Instead of leaving at 9:40 pm, we left at 11. So spent overnight at a hotel for next day’s flight. Another expense!

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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 11 April 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, Mumbai.

  • What is the cheapest month to fly from Chicago?

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

  • 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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