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$107+ 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 29/9. 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 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Good one-way deal

$280 or less
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.

Fri 31/1017:50ORD - MIA
1 stop5h 44mMultiple Airlines
Fri 7/1110:15MIA - ORD
Nonstop3h 15mMultiple Airlines
Deal found 16/9$205
Thu 2/1010:27ORD - MIA
Nonstop3h 12mSpirit Airlines
Sun 5/1007:00MIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 13/9$215
Fri 31/1017:50ORD - MIA
1 stop5h 44mFrontier
Fri 7/1105:01MIA - ORD
1 stop6h 40mFrontier
Deal found 16/9$240
Mon 3/1110:27ORD - MIA
Nonstop3h 02mSpirit Airlines
Tue 4/1119:23MIA - ORD
1 stop24h 53mSpirit Airlines
Deal found 15/9$257
Wed 29/1010:35ORD - MIA
Nonstop3h 15mUnited Airlines
Sun 2/1107:00MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 14/9$263
Mon 3/1116:40ORD - MIA
Nonstop3h 10mAmerican Airlines
Tue 4/1106:35MIA - ORD
Nonstop3h 30mAmerican Airlines
Deal found 15/9$265
Fri 26/910:27ORD - MIA
Nonstop3h 12mSpirit Airlines
Mon 29/907:00MIA - ORD
Nonstop3h 18mSpirit Airlines
Deal found 14/9$273
Thu 13/1107:35ORD - MIA
Nonstop3h 14mUnited Airlines
Tue 18/1107:00MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 15/9$285
Tue 7/1010:54ORD - MIA
Nonstop3h 17mUnited Airlines
Sat 11/1012:27MIA - ORD
Nonstop3h 28mUnited Airlines
Deal found 15/9$297
Tue 2/1207:35ORD - MIA
Nonstop3h 14mUnited Airlines
Wed 10/1216:16MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 15/9$298
Sun 15/218:05ORD - MIA
Nonstop3h 16mUnited Airlines
Fri 20/209:00MIA - ORD
Nonstop3h 38mUnited Airlines
Deal found 15/9$300
Fri 31/1013:00ORD - PHX
Nonstop3h 58mUnited Airlines
Wed 5/1113:55PHX - ORD
Nonstop3h 33mUnited Airlines
Deal found 16/9$317

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 16 September 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 18/10

10:54-15:11

Nonstop3h 17m

Miami

Tue 21/10

16:56-22:37

1 stop6h 41m

$330

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 8/11

13:00-15:58

Nonstop3h 58m

Phoenix Sky Harbor Intl

Tue 11/11

15:30-19:59

Nonstop3h 29m

$334

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Thu 9/10

07:30-11:47

Nonstop3h 17m

Miami

Thu 9/10

16:17-18:47

Nonstop3h 30m

$362

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 2/2

07:10-15:47

1 stop7h 37m

Miami

Tue 10/2

16:40-23:54

1 stop8h 14m

$364

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 21/1

09:30-17:24

1 stop6h 54m

Miami

Wed 28/1

18:30-23:54

1 stop6h 24m

$364

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 8/10

10:30-16:30

1 stop5h 00m

Miami

Wed 15/10

10:40-16:41

1 stop7h 01m

$364

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 6/1

05:50-14:20

1 stop7h 30m

Miami

Sat 17/1

19:35-23:54

1 stop5h 19m

$364

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 3/2

14:00-00:06

1 stop11h 06m

Phoenix Sky Harbor Intl

Sat 14/2

19:00-13:04

1 stop17h 04m

$366

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 21/10

13:26-21:59

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Sat 25/10

07:15-17:00

1 stop10h 45m

$381

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 30/12

16:25-23:00

1 stop5h 35m

Miami

Thu 1/1

07:40-12:15

1 stop5h 35m

$397

Flights are sorted by cheapest return flights first.

Deals found on 14/9

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, January is the cheapest month in which you can book a flight from Chicago (average of $718). Flying from Chicago in September will prove the most costly (average of $2,022). 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 (1,680 flights per day), Detroit (1,254 flights per day), and Los Angeles (781 flights per day).

Dallas/Fort Worth
Dallas/Fort Worth
From $113
Miami
Miami
From $182
Mexico City Benito Juarez
Mexico City Benito Juarez
From $131
San Francisco
San Francisco
From $906

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Dallas/Fort Worth, with prices starting at $190. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From $113
Mexico City Benito Juarez
Mexico City Benito Juarez
From $131
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.
Read through reviews of airlines serving Chicago, such as Air Canada. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Overall

7.1

Crew

7.8

Comfort

7.1

Food

6.3

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

TPA - YYZ

The pre boarding was a bit confusing but we got through it.
Air Canada
7.1
Good
10,000 reviews
Air Canada
7.1
Good
10,000 reviews
Check prices

Entertainment

6.8

Overall

7.1

Crew

7.8

Comfort

7.1

Food

6.3

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

TPA - YYZ

The pre boarding was a bit confusing but we got through it.

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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 16 September 2025.

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

    The most popular destinations from Chicago this month are Athens, Boston, Atlanta. The top year-round destinations include Atlanta, Boston, Ahmedabad.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently January; with September 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 $1,469 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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