$81+ 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 25/1. 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
21 ene. — 28 ene.1
1 adult
1 adult, Economy, 0 bags

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 22 diciembre 2025.

Good one-way deal

$90 or less
Price to beat on a one-way flight from Chicago.
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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 22 diciembre 2025.

jue. 22/118:57ORD - MIA
Nonstop3h 17mSpirit Airlines
dom. 25/105:54MIA - ORD
Nonstop3h 24mSpirit Airlines
Deal found 22/12$187
sáb. 2/518:34ORD - MIA
Nonstop3h 17mSpirit Airlines
lun. 4/515:47MIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 22/12$230
mié. 21/110:35ORD - MIA
Nonstop3h 30mUnited Airlines
mié. 21/116:19MIA - ORD
Nonstop3h 36mUnited Airlines
Deal found 21/12$263
lun. 26/110:35ORD - MIA
Nonstop3h 30mUnited Airlines
sáb. 31/109:00MIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 21/12$271
mié. 7/118:05ORD - MIA
Nonstop3h 16mSpirit Airlines
dom. 11/105:54MIA - ORD
Nonstop3h 24mSpirit Airlines
Deal found 21/12$282
mar. 13/116:25ORD - PHX
Nonstop4h 00mSouthwest
sáb. 17/109:05PHX - ORD
Nonstop3h 25mSouthwest
Deal found 21/12$299
mar. 20/107:30ORD - MIA
Nonstop3h 25mUnited Airlines
mar. 27/116:19MIA - ORD
Nonstop3h 36mUnited Airlines
Deal found 22/12$306
sáb. 24/119:56ORD - PHX
Nonstop4h 03mUnited Airlines
sáb. 31/115:50PHX - ORD
Nonstop3h 34mUnited Airlines
Deal found 22/12$306
mié. 28/116:20ORD - PHX
Nonstop4h 02mUnited Airlines
sáb. 31/108:10PHX - ORD
Nonstop3h 34mUnited Airlines
Deal found 21/12$323
jue. 16/407:41ORD - MIA
1 stop12h 09mSpirit Airlines
lun. 20/415:47MIA - ORD
Nonstop3h 28mSpirit Airlines
Deal found 22/12$339
sáb. 21/206:04ORD - SJU
1 stop8h 52mJetBlue
mié. 25/205:10SJU - ORD
1 stop8h 38mJetBlue
Deal found 22/12$339
dom. 11/107:30ORD - MIA
Nonstop3h 25mUnited Airlines
mar. 13/109:00MIA - ORD
Nonstop3h 34mUnited Airlines
Deal found 21/12$341

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 22 diciembre 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

mar. 13/1

16:25-19:25

Nonstop4h 00m

Phoenix Sky Harbor Intl

sáb. 17/1

09:05-13:30

Nonstop3h 25m

$299

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

mar. 27/1

12:55-15:57

Nonstop4h 02m

Phoenix Sky Harbor Intl

sáb. 31/1

12:28-17:00

Nonstop3h 32m

$323

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 21/1

07:45-18:05

1 stop8h 20m

San Juan Luis Munoz Marin Intl

mar. 3/2

11:06-19:36

1 stop10h 30m

$339

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

jue. 22/1

15:44-23:22

1 stop8h 38m

Phoenix Sky Harbor Intl

mar. 27/1

08:24-23:37

1 stop14h 13m

$341

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

jue. 9/4

10:00-22:01

1 stop11h 01m

San Juan Luis Munoz Marin Intl

jue. 16/4

14:40-22:59

1 stop9h 19m

$349

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 20/1

07:45-18:07

1 stop8h 22m

San Juan Luis Munoz Marin Intl

mar. 3/2

11:06-19:36

1 stop10h 30m

$354

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 19/1

10:15-19:26

1 stop7h 11m

San Juan Luis Munoz Marin Intl

mar. 3/2

11:06-19:36

1 stop10h 30m

$354

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 25/2

12:41-22:25

1 stop7h 44m

San Juan Luis Munoz Marin Intl

dom. 1/3

05:10-11:48

1 stop8h 38m

$354

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

jue. 29/1

15:44-23:22

1 stop8h 38m

Phoenix Sky Harbor Intl

dom. 1/2

08:24-23:37

1 stop14h 13m

$356

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

sáb. 17/1

13:00-22:20

1 stop8h 20m

Miami

jue. 29/1

09:00-11:34

Nonstop3h 34m

$361

Flights are sorted by cheapest return flights first.

Deals found on 22/12

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 $1,181). Flying from Chicago in September will prove the most costly (average of $2,308). 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: Orlando (902 flights per day), New York (849 flights per day), and Detroit (798 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $659
San Francisco
San Francisco
From $1,565
Houston Hobby
Houston Hobby
From $65

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Houston Hobby, with prices starting at $65. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $65
Kastrup Copenhagen
Kastrup Copenhagen
From $659
San Francisco
San Francisco
From $1,565

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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 22 diciembre 2025.

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

    The most popular destinations from Chicago this month are Ahmedabad, Mumbai, 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 $1,447 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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