$86+ 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 18/5. 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
13 May — 20 May1
1 adult
1 adult, Economy, 0 bags

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 13 April 2026. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Route

Departure

Return

Price

Cheapest return flight
Fastest return journey

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 26/5

07:00-11:24

Nonstop3h 24m

Miami

Thu 28/5

16:06-18:49

Nonstop3h 43m

$286

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/5

05:00-14:23

1 stop8h 23m

Miami

Wed 13/5

12:10-14:50

Nonstop3h 40m

$320

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 1/6

07:07-12:56

1 stop4h 49m

Miami

Sat 6/6

06:33-14:57

1 stop9h 24m

$372

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/6

15:47-23:11

1 stop6h 24m

Miami

Sat 6/6

06:33-14:57

1 stop9h 24m

$372

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 23/5

18:05-22:27

Nonstop3h 22m

Miami

Sat 30/5

07:07-14:46

1 stop8h 39m

$396

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/6

14:59-22:17

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Sat 6/6

07:30-18:41

1 stop12h 11m

$404

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 9/5

13:55-22:05

2 stops7h 10m

Miami

Sat 16/5

06:15-15:30

2 stops10h 15m

$430

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 23/5

16:15-18:15

Nonstop4h 00m

Phoenix Sky Harbor Intl

Tue 26/5

18:30-23:55

Nonstop3h 25m

$437

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 6/5

07:20-09:23

Nonstop4h 03m

Phoenix Sky Harbor Intl

Wed 13/5

23:30-05:01

Nonstop3h 31m

$437

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 28/4

08:49-14:44

Nonstop4h 55m

San Juan Luis Munoz Marin Intl

Fri 22/5

07:40-11:53

Nonstop5h 13m

$440

Flights are sorted by cheapest return flights first.

Deals found on 13/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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?

Use this chart to determine the optimal time to book a return flight from Chicago to Auckland. Price data was last updated on 10 April 2026.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 15 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 $872). Flying from Chicago in September will prove the most costly (average of $2,379). 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: Detroit (1,038 flights per day), New York (928 flights per day), and Los Angeles (662 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $653
Madrid Barajas
Madrid Barajas
From $926
New York
New York
From $170

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 $64. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $64
New York
New York
From $170
Kastrup Copenhagen
Kastrup Copenhagen
From $653

Browse thousands of different options on Cheapflights for your next trip

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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 13 April 2026.

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

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

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently November; 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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