$103+ 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 28/11. 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
2 Dec — 9 Dec1
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 2 November 2025.

Good one-way deal

$665 or less
Price to beat on a one-way flight from Chicago.
Search Deals

Find flights from Chicago

Enter your travel dates to find the best prices.

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 2 November 2025.

Sun 23/1111:40ORD - MIA
Nonstop3h 07mSpirit Airlines
Tue 25/1108:10MIA - ORD
Nonstop3h 25mSpirit Airlines
Deal found 2/11$215
Wed 17/1219:41ORD - MIA
Nonstop3h 16mMultiple Airlines
Wed 24/1205:30MIA - ORD
1 stop14h 03mMultiple Airlines
Deal found 2/11$220
Mon 15/1210:55ORD - MIA
Nonstop3h 15mUnited Airlines
Mon 15/1216:16MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 1/11$265
Thu 4/1212:39ORD - MIA
Nonstop3h 11mUnited Airlines
Thu 11/1212:23MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 1/11$274
Mon 19/113:45ORD - MIA
1 stop5h 35mSouthwest
Fri 23/107:55MIA - ORD
1 stop5h 20mSouthwest
Deal found 2/11$309
Sat 14/213:05ORD - PHX
Nonstop4h 09mUnited Airlines
Tue 17/218:31PHX - ORD
Nonstop3h 28mUnited Airlines
Deal found 31/10$309
Tue 2/1207:35ORD - MIA
Nonstop3h 14mUnited Airlines
Tue 9/1216:16MIA - ORD
Nonstop3h 29mUnited Airlines
Deal found 2/11$311
Wed 4/206:05ORD - MIA
2 stops13h 55mSouthwest
Wed 18/206:55MIA - ORD
1 stop5h 15mSouthwest
Deal found 2/11$318
Sat 14/214:15ORD - PHX
Nonstop4h 05mSouthwest
Tue 17/205:30PHX - ORD
1 stop5h 45mSouthwest
Deal found 31/10$326
Mon 12/116:25ORD - PHX
Nonstop4h 00mSouthwest
Sat 17/109:05PHX - ORD
Nonstop3h 25mSouthwest
Deal found 2/11$330
Wed 10/1216:25ORD - PHX
Nonstop3h 55mSouthwest
Tue 16/1209:05PHX - ORD
Nonstop3h 25mSouthwest
Deal found 2/11$344
Sat 13/1209:25ORD - PHX
Nonstop4h 07mUnited Airlines
Wed 17/1213:45PHX - ORD
Nonstop3h 33mUnited Airlines
Deal found 31/10$346

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 2 November 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

Thu 4/12

12:39-16:50

Nonstop3h 11m

Miami

Thu 11/12

12:23-14:52

Nonstop3h 29m

$274

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 3/12

16:25-19:20

Nonstop3h 55m

Phoenix Sky Harbor Intl

Sun 7/12

09:05-13:30

Nonstop3h 25m

$361

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 14/1

13:45-21:35

2 stops8h 50m

Phoenix Sky Harbor Intl

Sun 18/1

06:00-13:00

1 stop6h 00m

$370

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/2

17:54-00:51

1 stop5h 57m

Miami

Thu 19/2

12:03-16:40

1 stop5h 37m

$379

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 3/12

05:30-11:21

1 stop4h 51m

Miami

Wed 10/12

10:32-15:20

1 stop5h 48m

$379

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 9/2

10:35-17:48

1 stop6h 13m

Miami

Tue 17/2

12:00-16:53

1 stop5h 53m

$379

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 24/1

15:49-10:59

1 stop20h 10m

Phoenix Sky Harbor Intl

Sat 31/1

15:45-23:37

1 stop6h 52m

$381

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 13/12

06:00-14:00

1 stop9h 00m

Phoenix Sky Harbor Intl

Tue 16/12

13:33-22:43

1 stop8h 10m

$381

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 3/12

15:05-23:59

1 stop9h 54m

Phoenix Sky Harbor Intl

Mon 8/12

06:02-14:09

1 stop7h 07m

$395

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 25/1

05:40-16:36

1 stop8h 56m

San Juan Luis Munoz Marin Intl

Wed 28/1

17:50-23:39

1 stop7h 49m

$396

Flights are sorted by cheapest return flights first.

Deals found on 2/11

Showing 1-10 of 60 results
1
2
3
...
6

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, November is the cheapest month in which you can book a flight from Chicago (average of $812). Flying from Chicago in August will prove the most costly (average of $2,086). 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 (711 flights per day), Detroit (432 flights per day), and Toronto (418 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $665
San Francisco
San Francisco
From $1,581

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Kastrup Copenhagen, with prices starting at $665. Explore other affordable destinations below.

Kastrup Copenhagen
Kastrup Copenhagen
From $665
San Francisco
San Francisco
From $1,581

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from Los Angeles
Direct flights from Honolulu
Direct flights from San Francisco
Direct flights from Las Vegas
Direct flights from Orlando
Direct flights from Seattle
Direct flights from Salt Lake City
Direct flights from Miami
Direct flights from Atlanta
Direct flights from San Diego
Direct flights from Boston
Direct flights from Anchorage
Direct flights from Denver
Direct flights from Minneapolis
Direct flights from Portland
Direct flights from Nashville
Direct flights from Indianapolis
Direct flights from Austin
Direct flights from Philadelphia
Direct flights from Charlotte
Direct flights from Fort Lauderdale
Direct flights from New Orleans
Direct flights from Tampa
Direct flights from Cincinnati
Direct flights from Cleveland
Direct flights from Kansas City
Direct flights from Pittsburgh
Direct flights from Kahului
Direct flights from Memphis
Direct flights from San Antonio

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 2 November 2025.

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

    The most popular destinations from Chicago this month are Atlanta, Boston, Mumbai. 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 November; with August 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 $1,624 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!

See more FAQs

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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.