Find flights
Airlines

$130+ 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 12/10. 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
11 Jul — 18 Jul1
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 6 July 2025.

Good round-trip deal

$498 or less

Good one-way deal

$275 or less
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

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 6 July 2025.

Mon 25/810:27ORD - MIA
Nonstop3h 22mSpirit Airlines
Sat 30/807:00MIA - ORD
Nonstop3h 22mSpirit Airlines
Deal found 5/7$228
Wed 30/707:01ORD - MIA
Nonstop3h 17mUnited Airlines
Wed 6/812:20MIA - ORD
Nonstop3h 35mUnited Airlines
Deal found 6/7$252
Thu 21/806:00ORD - MIA
1 stop4h 50mSouthwest
Sun 24/807:00MIA - ORD
1 stop7h 05mSouthwest
Deal found 4/7$259
Sat 8/1115:05ORD - PHX
Nonstop3h 55mSouthwest
Tue 11/1109:05PHX - ORD
Nonstop3h 25mSouthwest
Deal found 4/7$328
Thu 7/822:10ORD - PHX
Nonstop3h 39mAmerican Airlines
Wed 20/812:37PHX - ORD
Nonstop3h 40mAmerican Airlines
Deal found 5/7$330
Sat 16/813:30ORD - MIA
1 stop6h 58mDelta
Wed 20/806:00MIA - ORD
1 stop5h 04mDelta
Deal found 3/7$358
Sat 4/1006:00ORD - PHX
1 stop8h 51mAlaska Airlines
Tue 7/1013:51PHX - ORD
1 stop8h 08mAlaska Airlines
Deal found 4/7$360
Thu 31/709:15ORD - PHX
Nonstop3h 54mUnited Airlines
Sun 3/823:09PHX - ORD
Nonstop3h 33mUnited Airlines
Deal found 4/7$361
Mon 18/819:20ORD - PHX
1 stop6h 22mDelta
Mon 25/823:59PHX - ORD
1 stop6h 38mDelta
Deal found 4/7$391
Fri 7/1118:14ORD - PHX
1 stop23h 12mSun Country Air
Sun 9/1100:59PHX - ORD
1 stop8h 46mSun Country Air
Deal found 4/7$462
Tue 22/706:16ORD - SJU
1 stop7h 56mJetBlue
Mon 28/703:05SJU - ORD
1 stop9h 13mJetBlue
Deal found 4/7$506
Sun 26/1014:20ORD - SJU
Nonstop4h 40mUnited Airlines
Wed 29/1007:10SJU - ORD
Nonstop5h 22mUnited Airlines
Deal found 4/7$525

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 6 July 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

Mon 18/8

07:00-15:15

1 stop7h 15m

Miami

Thu 21/8

07:10-11:50

1 stop5h 40m

$272

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 20/8

20:47-10:14

1 stop12h 27m

Miami

Tue 26/8

07:00-09:22

Nonstop3h 22m

$274

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Tue 2/9

10:54-15:10

Nonstop3h 16m

Miami

Tue 9/9

07:45-14:55

1 stop8h 10m

$320

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 8/11

15:05-18:00

Nonstop3h 55m

Phoenix Sky Harbor Intl

Tue 11/11

09:05-13:30

Nonstop3h 25m

$328

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 7/8

22:10-23:49

Nonstop3h 39m

Phoenix Sky Harbor Intl

Wed 20/8

12:37-18:17

Nonstop3h 40m

$330

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 16/8

13:30-21:28

1 stop6h 58m

Miami

Wed 20/8

06:00-10:04

1 stop5h 04m

$358

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Sat 4/10

06:00-12:51

1 stop8h 51m

Phoenix Sky Harbor Intl

Tue 7/10

13:51-23:59

1 stop8h 08m

$360

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 31/7

09:15-11:09

Nonstop3h 54m

Phoenix Sky Harbor Intl

Sun 3/8

23:09-04:42

Nonstop3h 33m

$361

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 18/8

19:20-23:42

1 stop6h 22m

Phoenix Sky Harbor Intl

Mon 25/8

23:59-08:37

1 stop6h 38m

$391

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 7/11

18:14-16:26

1 stop23h 12m

Phoenix Sky Harbor Intl

Sun 9/11

00:59-10:45

1 stop8h 46m

$462

Flights are sorted by cheapest return flights first.

Deals found on 4/7

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, January is the cheapest month in which you can book a flight from Chicago (average of $732). Flying from Chicago in September will prove the most costly (average of $2,009). 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 (708 flights per day), New York (700 flights per day), and Los Angeles (479 flights per day).

Miami
Miami
From $182
Toronto
Toronto
From $302
Mexico City Benito Juarez
Mexico City Benito Juarez
From $131
Minneapolis St Paul
Minneapolis St Paul
From $293

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 $217. Explore other affordable destinations below.

Mexico City Benito Juarez
Mexico City Benito Juarez
From $131
Miami
Miami
From $182
Philadelphia
Philadelphia
From $188
Minneapolis St Paul
Minneapolis St Paul
From $293

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 Singapore Airlines, Fiji Airways, andAir New Zealand. 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.
Singapore Airlines
8.1
Very Good
1,321 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.7

Overall

8.1

Comfort

7.9

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Singapore Airlines
8.1
Very Good
1,321 reviews
Singapore Airlines
8.1
Very Good
1,321 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.7

Overall

8.1

Comfort

7.9

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Fiji Airways
8.0
Very Good
201 reviews
Singapore Airlines
8.1
Very Good
1,321 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.7

Overall

8.1

Comfort

7.9

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Air New Zealand
8.0
Very Good
488 reviews
Singapore Airlines
8.1
Very Good
1,321 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.7

Overall

8.1

Comfort

7.9

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
Qantas Airways
7.5
Good
873 reviews
Singapore Airlines
8.1
Very Good
1,321 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.7

Overall

8.1

Comfort

7.9

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.
United Airlines
7.4
Good
8,849 reviews
Singapore Airlines
8.1
Very Good
1,321 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.7

Overall

8.1

Comfort

7.9

Entertainment

8.0

Reviews

1 / 20
2.0
Mediocre

Ketan,Nov 2024

SEA - SIN

Sin to amd was not good flight. Food was bad. It was like few days old.

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 Miami
Direct flights from Salt Lake City
Direct flights from San Diego
Direct flights from Atlanta
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 New Orleans
Direct flights from Philadelphia
Direct flights from Charlotte
Direct flights from Austin
Direct flights from Fort Lauderdale
Direct flights from Tampa
Direct flights from Kansas City
Direct flights from Cleveland
Direct flights from Cincinnati
Direct flights from Kahului
Direct flights from Pittsburgh
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 6 July 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, Mumbai.

  • 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.

  • 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.
Site
©2025 Cheapflights