$178+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

Good round-trip deal	$526 or less
Good one-way deal	$175 or less

Price to beat on a round-trip flight from Chicago.

Price to beat on a one-way flight from Chicago.

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 21 February 2025.

Wed 23/414:20ORD - PHX

1 stop8h 17mDelta

Tue 29/411:00PHX - ORD

1 stop10h 59mDelta

Deal found 21/2$354

Tue 15/407:50ORD - PHX

Nonstop3h 59mUnited Airlines

Mon 21/400:45PHX - ORD

Nonstop3h 27mUnited Airlines

Deal found 20/2$380

Fri 8/820:10ORD - PHX

1 stop23h 04mSun Country Air

Sun 10/818:10PHX - ORD

1 stop23h 01mSun Country Air

Deal found 20/2$462

Mon 31/314:50ORD - PHX

Nonstop3h 55mSouthwest

Wed 9/416:50PHX - ORD

Nonstop3h 30mSouthwest

Deal found 20/2$465

Mon 10/307:35ORD - SJU

1 stop8h 08mDelta

Thu 13/314:13SJU - ORD

1 stop7h 31mDelta

Deal found 20/2$472

Wed 26/317:53ORD - PHX

1 stop8h 19mAlaska Airlines

Wed 2/417:06PHX - ORD

1 stop10h 34mAlaska Airlines

Deal found 20/2$483

Sun 6/416:32ORD - SJU

1 stop15h 54mSpirit Airlines

Sun 13/416:19SJU - ORD

2 stops33h 22mSpirit Airlines

Deal found 20/2$500

Fri 7/311:44ORD - SJU

1 stop10h 06mJetBlue

Wed 12/304:00SJU - ORD

1 stop7h 43mJetBlue

Deal found 20/2$512

Tue 22/418:03ORD - SJU

Nonstop4h 51mUnited Airlines

Tue 29/401:05SJU - ORD

1 stop9h 40mUnited Airlines

Deal found 20/2$568

Mon 31/316:58ORD - PHX

Nonstop3h 57mAmerican Airlines

Thu 3/406:45PHX - ORD

Nonstop3h 29mAmerican Airlines

Deal found 20/2$596

Wed 30/406:00ORD - PHX

1 stop8h 54mHawaiian Airlines

Sat 3/509:00PHX - ORD

1 stop8h 10mHawaiian Airlines

Deal found 20/2$603

Sun 6/409:24ORD - SJU

1 stop23h 02mMultiple Airlines

Sat 12/400:32SJU - ORD

2 stops14h 43mMultiple Airlines

Deal found 20/2$640

Best flights from Chicago
Discover carefully curated flight deals from Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 21 February 2025.

Wed 23/414:20ORD - PHX

1 stop8h 17mDelta

Tue 29/411:00PHX - ORD

1 stop10h 59mDelta

Deal found 21/2$354

Tue 15/407:50ORD - PHX

Nonstop3h 59mUnited Airlines

Mon 21/400:45PHX - ORD

Nonstop3h 27mUnited Airlines

Deal found 20/2$380

Fri 8/820:10ORD - PHX

1 stop23h 04mSun Country Air

Sun 10/818:10PHX - ORD

1 stop23h 01mSun Country Air

Deal found 20/2$462

Mon 31/314:50ORD - PHX

Nonstop3h 55mSouthwest

Wed 9/416:50PHX - ORD

Nonstop3h 30mSouthwest

Deal found 20/2$465

Wed 26/317:53ORD - PHX

1 stop8h 19mAlaska Airlines

Wed 2/417:06PHX - ORD

1 stop10h 34mAlaska Airlines

Deal found 20/2$483

Sun 6/416:32ORD - SJU

1 stop15h 54mSpirit Airlines

Sun 13/416:19SJU - ORD

2 stops33h 22mSpirit Airlines

Deal found 20/2$500

Fri 7/311:44ORD - SJU

1 stop10h 06mJetBlue

Wed 12/304:00SJU - ORD

1 stop7h 43mJetBlue

Deal found 20/2$512

Mon 31/316:58ORD - PHX

Nonstop3h 57mAmerican Airlines

Thu 3/406:45PHX - ORD

Nonstop3h 29mAmerican Airlines

Deal found 20/2$596

Wed 30/406:00ORD - PHX

1 stop8h 54mHawaiian Airlines

Sat 3/509:00PHX - ORD

1 stop8h 10mHawaiian Airlines

Deal found 20/2$603

Sun 6/409:24ORD - SJU

1 stop23h 02mMultiple Airlines

Sat 12/400:32SJU - ORD

2 stops14h 43mMultiple Airlines

Deal found 20/2$640

Mon 10/307:35ORD - SJU

1 stop8h 08mDelta

Thu 13/314:13SJU - ORD

1 stop7h 31mDelta

Deal found 20/2$472

Tue 22/418:03ORD - SJU

Nonstop4h 51mUnited Airlines

Tue 29/401:05SJU - ORD

1 stop9h 40mUnited Airlines

Deal found 20/2$568

Direct flights from Chicago
Explore direct flight options from Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 21 February 2025.

Tue 15/407:50ORD - PHX

Nonstop3h 59mUnited Airlines

Mon 21/400:45PHX - ORD

Nonstop3h 27mUnited Airlines

Deal found 20/2$380

Mon 31/314:50ORD - PHX

Nonstop3h 55mSouthwest

Wed 9/416:50PHX - ORD

Nonstop3h 30mSouthwest

Deal found 20/2$465

Mon 31/316:58ORD - PHX

Nonstop3h 57mAmerican Airlines

Thu 3/406:45PHX - ORD

Nonstop3h 29mAmerican Airlines

Deal found 20/2$596

Tue 11/314:20ORD - SJU

Nonstop4h 35mUnited Airlines

Wed 12/315:52SJU - ORD

Nonstop5h 19mUnited Airlines

Deal found 20/2$648

Sun 6/408:39ORD - SJU

Nonstop4h 36mSpirit Airlines

Sun 13/406:35SJU - ORD

Nonstop5h 23mSpirit Airlines

Deal found 20/2$668

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 21 February 2025 and is based on user searches.

Wed 26/205:45ORD - PHX

1 stop6h 20mSouthwest

Sat 1/305:20PHX - ORD

2 stops10h 25mSouthwest

Deal found 19/2$701

Thu 27/211:44ORD - SJU

1 stop8h 06mJetBlue

Tue 4/305:01SJU - ORD

1 stop7h 58mJetBlue

Deal found 20/2$676

Thu 27/208:50ORD - CHC

2 stops34h 45mQantas Airways

Tue 11/306:00CHC - ORD

2 stops35h 59mQantas Airways

Deal found 20/2$1,696

Fri 28/218:35ORD - SJU

1 stop9h 37mUnited Airlines

Mon 3/302:05SJU - ORD

1 stop9h 00mUnited Airlines

Deal found 20/2$490

Sat 1/314:55ORD - PHX

1 stop8h 00mDelta

Wed 19/306:09PHX - ORD

1 stop8h 06mDelta

Deal found 20/2$553

Sat 1/306:30ORD - SJU

2 stops14h 30mSouthwest

Wed 5/306:00SJU - ORD

1 stop10h 00mSouthwest

Deal found 20/2$570

Sat 1/316:55ORD - WLG

2 stops35h 55mQantas Airways

Sat 15/306:00WLG - ORD

2 stops35h 59mQantas Airways

Deal found 20/2$1,693

Sun 2/307:05ORD - SJU

1 stop7h 51mDelta

Thu 6/307:30SJU - ORD

1 stop8h 19mDelta

Deal found 21/2$472

Sun 2/316:10ORD - PHX

Nonstop4h 06mUnited Airlines

Mon 17/300:45PHX - ORD

Nonstop3h 20mUnited Airlines

Deal found 19/2$554

Sun 2/307:45ORD - PHX

1 stop8h 43mAlaska Airlines

Thu 6/319:35PHX - ORD

1 stop9h 18mAlaska Airlines

Deal found 20/2$638

Mon 3/311:35ORD - AKL

2 stops28h 25mAir Canada

Tue 11/307:00AKL - ORD

3 stops30h 37mAir Canada

Deal found 20/2$1,853

Mon 3/316:55ORD - AKL

2 stops36h 30mMultiple Airlines

Fri 28/314:50AKL - ORD

2 stops33h 09mMultiple Airlines

Deal found 20/2$2,200

One-way flights from Chicago
Search for one-way flight options from Chicago. Find affordable one-way fares based on user searches. Data last updated 21 February 2025.

Tue 22/414:15ORD - PHX

1 stop10h 17mDelta

Deal found 21/2$178

Tue 22/411:05ORD - PHX

Nonstop4h 04mUnited Airlines

Deal found 21/2$190

Tue 22/414:50ORD - PHX

Nonstop3h 50mSouthwest

Deal found 21/2$225

Fri 25/418:03ORD - SJU

Nonstop4h 51mUnited Airlines

Deal found 20/2$228

Sat 1/310:05ORD - SJU

1 stop11h 54mDelta

Deal found 20/2$237

Wed 5/316:05ORD - PHX

1 stop8h 54mAlaska Airlines

Deal found 20/2$258

Thu 26/620:10ORD - PHX

1 stop28h 34mSun Country Air

Deal found 20/2$275

Tue 19/811:35ORD - SJU

1 stop10h 15mJetBlue

Deal found 20/2$282

Sat 1/316:05ORD - PHX

1 stop8h 54mHawaiian Airlines

Deal found 20/2$312

Fri 8/820:10ORD - SJU

1 stop18h 06mSun Country Air

Deal found 20/2$354

Thu 27/211:25ORD - SJU

2 stops11h 35mSouthwest

Deal found 20/2$370

Mon 5/507:35ORD - AKL

2 stops29h 25mMultiple Airlines

Deal found 19/2$910

Find flights from Chicago within your budget

Fly to

Route

Departure

Return

Price

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 23/4

14:20-20:37

1 stop8h 17m

Phoenix Sky Harbor Intl

Tue 29/4

11:00-23:59

1 stop10h 59m

$354

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 15/4

07:50-09:49

Nonstop3h 59m

Phoenix Sky Harbor Intl

Mon 21/4

00:45-06:12

Nonstop3h 27m

$380

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 8/8

20:10-17:14

1 stop23h 04m

Phoenix Sky Harbor Intl

Sun 10/8

18:10-19:11

1 stop23h 01m

$462

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 31/3

14:50-16:45

Nonstop3h 55m

Phoenix Sky Harbor Intl

Wed 9/4

16:50-22:20

Nonstop3h 30m

$465

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 10/3

07:35-16:43

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Thu 13/3

14:13-20:44

1 stop7h 31m

$472

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 26/3

17:53-00:12

1 stop8h 19m

Phoenix Sky Harbor Intl

Wed 2/4

17:06-05:40

1 stop10h 34m

$483

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 6/4

16:32-09:26

1 stop15h 54m

San Juan Luis Munoz Marin Intl

Sun 13/4

16:19-00:41

2 stops33h 22m

$500

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 7/3

11:44-23:50

1 stop10h 06m

San Juan Luis Munoz Marin Intl

Wed 12/3

04:00-10:43

1 stop7h 43m

$512

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 22/4

18:03-23:54

Nonstop4h 51m

San Juan Luis Munoz Marin Intl

Tue 29/4

01:05-09:45

1 stop9h 40m

$568

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 31/3

16:58-18:55

Nonstop3h 57m

Phoenix Sky Harbor Intl

Thu 3/4

06:45-12:14

Nonstop3h 29m

$596

Flights are sorted by cheapest return flights first.

Deals found on 21/2

Showing 1-10 of 51 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.

When is the best time to book a flight from Chicago?

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 22 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, August is the cheapest month in which you can book a flight from Chicago (average of $380). Flying from Chicago in June will prove the most costly (average of $2,174). 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 (1,526 flights per day), Detroit (978 flights per day), and Orlando (795 flights per day).

Miami

Miami

From $182

Toronto

Toronto

From $302

San Francisco

San Francisco

From $100

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is San Francisco, with prices starting at $175. Explore other affordable destinations below.

San Francisco

San Francisco

From $100

Mexico City Benito Juarez

Mexico City Benito Juarez

From $131

Las Vegas Harry Reid Intl

Las Vegas Harry Reid Intl

From $155

Miami

Miami

From $182

Airline reviews for flights from Chicago

Alaska Airlines

8.0

Very Good

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very Good

Alaska Airlines

8.0

Very Good

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

8.0

Very Good

Alaska Airlines

8.0

Very Good

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

8.0

Very Good

Alaska Airlines

8.0

Very Good

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Air New Zealand

7.9

Good

Alaska Airlines

8.0

Very Good

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

7.6

Good

Alaska Airlines

8.0

Very Good

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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Related info for your journey

What are the most popular destinations to fly to from Chicago?
The most popular destinations from Chicago this month are Atlanta, Mumbai, Ahmedabad. The top year-round destinations include Atlanta, Boston, Athens.
What is the cheapest month to fly from Chicago?
At the present moment the cheapest month to fly from Chicago is currently August; with June 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

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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