$148+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

Good round-trip deal	$501 or less
Good one-way deal	$277 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 14 June 2025.

Thu 30/1007:35ORD - MIA

Nonstop3h 14mUnited Airlines

Mon 3/1107:00MIA - ORD

Nonstop3h 29mUnited Airlines

Deal found 14/6$228

Tue 8/713:43ORD - MIA

Nonstop3h 17mSpirit Airlines

Wed 9/714:23MIA - ORD

1 stop6h 37mSpirit Airlines

Deal found 14/6$241

Thu 11/906:00ORD - MIA

1 stop4h 50mSouthwest

Mon 15/906:05MIA - ORD

1 stop7h 40mSouthwest

Deal found 13/6$261

Tue 12/807:30ORD - PHX

Nonstop3h 50mUnited Airlines

Fri 15/812:35PHX - ORD

Nonstop3h 41mUnited Airlines

Deal found 13/6$346

Mon 21/709:00ORD - MIA

1 stop7h 10mDelta

Sat 26/708:11MIA - ORD

1 stop5h 39mDelta

Deal found 13/6$360

Wed 3/914:07ORD - PHX

1 stop8h 13mHawaiian Airlines

Tue 9/913:54PHX - ORD

1 stop8h 05mHawaiian Airlines

Deal found 13/6$362

Wed 8/1019:59ORD - PHX

1 stop15h 45mAlaska Airlines

Mon 13/1016:17PHX - ORD

1 stop20h 33mAlaska Airlines

Deal found 13/6$377

Thu 7/816:20ORD - PHX

1 stop7h 40mSouthwest

Tue 12/816:50PHX - ORD

Nonstop3h 30mSouthwest

Deal found 11/6$379

Mon 14/718:21ORD - PHX

1 stop17h 47mSun Country Air

Sun 20/723:57PHX - ORD

1 stop15h 30mSun Country Air

Deal found 13/6$390

Fri 29/818:25ORD - PHX

1 stop6h 11mDelta

Mon 1/913:20PHX - ORD

1 stop5h 40mDelta

Deal found 13/6$394

Mon 28/705:20ORD - PHX

1 stop7h 54mFrontier

Mon 4/817:11PHX - ORD

Nonstop3h 44mFrontier

Deal found 13/6$404

Tue 25/1120:34ORD - MIA

1 stop13h 17mSun Country Air

Thu 27/1112:45MIA - ORD

1 stop22h 18mSun Country Air

Deal found 13/6$440

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 14 June 2025.

Thu 30/1007:35ORD - MIA

Nonstop3h 14mUnited Airlines

Mon 3/1107:00MIA - ORD

Nonstop3h 29mUnited Airlines

Deal found 14/6$228

Tue 8/713:43ORD - MIA

Nonstop3h 17mSpirit Airlines

Wed 9/714:23MIA - ORD

1 stop6h 37mSpirit Airlines

Deal found 14/6$241

Thu 11/906:00ORD - MIA

1 stop4h 50mSouthwest

Mon 15/906:05MIA - ORD

1 stop7h 40mSouthwest

Deal found 13/6$261

Mon 21/709:00ORD - MIA

1 stop7h 10mDelta

Sat 26/708:11MIA - ORD

1 stop5h 39mDelta

Deal found 13/6$360

Wed 3/914:07ORD - PHX

1 stop8h 13mHawaiian Airlines

Tue 9/913:54PHX - ORD

1 stop8h 05mHawaiian Airlines

Deal found 13/6$362

Wed 8/1019:59ORD - PHX

1 stop15h 45mAlaska Airlines

Mon 13/1016:17PHX - ORD

1 stop20h 33mAlaska Airlines

Deal found 13/6$377

Mon 14/718:21ORD - PHX

1 stop17h 47mSun Country Air

Sun 20/723:57PHX - ORD

1 stop15h 30mSun Country Air

Deal found 13/6$390

Mon 28/705:20ORD - PHX

1 stop7h 54mFrontier

Mon 4/817:11PHX - ORD

Nonstop3h 44mFrontier

Deal found 13/6$404

Sat 26/716:49ORD - MIA

Nonstop3h 13mAmerican Airlines

Sat 2/820:11MIA - ORD

Nonstop3h 33mAmerican Airlines

Deal found 13/6$513

Tue 12/807:30ORD - PHX

Nonstop3h 50mUnited Airlines

Fri 15/812:35PHX - ORD

Nonstop3h 41mUnited Airlines

Deal found 13/6$346

Thu 7/816:20ORD - PHX

1 stop7h 40mSouthwest

Tue 12/816:50PHX - ORD

Nonstop3h 30mSouthwest

Deal found 11/6$379

Fri 29/818:25ORD - PHX

1 stop6h 11mDelta

Mon 1/913:20PHX - ORD

1 stop5h 40mDelta

Deal found 13/6$394

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 14 June 2025.

Thu 30/1007:35ORD - MIA

Nonstop3h 14mUnited Airlines

Mon 3/1107:00MIA - ORD

Nonstop3h 29mUnited Airlines

Deal found 14/6$228

Wed 22/1015:11ORD - MIA

Nonstop3h 15mSpirit Airlines

Mon 27/1020:21MIA - ORD

Nonstop3h 26mSpirit Airlines

Deal found 12/6$287

Tue 12/807:30ORD - PHX

Nonstop3h 50mUnited Airlines

Fri 15/812:35PHX - ORD

Nonstop3h 41mUnited Airlines

Deal found 13/6$346

Sun 13/714:50ORD - PHX

Nonstop3h 50mSouthwest

Fri 18/716:50PHX - ORD

Nonstop3h 30mSouthwest

Deal found 13/6$390

Sat 26/716:49ORD - MIA

Nonstop3h 13mAmerican Airlines

Sat 2/820:11MIA - ORD

Nonstop3h 33mAmerican Airlines

Deal found 13/6$513

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 14 June 2025 and is based on user searches.

Fri 20/613:43ORD - MIA

Nonstop3h 17mSpirit Airlines

Wed 25/619:20MIA - ORD

Nonstop3h 36mSpirit Airlines

Deal found 13/6$337

Fri 20/618:17ORD - MIA

1 stop15h 53mSun Country Air

Sun 22/614:08MIA - ORD

1 stop28h 13mSun Country Air

Deal found 12/6$922

Sat 21/607:10ORD - MIA

1 stop4h 58mDelta

Wed 2/708:11MIA - ORD

1 stop5h 44mDelta

Deal found 13/6$532

Sat 21/609:25ORD - PHX

Nonstop3h 54mUnited Airlines

Thu 26/623:09PHX - ORD

Nonstop3h 33mUnited Airlines

Deal found 11/6$643

Sat 21/614:03ORD - PHX

1 stop8h 12mAlaska Airlines

Mon 23/611:52PHX - ORD

2 stops9h 47mAlaska Airlines

Deal found 14/6$1,279

Mon 23/614:50ORD - PHX

Nonstop3h 50mSouthwest

Sat 28/607:40PHX - ORD

Nonstop3h 25mSouthwest

Deal found 12/6$556

Mon 23/610:54ORD - MIA

Nonstop3h 20mUnited Airlines

Thu 26/612:20MIA - ORD

Nonstop3h 35mUnited Airlines

Deal found 12/6$620

Mon 23/608:00ORD - MIA

1 stop6h 27mAmerican Airlines

Thu 26/621:20MIA - ORD

Nonstop3h 31mAmerican Airlines

Deal found 12/6$641

Mon 23/606:00ORD - MIA

2 stops9h 20mSouthwest

Thu 26/607:00MIA - ORD

1 stop10h 25mSouthwest

Deal found 12/6$728

Mon 23/620:20ORD - PHX

Nonstop3h 59mAmerican Airlines

Mon 23/600:30PHX - ORD

Nonstop3h 33mAmerican Airlines

Deal found 12/6$817

Mon 23/620:42ORD - MIA

1 stop19h 38mAlaska Airlines

Mon 30/618:20MIA - ORD

2 stops19h 47mAlaska Airlines

Deal found 12/6$1,751

Tue 24/607:10ORD - PHX

1 stop7h 25mDelta

Sat 28/606:00PHX - ORD

1 stop5h 41mDelta

Deal found 12/6$631

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 14 June 2025.

Sat 19/707:01ORD - MIA

Nonstop3h 17mUnited Airlines

Deal found 12/6$148

Tue 16/906:00ORD - MIA

2 stops9h 40mSouthwest

Deal found 13/6$156

Sat 26/714:00ORD - MIA

1 stop7h 45mDelta

Deal found 13/6$181

Tue 12/807:00ORD - PHX

1 stop8h 16mHawaiian Airlines

Deal found 13/6$181

Fri 21/1117:21ORD - PHX

1 stop7h 31mSun Country Air

Deal found 13/6$188

Sat 30/807:00ORD - PHX

1 stop12h 15mAlaska Airlines

Deal found 12/6$191

Fri 5/906:10ORD - PHX

1 stop8h 26mDelta

Deal found 13/6$198

Tue 8/713:34ORD - PHX

Nonstop3h 48mUnited Airlines

Deal found 11/6$216

Fri 8/807:30ORD - PHX

2 stops10h 10mSouthwest

Deal found 14/6$223

Tue 25/1120:34ORD - MIA

1 stop13h 17mSun Country Air

Deal found 13/6$229

Thu 10/708:40ORD - MIA

1 stop10h 04mJetBlue

Deal found 12/6$309

Mon 23/608:00ORD - MIA

1 stop6h 27mAmerican Airlines

Deal found 12/6$344

Find flights from Chicago within your budget

Fly to

Route

Departure

Return

Price

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 30/7

10:50-15:10

Nonstop3h 20m

Miami

Tue 5/8

17:44-23:41

1 stop6h 57m

$344

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 12/8

07:30-09:20

Nonstop3h 50m

Phoenix Sky Harbor Intl

Fri 15/8

12:35-18:16

Nonstop3h 41m

$346

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sun 27/7

08:09-12:23

Nonstop3h 14m

Miami

Sun 3/8

21:09-07:50

1 stop11h 41m

$347

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Fri 5/9

13:50-21:45

1 stop6h 55m

Miami

Sun 7/9

07:15-11:50

1 stop5h 35m

$354

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 21/7

09:00-17:10

1 stop7h 10m

Miami

Sat 26/7

08:11-12:50

1 stop5h 39m

$360

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 3/9

14:07-20:20

1 stop8h 13m

Phoenix Sky Harbor Intl

Tue 9/9

13:54-23:59

1 stop8h 05m

$362

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Wed 8/10

19:59-09:44

1 stop15h 45m

Phoenix Sky Harbor Intl

Mon 13/10

16:17-14:50

1 stop20h 33m

$377

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Thu 7/8

16:20-22:00

1 stop7h 40m

Phoenix Sky Harbor Intl

Tue 12/8

16:50-22:20

Nonstop3h 30m

$379

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Mon 14/7

18:21-10:08

1 stop17h 47m

Phoenix Sky Harbor Intl

Sun 20/7

23:57-17:27

1 stop15h 30m

$390

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Fri 29/8

18:25-22:36

1 stop6h 11m

Phoenix Sky Harbor Intl

Mon 1/9

13:20-21:00

1 stop5h 40m

$394

Flights are sorted by cheapest return flights first.

Deals found on 12/6

Showing 1-10 of 60 results

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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 $734). Flying from Chicago in September will prove the most costly (average of $2,023). 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 (1,226 flights per day), New York (985 flights per day), and Los Angeles (762 flights per day).

Los Angeles

Miami

Toronto

Mexico City Benito Juarez

Mexico City Benito Juarez

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 $218. Explore other affordable destinations below.

Mexico City Benito Juarez

Mexico City Benito Juarez

Miami

Philadelphia

Minneapolis St Paul

Minneapolis St Paul

Airline reviews for flights from Chicago

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.4

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.1

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.0

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

8.0

Very Good

8.4

Very Good

Reviews

1 / 20

10.0

Excellent

Dale,May 2025

TPE - SFO

Flight staff were very courteous and efficient. Aircraft (seats, lavatories, etc) kept clean and replenished. Food service was timed perfectly and was delicious and had right amount

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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 Athens, Boston, Amman. 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

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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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