$77+ 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 31/1. 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
15 Feb — 22 Feb1
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 16 January 2026.

Good one-way deal

$91 or less
Price to beat on a one-way flight from Chicago.
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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 16 January 2026.

Mon 2/309:18
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Thu 5/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 13/1$160
Wed 4/209:23
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Wed 11/205:54
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 15/1$169
Mon 27/418:34
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Thu 30/415:47
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 13/1$192
Fri 20/209:18
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Fri 20/215:50
MIA
-
ORD
Nonstop3h 28m
Spirit Airlines
Deal found 15/1$247
Thu 26/208:59
ORD
-
MIA
1 stop10h 52m
Spirit Airlines
Sun 1/307:12
MIA
-
ORD
Nonstop3h 27m
Spirit Airlines
Deal found 14/1$258
Wed 18/210:35
ORD
-
MIA
Nonstop3h 23m
United Airlines
Wed 18/216:10
MIA
-
ORD
Nonstop3h 45m
United Airlines
Deal found 15/1$265
Sat 7/318:08
ORD
-
MIA
Nonstop3h 16m
United Airlines
Wed 11/316:10
MIA
-
ORD
Nonstop3h 44m
United Airlines
Deal found 14/1$273
Wed 4/209:23
ORD
-
MIA
Nonstop3h 18m
Spirit Airlines
Sun 8/205:54
MIA
-
ORD
Nonstop3h 24m
Spirit Airlines
Deal found 15/1$287
Sun 22/213:10
ORD
-
MIA
Nonstop3h 19m
United Airlines
Fri 27/209:00
MIA
-
ORD
Nonstop3h 38m
United Airlines
Deal found 14/1$308
Sat 14/219:55
ORD
-
PHX
Nonstop4h 08m
United Airlines
Wed 18/207:00
PHX
-
ORD
Nonstop3h 29m
United Airlines
Deal found 15/1$308
Thu 16/418:34
ORD
-
MIA
Nonstop3h 17m
Spirit Airlines
Mon 20/407:35
MIA
-
ORD
1 stop7h 40m
Spirit Airlines
Deal found 15/1$310
Thu 26/212:41
ORD
-
SJU
1 stop9h 48m
JetBlue
Fri 6/315:05
SJU
-
ORD
1 stop9h 51m
JetBlue
Deal found 14/1$333

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 16 January 2026. 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 2/3

08:59-20:51

1 stop10h 52m

Miami

Thu 5/3

21:53-07:54

1 stop11h 01m

$272

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 23/2

13:10-17:29

Nonstop3h 19m

Miami

Fri 27/2

09:00-11:38

Nonstop3h 38m

$308

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Sat 7/3

18:08-22:24

Nonstop3h 16m

Miami

Fri 13/3

09:00-11:38

Nonstop3h 38m

$319

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 26/2

12:41-00:29

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Sat 28/2

05:10-12:04

1 stop8h 54m

$333

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 25/3

12:20-22:51

1 stop9h 31m

San Juan Luis Munoz Marin Intl

Thu 26/3

03:26-11:25

1 stop8h 59m

$343

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 31/1

09:40-19:26

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Tue 3/2

09:25-19:36

1 stop12h 11m

$354

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 18/3

10:56-23:23

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Thu 26/3

03:26-11:25

1 stop8h 59m

$359

ChicagoPhoenix

ORD - PHX

ORDPHX

Chicago O'Hare Intl

Tue 14/4

07:45-09:40

Nonstop3h 55m

Phoenix Sky Harbor Intl

Tue 21/4

11:00-22:55

2 stops9h 55m

$371

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/3

10:00-21:56

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Mon 9/3

04:15-11:49

1 stop8h 34m

$374

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Mon 23/2

14:46-20:44

1 stop4h 58m

Miami

Wed 25/2

06:00-10:14

1 stop5h 14m

$378

Flights are sorted by cheapest return flights first.

Deals found on 14/1

Showing 1-10 of 60 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.

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 $1,210). Flying from Chicago in September will prove the most costly (average of $2,531). 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 (1,531 flights per day), Detroit (968 flights per day), and Toronto (830 flights per day).

Kastrup Copenhagen
Kastrup Copenhagen
From $663
San Francisco
San Francisco
From $1,577
Houston Hobby
Houston Hobby
From $66

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 $66. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From $66
Kastrup Copenhagen
Kastrup Copenhagen
From $663
San Francisco
San Francisco
From $1,577

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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 16 January 2026.

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

    The most popular destinations from Chicago this month are Ahmedabad, Atlanta, 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 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.

  • 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 $1,480 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!

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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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