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Orange Beach

$91+ Cheap flights from Chicago (CHI) to Orange Beach, AL

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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Orange Beach are usually found in January or April, booked 16 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Orange Beach

Keep the following information in mind while searching for Chicago to Orange Beach flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$203
(United Airlines)

One-way from

$91
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$304
From Chicago (CHI) to Orange Beach
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One-way flight from Chicago (CHI) to Orange Beach
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Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Orange Beach

Cheapest flights from Chicago to Orange Beach
Explore the most affordable flight options available from Chicago to Orange Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/1410:50 amORD - PNS
Nonstop2h 25mUnited Airlines
vie. 10/172:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Deal found 9/15$203
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/266:50 amORD - PNS
1 stop9h 40mFrontier
lun. 11/35:07 pmPNS - ORD
1 stop7h 08mFrontier
Deal found 9/14$204
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/16:30 amORD - PNS
1 stop11h 40mSpirit Airlines
sáb. 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/16$205
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/58:41 amORD - PNS
1 stop6h 55mSpirit Airlines
dom. 11/94:41 pmPNS - ORD
1 stop7h 01mSpirit Airlines
Deal found 9/14$206
This Priceline deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/78:41 amORD - PNS
1 stop6h 55mSpirit Airlines
dom. 11/94:41 pmPNS - ORD
1 stop7h 01mSpirit Airlines
Deal found 9/15$209
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/316:00 amORD - PNS
1 stop9h 35mFrontier
vie. 11/74:30 pmPNS - ORD
1 stop7h 45mFrontier
Deal found 9/14$210
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/125:05 amORD - PNS
1 stop10h 26mSpirit Airlines
dom. 10/194:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/14$211
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/17:15 amORD - PNS
1 stop8h 20mFrontier
sáb. 11/84:30 pmPNS - ORD
1 stop7h 42mFrontier
Deal found 9/14$213
This Expedia deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/306:30 amORD - PNS
1 stop11h 40mSpirit Airlines
sáb. 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/14$214
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/216:45 amORD - PNS
1 stop5h 52mDelta
mié. 10/296:00 amPNS - ORD
1 stop4h 20mDelta
Deal found 9/16$217
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/88:40 amMDW - PNS
1 stop6h 45mSouthwest
mar. 10/1410:10 amPNS - MDW
1 stop5h 45mSouthwest
Deal found 9/14$217
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/1910:50 amMDW - PNS
1 stop4h 45mSouthwest
mié. 11/269:50 amPNS - MDW
1 stop7h 00mSouthwest
Deal found 9/15$218

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Orange Beach that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from Chicago to Orange Beach that are best for you.

Fly from

Chicago

Fly to

Orange Beach

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 10/21

1:26 pm-7:17 pm

1 stop5h 51m

Pensacola

mié. 10/29

7:00 am-12:16 pm

1 stop5h 16m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mié. 10/8

8:40 am-3:25 pm

1 stop6h 45m

Pensacola

mar. 10/14

10:10 am-3:55 pm

1 stop5h 45m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mié. 10/22

10:50 am-4:40 pm

1 stop5h 50m

Pensacola

mié. 10/29

1:25 pm-7:05 pm

1 stop5h 40m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mar. 12/2

5:35 am-9:20 am

1 stop3h 45m

Pensacola

mié. 12/3

4:15 pm-8:15 pm

1 stop4h 00m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mié. 11/5

5:35 am-9:20 am

1 stop3h 45m

Pensacola

mié. 11/19

4:15 pm-8:15 pm

1 stop4h 00m

$217

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mié. 11/19

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

mié. 11/26

9:50 am-4:50 pm

1 stop7h 00m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 12/2

9:50 am-4:35 pm

1 stop6h 45m

Pensacola

jue. 12/4

5:45 pm-9:53 pm

1 stop4h 08m

$223

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

mar. 10/28

5:20 am-10:42 am

1 stop5h 22m

Pensacola

sáb. 11/8

9:46 am-5:00 pm

1 stop7h 14m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

mar. 12/2

5:32 pm-11:06 pm

1 stop5h 34m

Pensacola

dom. 12/14

6:00 am-9:54 am

1 stop3h 54m

$223

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

dom. 10/26

5:35 am-9:10 am

1 stop3h 35m

Pensacola

mié. 10/29

2:30 pm-6:10 pm

1 stop3h 40m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 39 results
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Best time to book a flight from Chicago to Orange Beach

Have a flexible travel schedule? Discover the best time to fly to Orange Beach from Chicago with our price prediction graph.
Estimated round-trip 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Orange Beach

How far ahead should I book a flight from Chicago to Orange Beach?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Orange Beach. Price data was last updated on September 12, 2025.

The best time to book flights from Chicago to Orange Beach is 16 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Orange Beach?

Currently, September is the cheapest month in which you can book a flight from Chicago to Orange Beach (average of $302). Flying from Chicago to Orange Beach in March is currently the most expensive (average of $415). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to OB9?

Find hourly flight availability from Chicago to Orange Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

When flying from Chicago to Orange Beach, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Orange Beach?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Orange Beach. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Orange Beach flight should consider departing on Wednesday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Orange Beach

Get insights into the airlines that provide service to Orange Beach. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orange Beach. Reviews last updated septiembre 16, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Orange Beach. 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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,019 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Orange Beach. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Orange Beach?

    A quick flight from Chicago to Orange Beach can take about 2h 30m. Delta provides one of the quickest options available for as low as $234. The distance between Chicago and Orange Beach is about 795 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Orange Beach one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $91. Frontier flights start at $99 while deals on United Airlines start at $99 one-way.

  • What are the most reliable airlines from Chicago to Orange Beach?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Orange Beach on time: United Airlines (90%), Air New Zealand (90%), American Airlines (80%).

  • What are the cheapest flights from Chicago to Orange Beach?

    While on average a flight from Chicago to Orange Beach is generally $368, our data shows the cheapest flight currently is $107. When looking at the most popular route, (Chicago O'Hare Intl - Pensacola), you can expect to pay $182 for that flight.

  • Can I find deals for flights from Chicago to Orange Beach that include hotel bookings?

    Yes. In addition to deals on Chicago to Orange Beach flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Orange Beach?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Orange Beach.

  • Can I find deals for business class flights from Chicago to Orange Beach?

    Yes. Cheapflights offers flight deals from Chicago to Orange Beach by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Orange Beach?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Orange Beach (average of $302). Flying from Chicago to Orange Beach in March is currently the most expensive (average of $415). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Orange Beach

Discover the top 6 airlines that operate flights from Chicago to Orange Beach. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$138FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$399FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$387FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$225Average$395FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$416FlexibilityNo cancel feeOn-time69%

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