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Orange Beach

$41+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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The best prices from Chicago to Orange Beach are usually found in January or April, booked 62 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Orange Beach

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Orange Beach (OB9). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(Mytrip)

One-way from

$41
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$299
Provider with most accurate pricing for Chicago (CHI)-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Pensacola flights.
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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. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:00 amORD - PNS
2 stops13h 46mSpirit Airlines
Sat 5/108:46 amPNS - ORD
1 stop11h 54mSpirit Airlines
Deal found 1/29$215
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/712:25 pmORD - PNS
1 stop6h 15mMultiple Airlines
Sun 2/97:17 pmPNS - ORD
1 stop18h 54mMultiple Airlines
Deal found 1/29$216
This Delta deal was found by Cheapflights users on 1/30. 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.
Mon 3/36:00 amMDW - PNS
1 stop3h 57mDelta
Tue 3/117:05 amPNS - MDW
1 stop5h 01mDelta
Deal found 1/30$217
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/226:32 pmORD - PNS
1 stop23h 58mFrontier
Sat 3/15:36 pmPNS - ORD
1 stop19h 49mFrontier
Deal found 1/29$218
This Southwest deal was found by Cheapflights users on 1/29. 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.
Wed 2/196:25 amMDW - PNS
1 stop4h 35mSouthwest
Thu 2/207:40 amPNS - MDW
2 stops6h 20mSouthwest
Deal found 1/29$222
This Frontier deal was found by Cheapflights users on 1/30. 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.
Thu 2/206:40 amMDW - PNS
1 stop11h 47mFrontier
Tue 2/255:23 pmPNS - MDW
1 stop6h 54mFrontier
Deal found 1/30$230
This Delta deal was found by Cheapflights users on 1/29. 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.
Mon 2/175:45 amORD - PNS
1 stop5h 41mDelta
Wed 2/192:48 pmPNS - ORD
1 stop5h 58mDelta
Deal found 1/29$233
This American Airlines deal was found by Cheapflights users on 1/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/121:54 pmORD - PNS
1 stop7h 26mAmerican Airlines
Thu 2/137:01 pmPNS - ORD
1 stop4h 52mAmerican Airlines
Deal found 1/29$249
This Southwest deal was found by Cheapflights users on 1/30. 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.
Tue 3/187:30 amORD - PNS
2 stops13h 10mSouthwest
Sat 3/226:50 amPNS - ORD
1 stop8h 10mSouthwest
Deal found 1/30$258
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Mon 3/102:18 pmORD - PNS
1 stop7h 41mUnited Airlines
Thu 3/132:10 pmPNS - ORD
Nonstop2h 38mUnited Airlines
Deal found 1/30$262

Find flights from Chicago to Orange Beach within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 5/7

6:00 am-7:46 pm

2 stops13h 46m

Pensacola

Sat 5/10

8:46 am-8:40 pm

1 stop11h 54m

$215

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 3/3

6:00 am-9:57 am

1 stop3h 57m

Pensacola

Tue 3/11

7:05 am-12:06 pm

1 stop5h 01m

$217

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 2/22

6:32 pm-6:30 pm

1 stop23h 58m

Pensacola

Sat 3/1

5:36 pm-1:25 pm

1 stop19h 49m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 3/10

6:30 am-6:27 pm

1 stop11h 57m

Pensacola

Sun 3/16

6:49 pm-9:22 am

1 stop14h 33m

$219

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 2/19

6:25 am-11:00 am

1 stop4h 35m

Pensacola

Thu 2/20

7:40 am-2:00 pm

2 stops6h 20m

$222

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 2/20

6:40 am-6:27 pm

1 stop11h 47m

Pensacola

Tue 2/25

5:23 pm-12:17 am

1 stop6h 54m

$230

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 2/17

5:45 am-11:26 am

1 stop5h 41m

Pensacola

Wed 2/19

2:48 pm-8:46 pm

1 stop5h 58m

$233

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 2/12

1:54 pm-9:20 pm

1 stop7h 26m

Pensacola

Thu 2/13

7:01 pm-11:53 pm

1 stop4h 52m

$249

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 3/18

7:30 am-8:40 pm

2 stops13h 10m

Pensacola

Sat 3/22

6:50 am-3:00 pm

1 stop8h 10m

$258

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 2/18

11:07 am-1:31 pm

Nonstop2h 24m

Pensacola

Sat 2/22

3:10 pm-10:58 pm

1 stop7h 48m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 21 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.

Travel insights for flights from Chicago to Orange Beach

Get recent, data-driven insights about flights from Chicago to Orange Beach including ideal travel times, pricing trends, and more.

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 January 24, 2025.

The best time to book flights from Chicago to Orange Beach is 62 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 $306). Flying from Chicago to Orange Beach in March is currently the most expensive (average of $418). 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 January 30, 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. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Orange Beach by month

Plan your trip to Orange Beach by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Orange Beach ranges from 4.2 - 7.4 inches per month. July is typically the wettest month, when rainfall can reach 7.4 in. May is typically the driest time to visit Orange Beach when rainfall is around 4.2 in.

Temperature in Orange Beach by month

Plan your trip to Orange Beach by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Orange Beach, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 January 30, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from Chicago to Orange Beach have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Delta
8.0
Very good
8,450 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

United Airlines
7.4
Good
8,906 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Spirit Airlines
6.3
Okay
8,083 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore 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.

  • 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 $41. Frontier flights start at $55 while deals on Southwest 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: SkyWest Airlines (84%), United Airlines (80%), Air New Zealand (75%).

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

    While on average a flight from Chicago to Orange Beach is generally $356, our data shows the cheapest flight currently is $124. When looking at the most popular route, (Chicago O'Hare Intl - Pensacola), you can expect to pay $140 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 $306). Flying from Chicago to Orange Beach in March is currently the most expensive (average of $418). 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.

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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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$169FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$100Average$192FlexibilityNo cancel feeOn-time65%
DeltaCheapest$199Average$375FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$379FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$228Average$419FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$235Average$459FlexibilityNo cancel feeOn-time69%
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