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Orange Beach

$69+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
May 6 — May 131
Tue 5/6
Tue 5/13
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 84 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$166
(Cheapflightsfares)

One-way from

$69
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$375
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 ($10 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/135:05 amORD - PNS
1 stop10h 25mSpirit Airlines
Sat 5/176:14 pmPNS - ORD
1 stop5h 15mSpirit Airlines
Deal found 4/29$166
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1310:40 amORD - PNS
Nonstop2h 28mUnited Airlines
Sat 5/172:05 pmPNS - ORD
Nonstop2h 41mUnited Airlines
Deal found 4/29$177
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 5/136:45 amMDW - PNS
1 stop4h 00mSouthwest
Sat 5/174:15 pmPNS - MDW
Nonstop2h 10mSouthwest
Deal found 4/29$187
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 6/185:35 amORD - PNS
1 stop5h 03mDelta
Sun 6/227:30 pmPNS - ORD
1 stop4h 28mDelta
Deal found 4/30$197
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/188:15 amORD - PNS
Nonstop2h 24mAmerican Airlines
Sun 5/2512:07 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 4/30$203
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/56:00 amMDW - PNS
1 stop6h 50mDelta
Tue 6/174:07 pmPNS - MDW
1 stop5h 38mDelta
Deal found 4/30$218
This Southwest deal was found by Cheapflights users on 5/1. 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.
Fri 6/134:00 pmORD - PNS
1 stop6h 55mSouthwest
Tue 6/176:50 amPNS - ORD
1 stop5h 55mSouthwest
Deal found 5/1$267
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/811:45 amORD - PNS
2 stops19h 40mMultiple Airlines
Sat 5/106:14 pmPNS - ORD
1 stop5h 15mMultiple Airlines
Deal found 4/30$283
This Frontier deal was found by Cheapflights users on 5/1. 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.
Fri 5/306:00 amORD - PNS
1 stop9h 23mFrontier
Mon 6/24:29 pmPNS - ORD
1 stop7h 30mFrontier
Deal found 5/1$290
This Gotogate deal was found by Cheapflights users on 4/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1312:35 pmMDW - PNS
1 stop26h 54mFrontier
Fri 6/204:29 pmPNS - MDW
1 stop28h 24mFrontier
Deal found 4/30$436
This Mytrip deal was found by Cheapflights users on 5/1. 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 5/238:04 pmMDW - PNS
3 stops26h 16mMultiple Airlines
Wed 5/284:35 pmPNS - MDW
3 stops26h 55mMultiple Airlines
Deal found 5/1$540

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 May 1, 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

Tue 5/13

5:05 am-3:30 pm

1 stop10h 25m

Pensacola

Sat 5/17

6:14 pm-11:29 pm

1 stop5h 15m

$166

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 5/13

10:40 am-1:08 pm

Nonstop2h 28m

Pensacola

Sat 5/17

2:05 pm-4:46 pm

Nonstop2h 41m

$177

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 5/13

6:45 am-10:45 am

1 stop4h 00m

Pensacola

Sat 5/17

4:15 pm-6:25 pm

Nonstop2h 10m

$187

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 6/18

5:35 am-10:38 am

1 stop5h 03m

Pensacola

Sun 6/22

7:30 pm-11:58 pm

1 stop4h 28m

$197

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 5/18

8:15 am-10:39 am

Nonstop2h 24m

Pensacola

Sun 5/25

12:07 pm-2:49 pm

Nonstop2h 42m

$203

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Thu 6/5

6:00 am-12:50 pm

1 stop6h 50m

Pensacola

Tue 6/17

4:07 pm-9:45 pm

1 stop5h 38m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 6/13

4:00 pm-10:55 pm

1 stop6h 55m

Pensacola

Tue 6/17

6:50 am-12:45 pm

1 stop5h 55m

$267

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 5/30

6:00 am-3:23 pm

1 stop9h 23m

Pensacola

Mon 6/2

4:29 pm-11:59 pm

1 stop7h 30m

$290

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 6/17

5:05 am-10:37 pm

3 stops41h 32m

Pensacola

Mon 6/23

9:28 am-8:23 pm

2 stops34h 55m

$325

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 6/13

12:35 pm-3:29 pm

1 stop26h 54m

Pensacola

Fri 6/20

4:29 pm-8:53 pm

1 stop28h 24m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 22 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 April 25, 2025.

The best time to book flights from Chicago to Orange Beach is 84 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 May 1, 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.

Weekly flight availability from Chicago to Orange Beach

Explore weekly flight availability from Chicago to Orange Beach. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 1, 2025.

The most flights from CHI to OB9 are scheduled on a Monday (2 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).

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 May 1, 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
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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
7,963 reviews
Southwest
8.0
Very good
4,293 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.1

Entertainment

7.6

Boarding

8.2

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 $69. American Airlines flights start at $89 while deals on Southwest start at $89 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: American Airlines (100%), Envoy Air (100%), Spirit Airlines (89%).

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

    While on average a flight from Chicago to Orange Beach is generally $315, our data shows the cheapest flight currently is $104. When looking at the most popular route, (Chicago O'Hare Intl - Pensacola), you can expect to pay $146 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.

See more FAQs

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$92Average$167FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$205FlexibilityNo cancel feeOn-time65%
DeltaCheapest$199Average$333FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$383FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$374FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$430FlexibilityNo cancel feeOn-time69%

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