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Rosemary Beach

$109+ Cheap flights from Chicago (CHI) to Rosemary Beach, FL

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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Rosemary Beach are usually found in January or May, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Rosemary Beach

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

Round-trip from

$217
(United Airlines)

One-way from

$109
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$334
From Chicago (CHI) to Rosemary Beach
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One-way flight from Chicago (CHI) to Rosemary Beach
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Chicago to Rosemary Beach

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

This United Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 8/1210:50 amORD - ECP
Nonstop2h 33mUnited Airlines
Tue 8/191:44 pmECP - ORD
Nonstop2h 39mUnited Airlines
Deal found 7/15$217
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sun 9/141:45 pmMDW - ECP
Nonstop2h 05mSouthwest
Sat 9/204:10 pmECP - MDW
Nonstop2h 10mSouthwest
Deal found 7/15$224
This Southwest deal was found by Cheapflights users on 7/15. 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.
Tue 9/237:30 amORD - ECP
1 stop5h 00mSouthwest
Sat 9/274:10 pmECP - ORD
1 stop5h 50mSouthwest
Deal found 7/15$237
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/206:42 pmMDW - ECP
1 stop4h 24mDelta
Tue 8/265:02 pmECP - MDW
1 stop4h 42mDelta
Deal found 7/15$237
This Delta deal was found by Cheapflights users on 7/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/97:05 amORD - ECP
1 stop6h 03mDelta
Fri 9/126:54 pmECP - ORD
1 stop4h 58mDelta
Deal found 7/15$244
This American Airlines deal was found by Cheapflights users on 7/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:10 amORD - ECP
1 stop6h 10mAmerican Airlines
Mon 10/61:47 pmECP - ORD
1 stop5h 29mAmerican Airlines
Deal found 7/14$251

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Rosemary 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 July 16, 2025.
Use the filters below to find and compare flights from Chicago to Rosemary Beach that are best for you.

Fly from

Chicago

Fly to

Rosemary Beach

Route

Depart

Return

Price

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Tue 8/12

10:50 am-1:23 pm

Nonstop2h 33m

Panama City NW Florida Beaches

Tue 8/19

1:44 pm-4:23 pm

Nonstop2h 39m

$217

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Sun 9/14

1:45 pm-3:50 pm

Nonstop2h 05m

Panama City NW Florida Beaches

Sat 9/20

4:10 pm-6:20 pm

Nonstop2h 10m

$224

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Wed 8/20

6:42 pm-11:06 pm

1 stop4h 24m

Panama City NW Florida Beaches

Tue 8/26

5:02 pm-9:44 pm

1 stop4h 42m

$237

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Tue 9/23

7:30 am-12:30 pm

1 stop5h 00m

Panama City NW Florida Beaches

Sat 9/27

4:10 pm-10:00 pm

1 stop5h 50m

$237

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Tue 9/9

7:05 am-1:08 pm

1 stop6h 03m

Panama City NW Florida Beaches

Fri 9/12

6:54 pm-11:52 pm

1 stop4h 58m

$244

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Fri 10/3

8:10 am-2:20 pm

1 stop6h 10m

Panama City NW Florida Beaches

Mon 10/6

1:47 pm-7:16 pm

1 stop5h 29m

$251

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Tue 8/19

10:35 am-1:03 pm

Nonstop2h 28m

$109

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Sat 8/16

9:20 am-11:25 am

Nonstop2h 05m

$109

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Sat 8/16

6:00 pm-11:06 pm

1 stop5h 06m

$119

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Tue 10/14

6:00 am-10:15 am

1 stop4h 15m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

Showing 1-10 of 12 results
1
2

Best time to book a flight from Chicago to Rosemary Beach

Have a flexible travel schedule? Discover the best time to fly to Rosemary 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 Rosemary Beach

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Rosemary Beach. Price data was last updated on July 11, 2025.

The price you pay for your flight from Chicago to Rosemary Beach may vary depending on when you book. For the best chance of a lower fare, look to book 42 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Rosemary Beach (average of $306). Flying from Chicago to Rosemary Beach in March is currently the most expensive (average of $417). 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 RB9?

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Rosemary Beach as you normally would.

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

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

Travelers seeking maximum savings on their Chicago to Rosemary Beach flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Rosemary Beach

Explore weekly flight availability from Chicago to Rosemary 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 July 16, 2025.

The most flights from CHI to RB9 are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to Rosemary Beach?

Reviews of airlines servicing Rosemary Beach

Get insights into the airlines that provide service to Rosemary 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 Rosemary Beach. Reviews last updated July 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago to Rosemary Beach to help guide your decision. 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
4,239 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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
7,957 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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
8,863 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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
4,239 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.6

Overall

8.0

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 Rosemary 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 Rosemary Beach one-way?

    One-way options have recently been found by users for as low as $109 on United Airlines. Other airlines that offer cheap prices include Southwest from $109 and Delta from $119 one-way.

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

    The top 3 most reliable airlines when flying from Chicago to Rosemary Beach are United Airlines (90%), Air New Zealand (90%) and Envoy Air (83%).

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

    Looking for the cheapest flight from Chicago to Rosemary Beach? While on average our users pay $302, our data indicates the cheapest price to be $138. The most popular route (Chicago O'Hare Intl - Panama City NW Florida Beaches), is priced around $224.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Rosemary 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 Rosemary Beach?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Rosemary Beach (average of $306). Flying from Chicago to Rosemary Beach in March is currently the most expensive (average of $417). 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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Top 6 airlines flying from Chicago to Rosemary Beach

Discover the top 6 airlines that operate flights from Chicago to Rosemary 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 July 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$176FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$452FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$388FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$214Average$410FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$234Average$442FlexibilityNo cancel feeOn-time69%

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