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Rosemary Beach

$105+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Rosemary Beach are usually found in January or September, booked 50 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 November 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$229
(Delta)

One-way from

$107
(Delta)

Popular in

December

Cheapest in

January

Average price

$381
Provider with most accurate pricing for Chicago (CHI)-Panama City NW Florida Beaches flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Panama City NW Florida Beaches flights.
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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 ($11 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 5, 2025.

This Delta deal was found by Cheapflights users on 11/5. 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 12/19:51 amORD - ECP
1 stop5h 35mDelta
Tue 12/25:00 pmECP - ORD
1 stop5h 43mDelta
Deal found 11/5$229
This Delta deal was found by Cheapflights users on 11/5. 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 12/16:00 amMDW - ECP
1 stop6h 47mDelta
Tue 12/26:59 pmECP - MDW
1 stop4h 48mDelta
Deal found 11/5$229
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/33:52 pmORD - ECP
2 stops7h 18mAmerican Airlines
Mon 12/81:23 pmECP - ORD
1 stop6h 08mAmerican Airlines
Deal found 11/5$234
This Southwest deal was found by Cheapflights users on 11/3. 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 12/312:25 pmMDW - ECP
1 stop6h 40mSouthwest
Wed 12/1010:00 amECP - MDW
2 stops8h 25mSouthwest
Deal found 11/3$234
This American Airlines deal was found by Cheapflights users on 11/3. 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 12/33:52 pmORD - ECP
2 stops7h 18mAmerican Airlines
Wed 12/108:30 amECP - ORD
2 stops8h 21mAmerican Airlines
Deal found 11/3$239
This Delta deal was found by Cheapflights users on 11/4. 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 12/241:22 pmORD - ECP
1 stop4h 53mDelta
Sun 12/287:02 pmECP - ORD
1 stop5h 01mDelta
Deal found 11/4$244
This Southwest deal was found by Cheapflights users on 11/2. 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 11/181:45 pmORD - ECP
1 stop5h 20mSouthwest
Tue 11/257:30 amECP - ORD
1 stop4h 45mSouthwest
Deal found 11/2$249
This Delta deal was found by Cheapflights users on 11/3. 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.
Fri 11/286:00 amMDW - ECP
1 stop6h 47mDelta
Tue 12/26:59 pmECP - MDW
1 stop4h 48mDelta
Deal found 11/3$249
This Delta deal was found by Cheapflights users on 11/5. 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.
Sun 11/306:00 amMDW - ECP
1 stop4h 26mDelta
Tue 12/26:59 pmECP - MDW
1 stop4h 48mDelta
Deal found 11/5$254
This Delta deal was found by Cheapflights users on 11/5. 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 11/196:15 pmORD - ECP
1 stop4h 22mDelta
Sun 11/236:40 pmECP - ORD
1 stop5h 22mDelta
Deal found 11/5$269
This Delta deal was found by Cheapflights users on 11/5. 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 11/196:00 amMDW - ECP
1 stop6h 47mDelta
Sun 11/236:00 amECP - MDW
1 stop5h 52mDelta
Deal found 11/5$269
This American Airlines deal was found by Cheapflights users on 11/4. 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 11/199:53 amORD - ECP
2 stops6h 51mAmerican Airlines
Sun 11/232:37 pmECP - ORD
1 stop4h 41mAmerican Airlines
Deal found 11/4$274

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 November 5, 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

MDW - ECP

MDWECP

Chicago Midway

Mon 2/9

5:25 am-9:35 am

1 stop4h 10m

Panama City NW Florida Beaches

Wed 2/18

3:45 pm-10:05 pm

1 stop6h 20m

$213

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Sat 2/21

6:30 pm-10:45 pm

1 stop4h 15m

Panama City NW Florida Beaches

Sat 2/28

12:15 pm-4:56 pm

1 stop4h 41m

$229

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Fri 11/28

5:13 pm-11:07 pm

1 stop5h 54m

Panama City NW Florida Beaches

Tue 12/2

5:00 pm-10:43 pm

1 stop5h 43m

$229

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Sat 2/21

5:40 am-9:25 am

1 stop3h 45m

Panama City NW Florida Beaches

Sat 2/28

5:10 pm-10:50 pm

1 stop5h 40m

$229

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Mon 12/1

5:23 am-10:26 am

1 stop5h 03m

Panama City NW Florida Beaches

Mon 12/8

6:00 am-12:01 pm

1 stop6h 01m

$229

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Mon 12/1

9:51 am-3:26 pm

1 stop5h 35m

Panama City NW Florida Beaches

Tue 12/2

5:00 pm-10:43 pm

1 stop5h 43m

$229

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Sun 1/11

7:05 am-12:47 pm

1 stop5h 42m

Panama City NW Florida Beaches

Fri 1/16

5:14 pm-11:57 pm

1 stop6h 43m

$229

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Tue 3/17

1:05 pm-6:58 pm

1 stop5h 53m

Panama City NW Florida Beaches

Mon 3/23

11:15 am-4:25 pm

1 stop5h 10m

$229

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Mon 12/1

5:34 pm-11:07 pm

1 stop5h 33m

Panama City NW Florida Beaches

Wed 12/3

5:00 pm-11:47 pm

1 stop6h 47m

$229

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Sun 1/11

6:45 am-12:47 pm

1 stop6h 02m

Panama City NW Florida Beaches

Fri 1/16

5:14 pm-10:09 pm

1 stop4h 55m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 42 results
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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 October 31, 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 50 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, July is the cheapest month in which you can book a flight from Chicago to Rosemary Beach (average of $81). Flying from Chicago to Rosemary Beach in December is currently the most expensive (average of $200). 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 November 5, 2025.

It’s typically best to fly out from Chicago to Rosemary Beach in the evening. Doing so could potentially save you 51% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 Sunday mornings when fares are most often at their lowest. Monday at noon 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 November 5, 2025.

The most flights from CHI to RB9 are scheduled on a Monday (3 on average). You will have fewer flight options on Friday, 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 November 5, 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
4,240 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

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
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

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
7.9
Good
8,004 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

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
9,002 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

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
11,042 reviews
Southwest
8.0
Very good
4,240 reviews

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

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 Rosemary 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 Rosemary Beach?

    Southwest and Delta can get you from Chicago to Rosemary Beach in just under 4h 10m. Your travel time can differ by up to 1h 52m. The distance between Chicago and Rosemary Beach is about 796 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $271, our data indicates the cheapest price to be $104. The most popular route (Chicago O'Hare Intl - Panama City NW Florida Beaches), is priced around $229.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Rosemary Beach (average of $81). Flying from Chicago to Rosemary Beach in December is currently the most expensive (average of $200). 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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Alternative routes for Chicago to Rosemary Beach

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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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$85Average$168FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$414FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$390FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$417FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$421FlexibilityNo cancel feeOn-time69%

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