HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Rosemary Beach

$134+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Rosemary Beach with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Rosemary Beach are usually found in January or July, 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 August 28, 2025.

Round-trip from

$287
(Southwest)

One-way from

$134
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$408
From Chicago (CHI) to Rosemary Beach
Search Deals
One-way flight from Chicago (CHI) to Rosemary Beach
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 28, 2025.

This Southwest deal was found by Cheapflights users on 8/28. 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
Wed 9/247:40 amECP - ORD
1 stop5h 05mSouthwest
Deal found 8/28$287
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sat 9/279:20 amMDW - ECP
Nonstop2h 05mSouthwest
Sat 10/49:15 amECP - MDW
Nonstop2h 10mSouthwest
Deal found 8/28$287
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 9/2010:35 amORD - ECP
2 stops12h 28mDelta
Wed 9/242:05 pmECP - ORD
1 stop4h 55mDelta
Deal found 8/28$291
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 9/209:35 amMDW - ECP
2 stops13h 28mDelta
Tue 9/237:00 amECP - MDW
1 stop4h 48mDelta
Deal found 8/28$291
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 9/209:35 amMDW - ECP
2 stops13h 28mDelta
Wed 9/247:00 amECP - MDW
2 stops11h 35mDelta
Deal found 8/28$295
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sat 9/2011:25 amMDW - ECP
1 stop7h 45mSouthwest
Tue 9/239:45 amECP - MDW
1 stop7h 25mSouthwest
Deal found 8/28$297
This Delta deal was found by Cheapflights users on 8/28. 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 9/226:00 amMDW - ECP
1 stop3h 55mDelta
Wed 9/247:00 amECP - MDW
2 stops11h 35mDelta
Deal found 8/28$300
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 9/2010:35 amORD - ECP
2 stops12h 28mDelta
Mon 9/226:54 pmECP - ORD
1 stop5h 00mDelta
Deal found 8/28$301
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sat 9/207:30 amORD - ECP
2 stops9h 25mSouthwest
Tue 9/237:40 amECP - ORD
1 stop5h 05mSouthwest
Deal found 8/28$302
This Delta deal was found by Cheapflights users on 8/28. 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.
Sat 9/276:00 pmORD - ECP
1 stop5h 03mDelta
Sat 10/46:00 amECP - ORD
1 stop7h 01mDelta
Deal found 8/28$307
This Delta deal was found by Cheapflights users on 8/27. 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 12/81:05 pmMDW - ECP
1 stop4h 48mDelta
Sat 12/135:00 pmECP - MDW
1 stop4h 44mDelta
Deal found 8/27$307
This Southwest deal was found by Cheapflights users on 8/28. 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.
Sat 9/276:00 amORD - ECP
2 stops10h 55mSouthwest
Sat 10/44:10 pmECP - ORD
1 stop5h 50mSouthwest
Deal found 8/28$312

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 August 28, 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 10/7

4:05 pm-11:10 pm

1 stop7h 05m

Panama City NW Florida Beaches

Tue 10/28

12:13 pm-8:37 pm

1 stop8h 24m

$287

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

Wed 9/24

7:40 am-12:45 pm

1 stop5h 05m

$287

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Tue 10/14

8:11 am-1:12 pm

1 stop5h 01m

Panama City NW Florida Beaches

Tue 10/21

3:41 pm-10:54 pm

1 stop7h 13m

$287

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Tue 11/4

4:15 pm-11:10 pm

1 stop6h 55m

Panama City NW Florida Beaches

Tue 11/11

6:00 am-12:04 pm

1 stop6h 04m

$287

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Tue 10/14

5:45 am-10:25 am

1 stop4h 40m

Panama City NW Florida Beaches

Tue 10/21

9:50 am-6:05 pm

1 stop8h 15m

$287

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Tue 11/4

5:09 pm-11:10 pm

1 stop6h 01m

Panama City NW Florida Beaches

Tue 11/11

5:00 pm-11:32 pm

1 stop6h 32m

$287

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Sat 9/27

9:20 am-11:25 am

Nonstop2h 05m

Panama City NW Florida Beaches

Sat 10/4

9:15 am-11:25 am

Nonstop2h 10m

$287

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Sat 9/20

10:35 am-11:03 pm

2 stops12h 28m

Panama City NW Florida Beaches

Wed 9/24

2:05 pm-7:00 pm

1 stop4h 55m

$291

ChicagoPanama City

ORD - ECP

ORDECP

Chicago O'Hare Intl

Sat 9/20

10:35 am-11:03 pm

2 stops12h 28m

Panama City NW Florida Beaches

Tue 9/23

2:05 pm-7:00 pm

1 stop4h 55m

$291

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Sat 9/20

9:35 am-11:03 pm

2 stops13h 28m

Panama City NW Florida Beaches

Wed 9/24

4:46 pm-9:36 pm

1 stop4h 50m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/27

Showing 1-10 of 40 results
1
2
3
4

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 August 22, 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 $416). 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 August 28, 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.

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 August 28, 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
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
7,977 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
8,944 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

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.

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

    Delta, Southwest, and American Airlines can get you from Chicago to Rosemary Beach in just under 5h. Your travel time can differ by up to 2h 05m. The distance between Chicago and Rosemary Beach is about 811 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $134 on United Airlines. Other airlines that offer cheap prices include American Airlines from $144 and Delta from $144 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 American Airlines (64%).

  • 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 $307, our data indicates the cheapest price to be $149. The most popular route (Chicago O'Hare Intl - Panama City NW Florida Beaches), is priced around $287.

  • 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 $416). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Rosemary Beach

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Midway to Miami flights
O'Hare Intl to Tampa flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to West Palm Beach flights
Midway to Tampa flights
St. Louis to Orlando flights
Midway to Fort Lauderdale flights
St. Louis to Miami flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Key West flights
O'Hare Intl to Pensacola flights
Midway to West Palm Beach flights
Midway to Fort Myers flights
O'Hare Intl to Panama City flights
Moline to Orlando flights
St. Louis to Tampa flights
St. Louis to Fort Lauderdale flights
Midway to Sarasota flights
O'Hare Intl to Daytona Beach flights
Midway to Key West flights
St. Louis to West Palm Beach flights
Midway to Jacksonville flights
St. Louis to Key West flights
St. Louis to Pensacola flights
Midway to Pensacola flights
St. Louis to Fort Myers flights
Rockford to St Petersburg flights
Moline to Tampa flights
Peoria to Orlando flights
St. Louis to Jacksonville flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Melbourne flights
Bloomington to Orlando flights
St. Louis to Panama City flights
Moline to Fort Myers flights
St. Louis to Sarasota flights
O'Hare Intl to Tallahassee flights
Midway to Panama City flights
Moline to Sarasota flights
St. Louis to Gainesville flights
O'Hare Intl to Valparaiso flights
Evansville to Orlando flights
Moline to Miami flights
Evansville to Pensacola flights
Midway to Daytona Beach flights

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 August 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$143FlexibilityNo cancel feeOn-time88%
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$457FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$212Average$389FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$414FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$439FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.