$105 Find Cheap Flights from Chicago to Rosemary Beach

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Rosemary Beach departing on 3/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Flight Deals

Cheap Flights from Chicago to Rosemary Beach (CHI-ECP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Rosemary Beach that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Rosemary Beach

Thu, Mar 5 - Thu, Mar 26
Southwest Logo
3:05 pm - 5:20 pmMDW-ECP
2h 15mnonstop
Southwest Logo
5:55 pm - 11:00 pmECP-MDW
5h 05m1 stop
$219Southwest
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Mon, Dec 8 - Sat, Dec 13
Delta Logo
6:45 am - 12:47 pmORD-ECP
6h 02m1 stop
Delta Logo
1:32 pm - 6:43 pmECP-ORD
5h 11m1 stop
$229Delta
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Mon, Dec 8 - Sat, Dec 13
Delta Logo
5:29 pm - 11:06 pmMDW-ECP
5h 37m1 stop
Delta Logo
10:00 am - 3:44 pmECP-MDW
5h 44m1 stop
$229Delta
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Wed, Dec 3 - Mon, Dec 8
Southwest Logo
8:25 am - 2:40 pmMDW-ECP
6h 15m1 stop
Southwest Logo
10:00 am - 6:25 pmECP-MDW
8h 25m2 stops
$234Southwest
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Mon, Feb 9 - Wed, Feb 18
American Airlines Logo
8:01 am - 1:04 pmORD-ECP
5h 03m1 stop
American Airlines Logo
12:49 pm - 3:29 pmECP-ORD
2h 40mnonstop
$239American Airlines
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Mon, Mar 16 - Sat, Mar 21
Southwest Logo
3:05 pm - 5:20 pmMDW-ECP
2h 15mnonstop
Southwest Logo
7:25 am - 12:00 pmECP-MDW
4h 35m1 stop
$239Southwest
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Tue, Feb 3 - Tue, Feb 10
Southwest Logo
1:45 pm - 6:10 pmORD-ECP
4h 25m1 stop
Southwest Logo
8:00 am - 9:50 pmECP-ORD
13h 50m2 stops
$240Southwest
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Sat, Feb 14 - Sat, Feb 21
Southwest Logo
3:45 pm - 9:00 pmORD-ECP
5h 15m1 stop
Southwest Logo
7:40 am - 12:15 pmECP-ORD
4h 35m1 stop
$249Southwest
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Tue, Feb 17 - Sat, Feb 21
American Airlines Logo
1:15 pm - 9:54 pmORD-ECP
8h 39m1 stop
American Airlines Logo
1:06 pm - 3:46 pmECP-ORD
2h 40mnonstop
$259American Airlines
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Fri, Nov 28 - Tue, Dec 2
American Airlines Logo
7:11 am - 2:07 pmORD-ECP
6h 56m1 stop
American Airlines Logo
5:55 pm - 12:12 amECP-ORD
6h 17m1 stop
$269American Airlines
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Everything you should know

Cheapest round-trip
$219
Overall average: $451
Southwest
Thu 3/5Thu 3/26
MDW - ECP • Non-stop
Cheapest non-stop
$249
Typical prices: $493-$534
American Airlines
Tue 2/17Sat 2/21
ORD - ECP • Non-stop
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We hope you love your trip to Rosemary Beach!
Useful Info

Good to know

Low seasonNovember
Cheapest flight$105
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago Midway Airport to Panama City

When to book flights from Chicago to Rosemary Beach

Are your dates flexible? Find out the best times to travel from Chicago to Rosemary Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Rosemary Beach

  • Which airports will I be using when flying from Chicago to Rosemary Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Rosemary Beach does not have its own airport so you’ll be flying into nearby Panama City NW Florida Beaches airport, which is 14.1 mi away.

  • How long does a flight from Chicago to Rosemary Beach take?

    Direct flights cover the 802 miles separating Chicago and Rosemary Beach in about 2h 15m.

  • How many flights are there between Chicago and Rosemary Beach?

    1 direct flights run between Chicago and Rosemary Beach on a daily basis. On average, there are about 9 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Rosemary Beach?

    Consider leaving on a Thursday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Rosemary Beach?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Rosemary Beach.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Rosemary Beach?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Rosemary Beach from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Rosemary Beach?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Rosemary Beach with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Rosemary Beach?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Rosemary Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Rosemary Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Rosemary Beach found on KAYAK was with Southwest for $105. Southwest offered a round-trip connection from $219 and Delta from $229.

Top tips for finding cheap flights from Chicago to Rosemary Beach

  • There is no airport in Rosemary Beach. Instead, you’ll be flying into Panama City NW Florida Beaches Airport when flying between Chicago and Rosemary Beach.
  • The cheapest flight from Chicago to Rosemary Beach was found 53 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is January.

Reviews of the top 4 airlines serving Chicago to Rosemary Beach

 
Need help choosing which airline to fly with from Chicago to Rosemary Beach? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4235 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Everything you need to know for your flight from Chicago to Rosemary Beach

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