$72+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Mar 14 — Mar 211
1 adult, Economy
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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 November or May, booked 77 days in advance, depart on a Tuesday or Sunday and return on a Thursday
Cheap flight deals from Chicago to Rosemary Beach
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Cheapest flights from Chicago to Rosemary BeachExplore 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 February 12, 2026.
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 February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/8. 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 4/115:00 am
MDW
- ECP
2 stops9h 00m
Southwest
Sat 4/187:20 am
ECP
- MDW
2 stops9h 50m
Southwest
Deal found 2/8![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 2/8. 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 5/152:59 pm
ORD
- ECP
1 stop4h 10m
Delta
Sat 5/161:50 pm
ECP
- ORD
1 stop6h 44m
Delta
Deal found 2/8![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 2/8. 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 4/185:21 pm
MDW
- ECP
1 stop5h 51m
Delta
Thu 4/237:05 am
ECP
- MDW
1 stop5h 02m
Delta
Deal found 2/8![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 2/8. 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 5/1011:15 am
MDW
- ECP
Nonstop2h 10m
Southwest
Sat 5/166:25 pm
ECP
- MDW
1 stop4h 10m
Southwest
Deal found 2/8![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 2/10. 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 5/912:55 pm
ORD
- ECP
Nonstop2h 25m
Southwest
Tue 5/127:15 am
ECP
- ORD
1 stop5h 35m
Southwest
Deal found 2/10![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 2/10. 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 3/102:30 pm
MDW
- ECP
Nonstop2h 10m
Southwest
Tue 3/171:20 pm
ECP
- MDW
1 stop3h 45m
Southwest
Deal found 2/10![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/8. 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 2/286:30 pm
ORD
- ECP
1 stop4h 09m
Delta
Thu 3/56:06 pm
ECP
- ORD
1 stop5h 50m
Delta
Deal found 2/8![Delta logo]()
$220
This Southwest deal was found by Cheapflights users on 2/11. 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.
Thu 4/911:40 am
MDW
- ECP
1 stop9h 50m
Southwest
Mon 4/135:00 pm
ECP
- MDW
Nonstop2h 25m
Southwest
Deal found 2/11![Southwest logo]()
$223
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 3/211:58 am
ORD
- ECP
Nonstop2h 26m
American Airlines
Fri 3/63:00 pm
ECP
- ORD
Nonstop2h 45m
American Airlines
Deal found 2/10![American Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/7. 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 3/26:40 pm
MDW
- ECP
1 stop3h 59m
Delta
Thu 3/56:00 am
ECP
- MDW
1 stop3h 54m
Delta
Deal found 2/7![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/8. 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 2/225:15 am
MDW
- ECP
1 stop6h 40m
Southwest
Sat 2/285:10 pm
ECP
- MDW
1 stop5h 40m
Southwest
Deal found 2/8![Southwest logo]()
$228
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/410:18 am
ORD
- ECP
Nonstop2h 26m
American Airlines
Wed 3/117:19 am
ECP
- ORD
1 stop6h 15m
American Airlines
Deal found 2/9![American Airlines logo]()
$229
Best flights from Chicago to Rosemary BeachDiscover carefully curated flight deals from Chicago to Rosemary Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Chicago to Rosemary Beach that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This Delta deal was found by Cheapflights users on 2/8. 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 2/286:30 pm
ORD
- ECP
1 stop4h 09m
Delta
Mon 3/26:06 pm
ECP
- ORD
1 stop5h 50m
Delta
Deal found 2/8![Delta logo]()
$220
This Southwest deal was found by Cheapflights users on 2/10. 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 5/98:00 am
MDW
- ECP
Nonstop2h 10m
Southwest
Tue 5/127:15 am
ECP
- MDW
2 stops8h 30m
Southwest
Deal found 2/10![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Thu 3/127:10 am
ORD
- ECP
Nonstop2h 33m
United Airlines
Mon 3/1610:24 am
ECP
- ORD
Nonstop2h 44m
United Airlines
Deal found 2/11![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 2/8. 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 3/107:10 am
ORD
- ECP
1 stop5h 35m
Delta
Tue 3/176:00 am
ECP
- ORD
1 stop4h 00m
Delta
Deal found 2/8![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/8. 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 4/118:00 am
MDW
- ECP
Nonstop2h 10m
Southwest
Sat 4/189:55 am
ECP
- MDW
1 stop7h 35m
Southwest
Deal found 2/8![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 2/9. 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 5/62:25 pm
ORD
- ECP
1 stop5h 11m
Delta
Sat 5/96:00 am
ECP
- ORD
1 stop7h 01m
Delta
Deal found 2/9![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/9. 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 4/46:25 am
MDW
- ECP
1 stop6h 05m
Southwest
Thu 4/97:00 pm
ECP
- MDW
1 stop3h 45m
Southwest
Deal found 2/9![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 2/7. 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 3/212:45 pm
MDW
- ECP
1 stop6h 45m
Delta
Wed 3/48:03 am
ECP
- MDW
1 stop3h 56m
Delta
Deal found 2/7![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/7. 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 3/312:45 pm
MDW
- ECP
1 stop6h 07m
Delta
Thu 3/54:04 pm
ECP
- MDW
1 stop6h 27m
Delta
Deal found 2/7![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/7. 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 3/36:00 am
MDW
- ECP
1 stop5h 25m
Delta
Tue 3/35:00 pm
ECP
- MDW
1 stop5h 33m
Delta
Deal found 2/7![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/7. 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 3/212:45 pm
MDW
- ECP
1 stop6h 45m
Delta
Fri 3/66:06 pm
ECP
- MDW
1 stop4h 25m
Delta
Deal found 2/7![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/8. 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 3/106:00 am
MDW
- ECP
1 stop6h 45m
Delta
Tue 3/176:00 am
ECP
- MDW
1 stop6h 02m
Delta
Deal found 2/8![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/7. 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 3/36:40 pm
MDW
- ECP
1 stop3h 59m
Delta
Fri 3/66:00 am
ECP
- MDW
1 stop3h 54m
Delta
Deal found 2/7![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/7. 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 3/412:45 pm
MDW
- ECP
1 stop6h 07m
Delta
Thu 3/56:00 am
ECP
- MDW
1 stop3h 54m
Delta
Deal found 2/7![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 2/10. 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 3/185:30 am
ORD
- ECP
1 stop4h 53m
Delta
Tue 3/245:30 pm
ECP
- ORD
1 stop6h 24m
Delta
Deal found 2/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 2/10. 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 5/125:59 pm
ORD
- ECP
1 stop4h 52m
Delta
Tue 5/191:50 pm
ECP
- ORD
1 stop4h 51m
Delta
Deal found 2/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 2/11. 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 4/59:40 am
ORD
- ECP
1 stop5h 56m
Delta
Wed 4/85:30 pm
ECP
- ORD
1 stop6h 24m
Delta
Deal found 2/11![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 2/10. 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 5/109:44 am
ORD
- ECP
1 stop4h 20m
Delta
Thu 5/146:00 am
ECP
- ORD
1 stop4h 06m
Delta
Deal found 2/10![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 2/7. 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 2/284:13 pm
MDW
- ECP
1 stop6h 26m
Delta
Sat 3/79:26 am
ECP
- MDW
1 stop5h 55m
Delta
Deal found 2/7![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 2/7. 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 2/284:13 pm
MDW
- ECP
1 stop6h 26m
Delta
Tue 3/35:00 pm
ECP
- MDW
1 stop5h 33m
Delta
Deal found 2/7![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 2/8. 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 2/226:45 am
ORD
- ECP
1 stop6h 35m
Delta
Mon 3/26:06 pm
ECP
- ORD
1 stop5h 50m
Delta
Deal found 2/8![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 2/8. 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 2/2411:18 am
ORD
- ECP
1 stop4h 57m
Delta
Thu 3/56:00 am
ECP
- ORD
1 stop4h 14m
Delta
Deal found 2/8![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 2/8. 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 2/215:25 am
ORD
- ECP
1 stop6h 00m
Delta
Wed 2/255:00 pm
ECP
- ORD
1 stop6h 56m
Delta
Deal found 2/8![Delta logo]()
$268
Last-minute flights from Chicago to Rosemary BeachDiscover last-minute flight deals from Chicago to Rosemary Beach. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Rosemary Beach. Data last updated February 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/8. 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 2/226:45 am
ORD
- ECP
1 stop6h 35m
Delta
Sat 2/289:26 am
ECP
- ORD
1 stop4h 44m
Delta
Deal found 2/8![Delta logo]()
$240
This Delta deal was found by Cheapflights users on 2/8. 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 2/2411:18 am
ORD
- ECP
1 stop4h 57m
Delta
Mon 3/26:06 pm
ECP
- ORD
1 stop5h 50m
Delta
Deal found 2/8![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 2/8. 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 2/286:30 pm
ORD
- ECP
1 stop4h 09m
Delta
Mon 3/26:06 pm
ECP
- ORD
1 stop5h 50m
Delta
Deal found 2/8![Delta logo]()
$220
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 3/211:58 am
ORD
- ECP
Nonstop2h 26m
American Airlines
Thu 3/51:19 pm
ECP
- ORD
Nonstop2h 45m
American Airlines
Deal found 2/10![American Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/10. 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 3/36:40 pm
MDW
- ECP
1 stop3h 59m
Delta
Wed 3/48:03 am
ECP
- MDW
1 stop3h 56m
Delta
Deal found 2/10![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 2/9. 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 3/410:18 am
ORD
- ECP
Nonstop2h 26m
American Airlines
Wed 3/117:19 am
ECP
- ORD
1 stop6h 15m
American Airlines
Deal found 2/9![American Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 2/9. 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 3/42:46 pm
ORD
- ECP
1 stop4h 06m
Delta
Wed 3/1112:28 pm
ECP
- ORD
1 stop6h 13m
Delta
Deal found 2/9![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 2/10. 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 3/102:30 pm
MDW
- ECP
Nonstop2h 10m
Southwest
Tue 3/171:20 pm
ECP
- MDW
1 stop3h 45m
Southwest
Deal found 2/10![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Thu 3/127:10 am
ORD
- ECP
Nonstop2h 33m
United Airlines
Mon 3/1610:24 am
ECP
- ORD
Nonstop2h 44m
United Airlines
Deal found 2/11![United Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 2/9. 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 3/242:30 pm
MDW
- ECP
Nonstop2h 10m
Southwest
Thu 3/262:45 pm
ECP
- MDW
1 stop10h 10m
Southwest
Deal found 2/9![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 2/10. 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.
Mon 3/304:05 pm
MDW
- ECP
1 stop4h 30m
Southwest
Tue 4/77:55 am
ECP
- MDW
1 stop7h 30m
Southwest
Deal found 2/10![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 3/307:00 am
ORD
- ECP
Nonstop2h 38m
United Airlines
Tue 4/710:29 am
ECP
- ORD
Nonstop2h 46m
United Airlines
Deal found 2/10![United Airlines logo]()
$246
One-way flights from Chicago to Rosemary BeachSearch for one-way flight options from Chicago to Rosemary Beach. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Chicago to Rosemary Beach. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Southwest deal was found by Cheapflights users on 2/9. 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 3/78:05 am
MDW
- ECP
Nonstop2h 20m
Southwest
Deal found 2/9![Southwest logo]()
$72
This Southwest deal was found by Cheapflights users on 2/9. 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 3/72:40 pm
ORD
- ECP
1 stop5h 45m
Southwest
Deal found 2/9![Southwest logo]()
$82
This Southwest deal was found by Cheapflights users on 2/9. 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 4/115:00 am
MDW
- ECP
2 stops9h 00m
Southwest
Deal found 2/9![Southwest logo]()
$87
This Southwest deal was found by Cheapflights users on 2/9. 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 2/285:40 am
MDW
- ECP
1 stop3h 45m
Southwest
Deal found 2/9![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 2/9. 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 4/185:59 pm
ORD
- ECP
1 stop5h 13m
Delta
Deal found 2/9![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 2/8. 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 5/96:30 am
MDW
- ECP
1 stop6h 14m
Delta
Deal found 2/8![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 2/9. 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 4/1112:55 pm
ORD
- ECP
Nonstop2h 25m
Southwest
Deal found 2/9![Southwest logo]()
$102
This Southwest deal was found by Cheapflights users on 2/8. 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 5/28:00 am
MDW
- ECP
Nonstop2h 10m
Southwest
Deal found 2/8![Southwest logo]()
$102
This United Airlines deal was found by Cheapflights users on 2/11. 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.
Wed 3/117:10 am
ORD
- ECP
Nonstop2h 33m
United Airlines
Deal found 2/11![United Airlines logo]()
$104
This Southwest deal was found by Cheapflights users on 2/9. 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.
Thu 3/53:05 pm
MDW
- ECP
Nonstop2h 15m
Southwest
Deal found 2/9![Southwest logo]()
$104
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Mon 4/611:58 am
ORD
- ECP
Nonstop2h 26m
American Airlines
Deal found 2/10![American Airlines logo]()
$106
This Delta deal was found by Cheapflights users on 2/9. 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 2/286:30 pm
ORD
- ECP
1 stop4h 09m
Delta
Deal found 2/9![Delta logo]()
$107
Find 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 February 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Southwest) |
One-way from | $72 (Southwest) |
Popular in | December |
Cheapest in | November |
Average price | $320 |
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 February 12, 2026.
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
Sat 2/28
6:30 pm-10:39 pm
1 stop4h 09m
Panama City NW Florida Beaches
Mon 3/2
6:06 pm-11:56 pm
1 stop5h 50m
$220
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Sat 5/9
8:00 am-10:10 am
Nonstop2h 10m
Panama City NW Florida Beaches
Tue 5/12
7:15 am-3:45 pm
2 stops8h 30m
$222
ChicagoPanama City
ORD - ECP
ORDECP
Chicago O'Hare Intl
Tue 3/10
7:10 am-12:45 pm
1 stop5h 35m
Panama City NW Florida Beaches
Tue 3/17
6:00 am-10:00 am
1 stop4h 00m
$227
ChicagoPanama City
ORD - ECP
ORDECP
Chicago O'Hare Intl
Wed 5/6
2:25 pm-7:36 pm
1 stop5h 11m
Panama City NW Florida Beaches
Sat 5/9
6:00 am-1:01 pm
1 stop7h 01m
$227
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Mon 3/2
12:45 pm-7:30 pm
1 stop6h 45m
Panama City NW Florida Beaches
Wed 3/4
8:03 am-11:59 am
1 stop3h 56m
$227
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Tue 3/3
12:45 pm-6:52 pm
1 stop6h 07m
Panama City NW Florida Beaches
Thu 3/5
4:04 pm-10:31 pm
1 stop6h 27m
$227
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Tue 3/3
6:00 am-11:25 am
1 stop5h 25m
Panama City NW Florida Beaches
Tue 3/3
5:00 pm-10:33 pm
1 stop5h 33m
$227
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Mon 3/2
12:45 pm-7:30 pm
1 stop6h 45m
Panama City NW Florida Beaches
Fri 3/6
6:06 pm-10:31 pm
1 stop4h 25m
$227
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Tue 3/10
6:00 am-12:45 pm
1 stop6h 45m
Panama City NW Florida Beaches
Tue 3/17
6:00 am-12:02 pm
1 stop6h 02m
$227
ChicagoPanama City
MDW - ECP
MDWECP
Chicago Midway
Tue 3/3
6:40 pm-10:39 pm
1 stop3h 59m
Panama City NW Florida Beaches
Fri 3/6
6:00 am-9:54 am
1 stop3h 54m
$227
Showing 1-10 of 46 results
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.
ORD-ECP
MDW-ECP
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
CHI-RB9
ORD-ECP
MDW-ECP
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 February 6, 2026.
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 77 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 $209). 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 February 12, 2026.
It’s typically best to fly out from Chicago to Rosemary Beach in the evening. Doing so could potentially save you 11% on the flight price compared to flying at noon, which is usually more expensive.
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 February 12, 2026.
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.
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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.
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Complete your trip
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Find flights from Chicago to Rosemary Beach, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Rosemary Beach flights
Browse other Chicago and Rosemary Beach flight options. Last updated on February 12, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$170 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$116 | Average$210 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$133 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$207 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$209 | Average$403 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$363 | FlexibilityNo cancel fee | On-time63% |