
$29 Cheap flight deals from Chicago (CHI) to Sunny Isles Beach (MIA)
This Weekend's Flight Deals from Chicago to Sunny Isles Beach
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
MDW
Midway Intl.
MIA
Miami Intl.
$287 Roundtrip, found 5 days ago
$287
Roundtrip
found 5 days ago
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$300 Roundtrip, just found
$300
Roundtrip
just found
ORD
O'Hare Intl.
MIA
Miami Intl.
$313 Roundtrip, found 3 hours ago
$313
Roundtrip
found 3 hours ago
Airfares from $29 One Way, $56 Round Trip from Chicago to Sunny Isles Beach
Prices starting at $56 for return flights and $29 for one-way flights to Sunny Isles Beach were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
FLL
Fort Lauderdale
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
ORD
Chicago
FLL
Fort Lauderdale
$169 Roundtrip, found 21 hours ago
$169
Roundtrip
found 21 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$169 Roundtrip, found 3 hours ago
$169
Roundtrip
found 3 hours ago
MDW
Chicago
FLL
Fort Lauderdale
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
RFD
Rockford
MIA
Miami
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Sunny Isles Beach economy flight packages
Price found within the past 48 hours. Click for updated prices.



3.5-star property
President Hotel
8.4/10 Very Good! (2,302 reviews)
Jun 23 - Jun 29
6 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,195, price is now $1,108 per person
$1,108
per person
found 1 day ago
the location and breakfast and some of the staff are clearly a great value. However the bathroom in general are not at par with a 2* star hotel. The closet door was broken. The shower only had a curtain and floor corners had signs of aging and sticky. On second day while I was on a work call, the house keeping lady comes in and even if I told her to come later as I’m in a call, she didn’t bother she kept coming in and dumped towels on my luggage and was checking the closet door. I told her to go and come back. She have a look and left and that day they didn’t clean the room. The bathroom soap gel was not refilled on day 2 as the lady decided not to come. And you are given only 1 travel size gel. The 3rd day was pleasant. But overall for what I paid I was tad upset.
In short I will have marked it as very good if the housekeeping didn’t mess up and bathroom has more soap and was not sticky.
Reviewed on Apr 17, 2026
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View all tripsSunny Isles Beach business class flight packages
Price found within the past 48 hours. Click for updated prices.

3.5-star property
President Hotel
8.4/10 Very Good! (2,302 reviews)
Jul 2 - Jul 9
7 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,147, price is now $1,259 per person
$1,259
per person
found 2 hours ago
the location and breakfast and some of the staff are clearly a great value. However the bathroom in general are not at par with a 2* star hotel. The closet door was broken. The shower only had a curtain and floor corners had signs of aging and sticky. On second day while I was on a work call, the house keeping lady comes in and even if I told her to come later as I’m in a call, she didn’t bother she kept coming in and dumped towels on my luggage and was checking the closet door. I told her to go and come back. She have a look and left and that day they didn’t clean the room. The bathroom soap gel was not refilled on day 2 as the lady decided not to come. And you are given only 1 travel size gel. The 3rd day was pleasant. But overall for what I paid I was tad upset.
In short I will have marked it as very good if the housekeeping didn’t mess up and bathroom has more soap and was not sticky.
Reviewed on Apr 17, 2026

3.5-star property
The Penguin Hotel
8.2/10 Very Good! (1,830 reviews)
Jul 2 - Jul 9
7 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,170, price is now $1,281 per person
$1,281
per person
found 2 hours ago
I up graded my room from an ocean view to an ocean view suite, it was great
Reviewed on Mar 2, 2026

5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,501 reviews)
Jul 2 - Jul 9
7 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $6,125, price is now $3,664 per person
$3,664
per person
found 2 hours ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
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See all available trips from Chicago to Sunny Isles Beach
View all tripsSunny Isles Beach first class flight packages
Price found within the past 48 hours. Click for updated prices.

5.0-star property
Kimpton EPIC Hotel by IHG
9/10 Wonderful! (2,450 reviews)
Jun 18 - Jun 21
3 night stay
Chicago (ORD) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (ORD)
American Airlines • FirstClass
Price was $1,711, price is now $1,416 per person
$1,416
per person
found 7 hours ago
A great place to stay if you have to spend some time in Brickell
Reviewed on Apr 29, 2026

5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,501 reviews)
Jun 18 - Jun 21
3 night stay
Chicago (ORD) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (ORD)
American Airlines • FirstClass
Price was $2,975, price is now $2,225 per person
$2,225
per person
found 7 hours ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026

4.0-star property
The Shelborne By Proper, a Member of Design Hotels
9.4/10 Exceptional! (173 reviews)
Jun 18 - Jun 21
3 night stay
Chicago (ORD) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (ORD)
American Airlines • FirstClass
Price was $2,095, price is now $1,692 per person
$1,692
per person
found 7 hours ago
Don't see what you're looking for?
See all available trips from Chicago to Sunny Isles Beach
View all tripsMore About Flying To Sunny Isles Beach from Chicago
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- Car rentals in Miami
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- Car rentals at Fort Lauderdale Airport (FLL)
- Flights to Fort Lauderdale
- Hotels in South Beach



