$24 Cheap flight deals from Chicago (CHI) to Surfside (MIA)

This Weekend's Flight Deals from Chicago to Surfside

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.

Sun, Oct 11 - Thu, Oct 15
RFD
Greater Rockford
FLL
Fort Lauderdale - Hollywood Intl.
$116 Roundtrip, found 3 days ago
$116
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sun, Oct 11 from Greater Rockford to Fort Lauderdale - Hollywood Intl., returning Thu, Oct 15, priced at $116 found 3 days ago
Sat, Oct 10 - Sat, Oct 24
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$300 Roundtrip, found 4 hours ago
$300
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, Oct 10 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Oct 24, priced at $300 found 4 hours ago
Sat, Oct 10 - Tue, Oct 13
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$378 Roundtrip, found 15 hours ago
$378
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Oct 13, priced at $378 found 15 hours ago
Sat, Oct 10 - Wed, Oct 14
MDW
Midway Intl.
MIA
Miami Intl.
$387 Roundtrip, found 1 day ago
$387
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Midway Intl. to Miami Intl., returning Wed, Oct 14, priced at $387 found 1 day ago

Airfares from $24 One Way, $68 Round Trip from Chicago to Surfside

Prices starting at $68 for return flights and $24 for one-way flights to Surfside were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Oct 20 - Thu, Oct 29
ORD
Chicago
FLL
Fort Lauderdale
$68 Roundtrip, found 13 hours ago
$68
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Chicago to Fort Lauderdale, returning Thu, Oct 29, priced at $68 found 13 hours ago
Sun, Oct 25 - Thu, Oct 29
RFD
Rockford
FLL
Fort Lauderdale
$76 Roundtrip, found 6 days ago
$76
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Sun, Oct 25 from Rockford to Fort Lauderdale, returning Thu, Oct 29, priced at $76 found 6 days ago
Sat, Oct 31 - Tue, Nov 10
ORD
Chicago
FLL
Fort Lauderdale
$121 Roundtrip, found 4 hours ago
$121
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Oct 31 from Chicago to Fort Lauderdale, returning Tue, Nov 10, priced at $121 found 4 hours ago
Tue, Dec 15 - Thu, Dec 17
MDW
Chicago
FLL
Fort Lauderdale
$130 Roundtrip, found 14 hours ago
$130
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Tue, Dec 15 from Chicago to Fort Lauderdale, returning Thu, Dec 17, priced at $130 found 14 hours ago
Tue, Nov 10 - Sat, Nov 14
ORD
Chicago
FLL
Fort Lauderdale
$135 Roundtrip, found 2 hours ago
$135
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Nov 10 from Chicago to Fort Lauderdale, returning Sat, Nov 14, priced at $135 found 2 hours ago

Surfside economy flight packages

Price found within the past 48 hours. Click for updated prices.
Barcelona Studios Guesthouse
2.0-star property

Barcelona Studios Guesthouse

9.4/10 Exceptional! (267 reviews)

Nov 10 - Nov 14

4 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $646, price is now $385 per person
$385
per person
found 1 day ago
Great but no tv in the room

Reviewed on Sep 30, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Nov 13 - Nov 17

4 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Price was $15,470, price is now $8,425 per person
$8,425
per person
found 17 hours ago
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

The Penguin Hotel
3.5-star property

The Penguin Hotel

8.4/10 Very Good! (1,996 reviews)

Nov 10 - Nov 14

4 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $833, price is now $509 per person
$509
per person
found 1 day ago
It was a cute little hotel right on the beach

Reviewed on Oct 5, 2026

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Surfside packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,008 reviews)

Nov 6 - Nov 9

3 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,191, price is now $813 per person
$813
per person
found 1 day ago

Bentley Hotel South Beach
4.0-star property

Bentley Hotel South Beach

9.4/10 Exceptional! (1,154 reviews)

Nov 6 - Nov 9

3 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,072, price is now $1,321 per person
$1,321
per person
found 1 day ago

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,654 reviews)

Nov 6 - Nov 9

3 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,951, price is now $2,004 per person
$2,004
per person
found 1 day ago
This is a premium hotel. Great restaurant and spa was incredible . A plus location great room

Reviewed on Oct 6, 2026

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Surfside first class flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,008 reviews)

Nov 7 - Nov 10

3 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Price was $1,397, price is now $1,068 per person
$1,068
per person
found 1 day ago

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,654 reviews)

Nov 7 - Nov 10

3 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Price was $3,151, price is now $2,378 per person
$2,378
per person
found 1 day ago
This is a premium hotel. Great restaurant and spa was incredible . A plus location great room

Reviewed on Oct 6, 2026

The Shelborne By Proper, a Member of Design Hotels
4.5-star property

The Shelborne By Proper, a Member of Design Hotels

9.4/10 Exceptional! (225 reviews)

Nov 7 - Nov 10

3 night stay

Chicago (CHI) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Price was $2,367, price is now $1,814 per person
$1,814
per person
found 1 day ago

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