$29 Cheap flight deals from Chicago (CHI) to Pembroke Pines (FLL)

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This Weekend's Flight Deals from Chicago to Pembroke Pines

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, May 17 - Wed, May 20
MDW
Midway Intl.
MIA
Miami Intl.
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, May 17 from Midway Intl. to Miami Intl., returning Wed, May 20, priced at $205 found 5 days ago
Sun, May 17 - Thu, May 28
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$280 Roundtrip, found 16 hours ago
$280
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sun, May 17 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, May 28, priced at $280 found 16 hours ago
Sun, May 17 - Sun, May 24
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$307 Roundtrip, found 1 hour ago
$307
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, May 17 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sun, May 24, priced at $307 found 1 hour ago
Sun, May 17 - Thu, May 28
RFD
Greater Rockford
FLL
Fort Lauderdale - Hollywood Intl.
$350 Roundtrip, found 16 hours ago
$350
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sun, May 17 from Greater Rockford to Fort Lauderdale - Hollywood Intl., returning Thu, May 28, priced at $350 found 16 hours ago

Airfares from $29 One Way, $56 Round Trip from Chicago to Pembroke Pines

Prices starting at $56 for return flights and $29 for one-way flights to Pembroke Pines were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 19 - Wed, Aug 26
ORD
Chicago
FLL
Fort Lauderdale
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Chicago to Fort Lauderdale, returning Wed, Aug 26, priced at $56 found 1 hour ago
Wed, May 20 - Thu, May 28
ORD
Chicago
FLL
Fort Lauderdale
$105 Roundtrip, found 6 days ago
$105
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, May 20 from Chicago to Fort Lauderdale, returning Thu, May 28, priced at $105 found 6 days ago
Tue, Aug 4 - Tue, Aug 11
ORD
Chicago
FLL
Fort Lauderdale
$169 Roundtrip, found 6 hours ago
$169
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Aug 4 from Chicago to Fort Lauderdale, returning Tue, Aug 11, priced at $169 found 6 hours ago
Tue, Jun 16 - Tue, Jul 7
ORD
Chicago
FLL
Fort Lauderdale
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 16 from Chicago to Fort Lauderdale, returning Tue, Jul 7, priced at $173 found 1 day ago
Tue, May 26 - Tue, Jun 2
MDW
Chicago
FLL
Fort Lauderdale
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 26 from Chicago to Fort Lauderdale, returning Tue, Jun 2, priced at $185 found 3 days ago

Pembroke Pines economy flight packages

Price found within the past 48 hours. Click for updated prices.
Brickell Bay 3304
3.0-star property

Brickell Bay 3304

No reviews

Jun 19 - Jun 22

3 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,414, price is now $732 per person
$732
per person
found 1 day ago
The W - Bayshore Unit 1003
3.0-star property

The W - Bayshore Unit 1003

6/10 (2 reviews)

Jun 18 - Jun 22

4 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Chicago (CHI)

Southwest Airlines • Coach
Price was $2,732, price is now $772 per person
$772
per person
found 1 day ago
Creekside Inn
2.5-star property

Creekside Inn

7.8/10 Good! (1,010 reviews)

Jun 25 - Jun 30

5 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,675, price is now $863 per person
$863
per person
found 1 day ago
Leaving a review to let Travellers know that this place deserves a better rating and reviews than what some Travellers have left. We had a great stay! The property is older and could use some upgrades but it was exactly suited for our stay. Property is right on a canal where you can see Tarpon, Manatees and other fish, if you have a boat you can dock right there. Our stay was quiet and peaceful and housekeeping took care of any needs we had. Its within walking distance of a few restaurants, dive shop, bait shop, snorkel tour. I would recommend Lido73, Mar Bar and Old Tavernier restaurants all within walking distance. Just know it not the 4 seasons just and older property that will suit your needs. I would definitely come stay again.

Reviewed on Mar 22, 2026

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Pembroke Pines packages with premium economy flights

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

President Hotel

8.4/10 Very Good! (2,302 reviews)

Jun 16 - Jun 20

4 night stay

Chicago (ORD) to Miami (MIA)

United • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,323, price is now $913 per person
$913
per person
found 17 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

Marenas Beach Resort
4.0-star property

Marenas Beach Resort

8.6/10 Excellent! (1,005 reviews)

Jun 16 - Jun 20

4 night stay

Chicago (ORD) to Miami (MIA)

United • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,553, price is now $1,150 per person
$1,150
per person
found 17 hours ago
great location, easy registration, and very clean

Reviewed on Mar 15, 2025

Kimpton EPIC Hotel by IHG
5.0-star property

Kimpton EPIC Hotel by IHG

9/10 Wonderful! (2,450 reviews)

Jun 16 - Jun 20

4 night stay

Chicago (ORD) to Miami (MIA)

United • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,553, price is now $1,151 per person
$1,151
per person
found 17 hours ago
A great place to stay if you have to spend some time in Brickell

Reviewed on Apr 29, 2026

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Pembroke Pines business class flight packages

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
4.0-star property

Pelican Hotel

9.2/10 Wonderful! (457 reviews)

Jun 9 - Jun 13

4 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,260, price is now $877 per person
$877
per person
found 3 hours ago
My recent stay at the Pelican Hotel was nothing short of delightful. The location is truly exceptional — perfectly situated to enjoy the very best of the area. From the moment I arrived, the warm and friendly atmosphere made me feel completely at ease. The service was impeccable. Both room service and management were consistently professional and courteous, with special appreciation to Oscar, whose attentiveness and genuine hospitality made a lasting impression. The dining experience was outstanding. Every meal was a pleasure, but the fried octopus deserves special mention — perfectly prepared and absolutely unforgettable. The rooms themselves were a highlight: comfortable, thoughtfully appointed, and each with its own unique design that adds charm and character to the stay. The complimentary cocktails were another memorable touch — expertly made and thoroughly enjoyable. Overall, my time at the Pelican Hotel was a wonderful experience from start to finish. I look forward to returning and will gladly book again without hesitation.

Reviewed on Aug 11, 2025

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,495 reviews)

Jun 9 - Jun 13

4 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,866, price is now $1,939 per person
$1,939
per person
found 3 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.4/10 Very Good! (8,133 reviews)

Jun 9 - Jun 13

4 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,414, price is now $1,019 per person
$1,019
per person
found 3 hours ago
Beautiful hotel! We did a last minute mother-daughter long weekend and it was perfect. Pool is busy but so pretty and plenty of space to swim around. Beach was well staffed and so easy to access. I loved the beach trail that goes all the way to south beach-great for morning walk!

Reviewed on Apr 28, 2026

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Pembroke Pines first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,141 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (CHI) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (CHI)

American Airlines • FirstClass
Price was $1,870, price is now $1,439 per person
$1,439
per person
found 23 hours ago
The hotel is clean. The staff will greet you but not immediately. The rooms are ok but the beds are small and everything is built for shorter stature people. I am average and the beds and toilet are short! TV's are older. Everything is average and ok.

Reviewed on Jan 19, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,495 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (CHI) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (CHI)

American Airlines • FirstClass
Price was $2,975, price is now $2,225 per person
$2,225
per person
found 23 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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

The Shelborne By Proper, a Member of Design Hotels

9.4/10 Exceptional! (168 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (CHI) to Miami (MIA)

United • FirstClass

Miami (MIA) to Chicago (CHI)

American Airlines • FirstClass
Price was $2,095, price is now $1,692 per person
$1,692
per person
found 23 hours ago
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More About Flying To Pembroke Pines from Chicago

Route Information for Flights from Chicago to Pembroke Pines

Origin Airport IATA Code
CHI
Destination Airport IATA Code
FLL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Pembroke Pines

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.