$42 Cheap flight deals from Chicago (CHI) to Hollywood (FLL)
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This Weekend's Flight Deals from Chicago to Hollywood
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.
$301 Roundtrip, just found
$301
Roundtrip
just found
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$324 Roundtrip, just found
$324
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$366 Roundtrip, found 1 hour ago
$366
Roundtrip
found 1 hour ago
RFD
Greater Rockford
MIA
Miami Intl.
$449 Roundtrip, found 6 days ago
$449
Roundtrip
found 6 days ago
Airfares from $42 One Way, $82 Round Trip from Chicago to Hollywood
Prices starting at $82 for return flights and $42 for one-way flights to Hollywood 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
$82 Roundtrip, just found
$82
Roundtrip
just found
ORD
Chicago
MIA
Miami
$171 Roundtrip, just found
$171
Roundtrip
just found
ORD
Chicago
FLL
Fort Lauderdale
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
ORD
Chicago
FLL
Fort Lauderdale
$171 Roundtrip, just found
$171
Roundtrip
just found
RFD
Rockford
MIA
Miami
$175 Roundtrip, found 1 hour ago
$175
Roundtrip
found 1 hour ago
Hollywood economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Local House
9.2/10 Wonderful! (1,004 reviews)
Jul 23 - Jul 31
8 night stay
Chicago (CHI) to Miami (MIA)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,864, price is now $1,062 per person
$1,062
per person
found 24 hours ago
We were thrilled with the property itself, location and such helpful and warm staff! The food at their restaurant was fresh and superb!
Reviewed on Mar 6, 2026
Hollywood packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Cavalier Hotel South Beach
8.6/10 Excellent! (1,002 reviews)
Aug 7 - Aug 10
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $916, price is now $609 per person
$609
per person
found 19 hours ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
4.5-star property
Fontainebleau Miami Beach
8.4/10 Very Good! (8,366 reviews)
Aug 7 - Aug 10
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,020, price is now $726 per person
$726
per person
found 19 hours ago
Overall experience was great! However, they need to fire the current house keeping. They’re lazy and you walk into a dirty room with stains and hair everywhere . Thank God they upgraded me to a one bedroom suite which made me give them a 5 star. There were dozens of people complaining of dirty rooms. Fire management if they cannot hire quality housekeepers.
Reviewed on Jun 2, 2026
4.0-star property
Pelican Hotel
9.2/10 Wonderful! (475 reviews)
Aug 7 - Aug 10
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $947, price is now $679 per person
$679
per person
found 19 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
More About Flying To Hollywood from Chicago
Route Information for Flights from Chicago to Hollywood
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | FLL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Hollywood
Looking for cheap Chicago to Hollywood flights? Orbitz has the cheapest air fares for flights from Chicago to Hollywood. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.
Mobile Deals and Steals
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Cheap Air Ticket Prices Guaranteed
Orbitz is your number one source for low fares for Chicago to Hollywood flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Hollywood. Need hotels too? You can book them last minute on your mobile phone.
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- Car rentals in Hallandale Beach
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.