$52 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.
$248 Roundtrip, found 3 days ago
$248
Roundtrip
found 3 days ago
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$254 Roundtrip, found 1 hour ago
$254
Roundtrip
found 1 hour ago
MDW
Midway Intl.
MIA
Miami Intl.
$262 Roundtrip, just found
$262
Roundtrip
just found
ORD
O'Hare Intl.
MIA
Miami Intl.
$378 Roundtrip, found 17 hours ago
$378
Roundtrip
found 17 hours ago
Airfares from $52 One Way, $105 Round Trip from Chicago to Hollywood
Prices starting at $105 for return flights and $52 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
$105 Roundtrip, found 2 days ago
$105
Roundtrip
found 2 days ago
ORD
Chicago
FLL
Fort Lauderdale
$175 Roundtrip, found 19 hours ago
$175
Roundtrip
found 19 hours ago
MDW
Chicago
FLL
Fort Lauderdale
$184 Roundtrip, found 19 hours ago
$184
Roundtrip
found 19 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$189 Roundtrip, found 2 hours ago
$189
Roundtrip
found 2 hours ago
MDW
Chicago
MIA
Miami
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Hollywood economy flight packages
Price found within the past 48 hours. Click for updated prices.
Hollywood packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Riverside Hotel
9/10 Wonderful! (2,966 reviews)
Jun 28 - Jul 3
5 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,168, price is now $818 per person
$818
per person
found 1 day ago
Beautiful view, large room, great venue, wonderful staff!
Reviewed on Apr 15, 2026
4.0-star property
Pelican Grand Beach Resort - A Noble House Resort
8.8/10 Excellent! (1,539 reviews)
Jun 28 - Jul 3
5 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,248, price is now $881 per person
$881
per person
found 1 day ago
This is the 4th year my spouse and I have visited. We love location (2.5 miles from local idiots at Beachplace area hotels), beach access, and spacious suites.
Over time, we dine there less and less. Prices are high, and the quality of the food doesn't support the price.
One thing I noticed on this trip was tighter control on towels and pool area seats. I asked for that because last year it seemed like a third to half of people occupying pool area seats were not staying at the hotel. They bragged and laughed about it. This time, the paying guests and their families could get seats this time. I appreciate the actions taken.
Less positive - improved elevator service has been promised for at least 4 years. One guest elevator was out of service for our entire, 4 night stay. I have to give that a "Really?"
Notes for first time guests - When adjusting lights and fans, it's not you. I think that's how those appliances are configured in Scandanavia. Also, consider using bath clogs. The walls, flooring, and soaps in the guest room bathrooms are a recipe for a cracked skull.
Love the place. Will come back.
Reviewed on May 22, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,511 reviews)
Jun 28 - Jul 3
5 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,516, price is now $2,515 per person
$2,515
per person
found 1 day ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
Hollywood first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Eden Roc Miami Beach
8.6/10 Excellent! (3,230 reviews)
Jun 24 - Jun 26
2 night stay
Chicago (ORD) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (ORD)
United • FirstClass
Price was $1,538, price is now $1,267 per person
$1,267
per person
found 1 day ago
Very communicative hotel. Super friendly and professional
Reviewed on Mar 8, 2026
4.5-star property
Fontainebleau Miami Beach
8.4/10 Very Good! (8,206 reviews)
Jun 24 - Jun 26
2 night stay
Chicago (ORD) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (ORD)
United • FirstClass
Price was $1,805, price is now $1,498 per person
$1,498
per person
found 1 day ago
My stay was everything I could dream of. The staff were so friendly and welcoming. The hotel was so clean. I will most definitely be back. Thank you Fontainebleau!
Reviewed on May 19, 2026
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
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- Hotels in Miami
- Visit Gulfstream Park Racing and Casino
- Car rentals in Fort Lauderdale
- Hotels in Fort Lauderdale
- Hotels in Hallandale Beach
- Cheap Hotels in Hallandale Beach
- Flights to Miami
- Car rentals at Fort Lauderdale Airport (FLL)
- Flights to Fort Lauderdale
- Hallandale Beach vacation rentals
- Hotels near Hollywood Sheridan Street Station
- 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.