$26 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.
ORD
O'Hare Intl.
MIA
Miami Intl.
$89 Roundtrip, found 1 hour ago
$89
Roundtrip
found 1 hour ago
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$91 Roundtrip, found 2 hours ago
$91
Roundtrip
found 2 hours ago
MDW
Midway Intl.
MIA
Miami Intl.
$259 Roundtrip, found 23 hours ago
$259
Roundtrip
found 23 hours ago
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Airfares from $26 One Way, $50 Round Trip from Chicago to Hollywood
Prices starting at $50 for return flights and $26 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
MIA
Miami
$50 Roundtrip, found 18 hours ago
$50
Roundtrip
found 18 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$50 Roundtrip, found 10 hours ago
$50
Roundtrip
found 10 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$57 Roundtrip, found 16 hours ago
$57
Roundtrip
found 16 hours ago
MDW
Chicago
MIA
Miami
$60 Roundtrip, found 1 hour ago
$60
Roundtrip
found 1 hour ago
MDW
Chicago
FLL
Fort Lauderdale
$130 Roundtrip, found 15 hours ago
$130
Roundtrip
found 15 hours ago
Hollywood economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Hyatt Place Miami Airport-East
8.2/10 Very Good! (2,247 reviews)
Mar 24 - Mar 27
3 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $719, price is now $325 per person
$325
per person
found 1 day ago
Room was cleaned and staff were very pleasant.
Reviewed on Feb 3, 2026
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Mar 6 - Mar 10
4 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Coach
Price was $1,331, price is now $657 per person
$657
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
2.5-star property
Creekside Inn
8/10 Very Good! (1,004 reviews)
Mar 29 - Apr 3
5 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Coach
Miami (MIA) to Chicago (CHI)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,714, price is now $918 per person
$918
per person
found 1 day ago
I only stayed one night but overall, Creekside was better than I was expecting. For an old keys motel type inn, it was very clean and well kept.
Reviewed on Aug 2, 2025
Hollywood packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Fontainebleau Miami Beach
8.2/10 Very Good! (7,303 reviews)
Mar 22 - Mar 25
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Spirit Airlines • PremiumEconomy
Price was $1,745, price is now $1,360 per person
$1,360
per person
found 18 hours ago
The hotel is wonderful, but the elevators suck.
The next time I stay there, I’m going to complain about the elevators
Great hotel absolutely wonderful I’m not sure I’d stay there again without an ass Assurance at the elevators work
Reviewed on Jan 28, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,365 reviews)
Mar 22 - Mar 25
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $2,955, price is now $2,045 per person
$2,045
per person
found 18 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! (56 reviews)
Mar 22 - Mar 25
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Spirit Airlines • PremiumEconomy
Price was $1,874, price is now $1,361 per person
$1,361
per person
found 18 hours ago
Hollywood first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Sugarloaf Key Hotel at KOA Resort
9.8/10 Exceptional! (456 reviews)
Mar 28 - Apr 1
4 night stay
Chicago (CHI) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (CHI)
American Airlines • FirstClass
Price was $2,094, price is now $1,766 per person
$1,766
per person
found 2 hours ago
Great campground with vacation rental access. Water sport activities for rent and a short drive to key west. Camp store and pub on site as well!
Reviewed on Mar 27, 2025
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,365 reviews)
Mar 25 - Mar 30
5 night stay
Chicago (MDW) to Miami (MIA)
Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $6,278, price is now $3,892 per person
$3,892
per person
found 1 day ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 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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- Things to do in Hallandale Beach
- 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
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- Flights from Kansas City (MCI) to Fort Lauderdale (FLL)
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- Flights from Portland (PDX) to Fort Lauderdale (FLL)
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- Flights from Port of Spain (POS) to Fort Lauderdale (FLL)
- Flights from Providence (PVD) to Fort Lauderdale (FLL)
- Flights from Raleigh (RDU) to Fort Lauderdale (FLL)
- Flights from Richmond (RIC) to Fort Lauderdale (FLL)
- Flights from Fort Myers (RSW) to Fort Lauderdale (FLL)
- Flights from Santo Domingo (SDQ) to Fort Lauderdale (FLL)
- Flights from Seattle (SEA) to Fort Lauderdale (FLL)
- Flights from San Francisco (SFO) to Fort Lauderdale (FLL)
- Flights from Sarasota (SRQ) to Fort Lauderdale (FLL)
- Flights from Santiago (STI) to Fort Lauderdale (FLL)
- Flights from St. Louis (STL) to Fort Lauderdale (FLL)
- Flights from Syracuse (SYR) to Fort Lauderdale (FLL)
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- Flights from Tampa (TPA) to Fort Lauderdale (FLL)
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- Flights from Boston to Miami
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- Flights from New York to Miami
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- Things to do in Hallandale Beach
- 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.