$29 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.
MIA
Miami Intl.
$357 Roundtrip, found 13 hours ago
$357
Roundtrip
found 13 hours ago
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$366 Roundtrip, found 2 hours ago
$366
Roundtrip
found 2 hours ago
ORD
O'Hare Intl.
MIA
Miami Intl.
$424 Roundtrip, just found
$424
Roundtrip
just found
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$441 Roundtrip, found 1 day ago
$441
Roundtrip
found 1 day ago
Airfares from $29 One Way, $56 Round Trip from Chicago to Hollywood
Prices starting at $56 for return flights and $29 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
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
ORD
Chicago
FLL
Fort Lauderdale
$105 Roundtrip, found 5 days ago
$105
Roundtrip
found 5 days ago
ORD
Chicago
FLL
Fort Lauderdale
$173 Roundtrip, found 20 hours ago
$173
Roundtrip
found 20 hours ago
MDW
Chicago
FLL
Fort Lauderdale
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
MDW
Chicago
FLL
Fort Lauderdale
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 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
President Hotel
8.4/10 Very Good! (2,272 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 2 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
4.0-star property
Marenas Beach Resort
8.6/10 Excellent! (1,000 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 2 hours ago
great location, easy registration, and very clean
Reviewed on Mar 15, 2025
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 2 hours ago
A great place to stay if you have to spend some time in Brickell
Reviewed on Apr 29, 2026
Hollywood first class flight packages
Price found within the past 48 hours. Click for updated prices.
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 9 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
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 9 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! (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 9 hours ago
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
Great Deals on Flights From Chicago to Hollywood
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Flights That Fit Your Budget
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Flights from Chicago
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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
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- 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 Charleston (CHS) to Fort Lauderdale (FLL)
- Flights from Charlotte (CLT) to Fort Lauderdale (FLL)
- Flights from Columbus (CMH) to Fort Lauderdale (FLL)
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- Flights from New York (JFK) to Fort Lauderdale (FLL)
- Flights from Kingston (KIN) to Fort Lauderdale (FLL)
- Flights from Los Angeles (LAX) to Fort Lauderdale (FLL)
- Flights from New York (LGA) to Fort Lauderdale (FLL)
- Flights from Montego Bay (MBJ) to Fort Lauderdale (FLL)
- Flights from Kansas City (MCI) to Fort Lauderdale (FLL)
- Flights from Memphis (MEM) to Fort Lauderdale (FLL)
- Flights from Minneapolis (MSP) to Fort Lauderdale (FLL)
- Flights from New Orleans (MSY) to Fort Lauderdale (FLL)
- Flights from Chicago (ORD) to Fort Lauderdale (FLL)
- Flights from Norfolk (ORF) to Fort Lauderdale (FLL)
- Flights from Port-au-Prince (PAP) to Fort Lauderdale (FLL)
- Flights from Portland (PDX) to Fort Lauderdale (FLL)
- Flights from Phoenix (PHX) to Fort Lauderdale (FLL)
- Flights from St. Petersburg (PIE) to Fort Lauderdale (FLL)
- Flights from Pittsburgh (PIT) 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)
- Flights from Tallahassee (TLH) to Fort Lauderdale (FLL)
- Flights from Tampa (TPA) to Fort Lauderdale (FLL)
- Flights from Boston to Hallandale Beach
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- Flights from Boston to Miami
- Flights from Chicago to Miami
- 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.