$25 Cheap flight deals from Chicago (CHI) to Boca Raton (FLL)
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This Weekend's Flight Deals from Chicago to Boca Raton
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.
FLL
Fort Lauderdale - Hollywood Intl.
$77 Roundtrip, found 3 hours ago
$77
Roundtrip
found 3 hours ago
MDW
Midway Intl.
PBI
Palm Beach Intl.
$249 Roundtrip, found 2 days ago
$249
Roundtrip
found 2 days ago
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$265 Roundtrip, found 8 hours ago
$265
Roundtrip
found 8 hours ago
RFD
Greater Rockford
FLL
Fort Lauderdale - Hollywood Intl.
$296 Roundtrip, found 1 day ago
$296
Roundtrip
found 1 day ago
Airfares from $25 One Way, $50 Round Trip from Chicago to Boca Raton
Prices starting at $50 for return flights and $25 for one-way flights to Boca Raton 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
$50 Roundtrip, found 4 hours ago
$50
Roundtrip
found 4 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$61 Roundtrip, found 1 day ago
$61
Roundtrip
found 1 day ago
ORD
Chicago
PBI
West Palm Beach
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
MDW
Chicago
FLL
Fort Lauderdale
$131 Roundtrip, found 12 hours ago
$131
Roundtrip
found 12 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$131 Roundtrip, found 3 hours ago
$131
Roundtrip
found 3 hours ago
Boca Raton economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Mar 13 - Mar 16
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Coach
Price was $925, price is now $493 per person
$493
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 26 - Mar 30
4 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,333, price is now $698 per person
$698
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
Boca Raton packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Crowne Plaza Hotel Fort Lauderdale Airport/Cruiseport by IHG
8.6/10 Excellent! (3,106 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • PremiumEconomy
Miami (MIA) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $851, price is now $568 per person
$568
per person
found 1 day ago
Girl at front desk was outstanding!
Reviewed on Jan 4, 2026
2.5-star property
Holiday Inn Express & Suites Fort Lauderdale Airport South by IHG
8.6/10 Excellent! (3,255 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Fort Lauderdale (FLL)
American Airlines • PremiumEconomy
Fort Lauderdale (FLL) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $921, price is now $610 per person
$610
per person
found 1 day ago
Room was fine staff was friendly and helpful. The only problem was that one of the elevators was in such poor repair that we decided it was not safe for our use and we would send it away so we could use to other one.
Reviewed on Jan 29, 2026
3.5-star property
Flow Fort Lauderdale Hotel
9/10 Wonderful! (560 reviews)
Mar 11 - Mar 15
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • PremiumEconomy
Miami (MIA) to Chicago (CHI)
Spirit Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,235, price is now $846 per person
$846
per person
found 1 day ago
We lived everything about this property from the amenities to the food and entertainment options within walking distance.
Reviewed on Jan 13, 2025
Boca Raton first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
President Hotel
8.4/10 Very Good! (1,775 reviews)
Mar 10 - Mar 17
7 night stay
Chicago (CHI) to Miami (MIA)
Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,398, price is now $1,360 per person
$1,360
per person
found 9 hours ago
Best hotel on south beach.
Reviewed on Nov 21, 2025
4.0-star property
Park Central South Beach
8.6/10 Excellent! (385 reviews)
Mar 10 - Mar 17
7 night stay
Chicago (CHI) to Miami (MIA)
Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,950, price is now $1,679 per person
$1,679
per person
found 9 hours ago
There were quite a few issues — the bathroom door and the safe were broken, the beach chairs on the beach couldn’t be used, and we had to carry folding chairs and towels provided by the hotel down to the beach. There was also only one slow elevator, and even though we booked Park Central, we were actually put in the building next door.
Still, the staff were all friendly and helpful, the room was clean, and the breakfast was good.
Reviewed on Dec 23, 2025
3.5-star property
Cavalier Hotel South Beach
8.4/10 Very Good! (1,001 reviews)
Mar 10 - Mar 17
7 night stay
Chicago (CHI) to Miami (MIA)
Delta • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $2,443, price is now $1,409 per person
$1,409
per person
found 9 hours ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
More About Flying To Boca Raton from Chicago
Route Information for Flights from Chicago to Boca Raton
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | FLL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Boca Raton
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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.