$40 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.
$257 Roundtrip, just found
$257
Roundtrip
just found
ORD
O'Hare Intl.
PBI
Palm Beach Intl.
$412 Roundtrip, found 16 hours ago
$412
Roundtrip
found 16 hours ago
MDW
Midway Intl.
PBI
Palm Beach Intl.
$422 Roundtrip, found 16 hours ago
$422
Roundtrip
found 16 hours ago
RFD
Greater Rockford
PBI
Palm Beach Intl.
$491 Roundtrip, found 16 hours ago
$491
Roundtrip
found 16 hours ago
Airfares from $40 One Way, $80 Round Trip from Chicago to Boca Raton
Prices starting at $80 for return flights and $40 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
$80 Roundtrip, found 3 days ago
$80
Roundtrip
found 3 days ago
ORD
Chicago
FLL
Fort Lauderdale
$80 Roundtrip, found 14 hours ago
$80
Roundtrip
found 14 hours ago
MDW
Chicago
FLL
Fort Lauderdale
$200 Roundtrip, found 11 hours ago
$200
Roundtrip
found 11 hours ago
MDW
Chicago
FLL
Fort Lauderdale
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
ORD
Chicago
FLL
Fort Lauderdale
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Boca Raton economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Creekside Inn
7.8/10 Good! (1,027 reviews)
May 8 - May 12
4 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $1,290, price is now $573 per person
$573
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
3.0-star property
Casablanca Miami Beach
5.8/10 (321 reviews)
Apr 30 - May 3
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Coach
Miami (MIA) to Chicago (ORD)
Spirit Airlines • Coach
Price was $2,975, price is now $1,406 per person
$1,406
per person
found 3 hours ago
Very good for the price, Right on the beach, has a kitchen, Ocean view. Very easy check-in check-out. 1 -1/2 Block from Publix supermarket. 30 minutes from Miami International Airport. Will come again.
Reviewed on Apr 8, 2025
Boca Raton packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Kompose Boutique Hotel Miami Airport
9/10 Wonderful! (2,900 reviews)
Apr 23 - Apr 27
4 night stay
Chicago (ORD) to Miami (MIA)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,261, price is now $1,020 per person
$1,020
per person
found 12 hours ago
Excellent stay. Seamless check-in and room was perfect for my needs.
Reviewed on Feb 23, 2026
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,464 reviews)
Apr 23 - Apr 27
4 night stay
Chicago (ORD) to Miami (MIA)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,007, price is now $2,890 per person
$2,890
per person
found 12 hours ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
4.5-star property
Fontainebleau Miami Beach
8.4/10 Very Good! (7,943 reviews)
Apr 23 - Apr 27
4 night stay
Chicago (ORD) to Miami (MIA)
Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,776, price is now $2,109 per person
$2,109
per person
found 12 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
Boca Raton first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Solé Miami, A Noble House Resort
8.6/10 Excellent! (2,063 reviews)
Apr 24 - Apr 28
4 night stay
Chicago (CHI) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (CHI)
Spirit Airlines • FirstClass
Price was $1,360, price is now $1,039 per person
$1,039
per person
found 1 day ago
Everything was just great.
Reviewed on Dec 27, 2025
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,464 reviews)
Apr 24 - Apr 28
4 night stay
Chicago (CHI) to Miami (MIA)
United • FirstClass
Miami (MIA) to Chicago (CHI)
Spirit Airlines • FirstClass
Save 100% on your flight
Price was $3,800, price is now $2,754 per person
$2,754
per person
found 1 day ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 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.