$25 Cheap flight deals from Chicago (CHI) to Weston (FLL)
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This Weekend's Flight Deals from Chicago to Weston
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.
$87 Roundtrip, just found
$87
Roundtrip
just found
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$234 Roundtrip, found 16 hours ago
$234
Roundtrip
found 16 hours ago
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$265 Roundtrip, found 19 hours ago
$265
Roundtrip
found 19 hours ago
Airfares from $25 One Way, $51 Round Trip from Chicago to Weston
Prices starting at $51 for return flights and $25 for one-way flights to Weston 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
$51 Roundtrip, found 2 hours ago
$51
Roundtrip
found 2 hours ago
ORD
Chicago
FLL
Fort Lauderdale
$51 Roundtrip, found 1 hour ago
$51
Roundtrip
found 1 hour ago
ORD
Chicago
FLL
Fort Lauderdale
$58 Roundtrip, just found
$58
Roundtrip
just found
MDW
Chicago
MIA
Miami
$63 Roundtrip, found 2 hours ago
$63
Roundtrip
found 2 hours ago
MDW
Chicago
FLL
Fort Lauderdale
$128 Roundtrip, found 5 days ago
$128
Roundtrip
found 5 days ago
Weston economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Casablanca Miami Beach
5.8/10 (311 reviews)
Mar 4 - Mar 7
3 night stay
Chicago (CHI) to Miami (MIA)
Spirit Airlines • Roundtrip • Coach
Price was $725, price is now $388 per person
$388
per person
found 1 day 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
2.5-star property
Creekside Inn
8/10 Very Good! (1,004 reviews)
Mar 27 - Mar 30
3 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,015, price is now $509 per person
$509
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
5.0-star property
Amrit Ocean Resort and Residences - Singer Island
8.8/10 Excellent! (188 reviews)
Mar 19 - Mar 24
5 night stay
Chicago (CHI) to Fort Lauderdale (FLL)
Frontier Airlines • Coach
Fort Lauderdale (FLL) to Chicago (CHI)
Spirit Airlines • Coach
Price was $2,672, price is now $1,426 per person
$1,426
per person
found 1 day ago
From check-in to check-out, everyone was helpful and efficient. Ricardo provided us with all the information we needed and showed us around the hotel. The tiki bar at the entrance to the beach was a great perk. Resort was clean, room was spacious and bed comfortable. Chase greeted us at the beach each morning and set us up with chairs, umbrella and towels. We also enjoyed the pool; very comfortable pool chairs. All around great experience at Amrit. Will definitely return.
Reviewed on Jul 10, 2025
Weston 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
just found
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
just found
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
just found
We lived everything about this property from the amenities to the food and entertainment options within walking distance.
Reviewed on Jan 13, 2025
Weston first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Park Central South Beach
8.6/10 Excellent! (385 reviews)
Mar 21 - Mar 29
8 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,090, price is now $2,012 per person
$2,012
per person
found 1 day 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
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,365 reviews)
Mar 21 - Mar 29
8 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $8,990, price is now $5,181 per person
$5,181
per person
found 1 day ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
More About Flying To Weston from Chicago
Route Information for Flights from Chicago to Weston
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | FLL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Weston
Great Deals on Flights From Chicago to Weston
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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.