$33 Cheap flight deals from Chicago (CHI) to Cutler Bay (MIA)
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This Weekend's Flight Deals from Chicago to Cutler Bay
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.
$213 Roundtrip, just found
$213
Roundtrip
just found
MDW
Midway Intl.
MIA
Miami Intl.
$325 Roundtrip, just found
$325
Roundtrip
just found
RFD
Greater Rockford
MIA
Miami Intl.
$410 Roundtrip, found 3 days ago
$410
Roundtrip
found 3 days ago
Airfares from $33 One Way, $60 Round Trip from Chicago to Cutler Bay
Prices starting at $60 for return flights and $33 for one-way flights to Cutler Bay 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
$60 Roundtrip, found 19 hours ago
$60
Roundtrip
found 19 hours ago
ORD
Chicago
MIA
Miami
$63 Roundtrip, found 9 hours ago
$63
Roundtrip
found 9 hours ago
ORD
Chicago
MIA
Miami
$71 Roundtrip, found 3 days ago
$71
Roundtrip
found 3 days ago
ORD
Chicago
MIA
Miami
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
ORD
Chicago
MIA
Miami
$94 Roundtrip, found 9 hours ago
$94
Roundtrip
found 9 hours ago
Cutler Bay economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Creekside Inn
7.8/10 Good! (1,002 reviews)
May 29 - Jun 2
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,371, price is now $716 per person
$716
per person
found 1 day ago
Leaving a review to let Travellers know that this place deserves a better rating and reviews than what some Travellers have left. We had a great stay! The property is older and could use some upgrades but it was exactly suited for our stay. Property is right on a canal where you can see Tarpon, Manatees and other fish, if you have a boat you can dock right there. Our stay was quiet and peaceful and housekeeping took care of any needs we had. Its within walking distance of a few restaurants, dive shop, bait shop, snorkel tour. I would recommend Lido73, Mar Bar and Old Tavernier restaurants all within walking distance. Just know it not the 4 seasons just and older property that will suit your needs. I would definitely come stay again.
Reviewed on Mar 22, 2026
3.0-star property
Casablanca Miami Beach
5.8/10 (322 reviews)
May 29 - Jun 2
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • Roundtrip • Coach
Price was $2,089, price is now $1,040 per person
$1,040
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
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
May 19 - May 24
5 night stay
Chicago (CHI) to Miami (MIA)
Frontier Airlines • Non-stop • Coach
Miami (MIA) to Chicago (CHI)
Spirit Airlines • Non-stop • Coach
Price was $18,703, price is now $9,824 per person
$9,824
per person
found 1 day ago
Cutler Bay packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Pelican Hotel
9.2/10 Wonderful! (443 reviews)
May 14 - May 18
4 night stay
Chicago (ORD) to Miami (MIA)
Spirit Airlines • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Frontier Airlines • PremiumEconomy
Price was $1,188, price is now $807 per person
$807
per person
found 14 hours ago
My recent stay at the Pelican Hotel was nothing short of delightful. The location is truly exceptional — perfectly situated to enjoy the very best of the area. From the moment I arrived, the warm and friendly atmosphere made me feel completely at ease.
The service was impeccable. Both room service and management were consistently professional and courteous, with special appreciation to Oscar, whose attentiveness and genuine hospitality made a lasting impression.
The dining experience was outstanding. Every meal was a pleasure, but the fried octopus deserves special mention — perfectly prepared and absolutely unforgettable.
The rooms themselves were a highlight: comfortable, thoughtfully appointed, and each with its own unique design that adds charm and character to the stay. The complimentary cocktails were another memorable touch — expertly made and thoroughly enjoyable.
Overall, my time at the Pelican Hotel was a wonderful experience from start to finish. I look forward to returning and will gladly book again without hesitation.
Reviewed on Aug 11, 2025
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
May 14 - May 18
4 night stay
Chicago (ORD) to Miami (MIA)
Spirit Airlines • PremiumEconomy
Miami (MIA) to Chicago (ORD)
Frontier Airlines • PremiumEconomy
Price was $15,399, price is now $8,672 per person
$8,672
per person
found 14 hours ago
3.5-star property
Cavalier Hotel South Beach
8.6/10 Excellent! (1,000 reviews)
May 22 - May 25
3 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,421, price is now $949 per person
$949
per person
found 24 hours ago
Staff was great, elevator is tired, but I loved the proximity to everything
Reviewed on Jan 3, 2026
Cutler Bay business class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Silver Spray Motel
6.8/10 (777 reviews)
May 14 - May 18
4 night stay
Chicago (ORD) to Miami (MIA)
Frontier Airlines • Roundtrip • BusinessClass
Price was $829, price is now $672 per person
$672
per person
found 1 day ago
The front desk guy is super nice, he is really helpful
Reviewed on May 20, 2024
Cutler Bay first class flight packages
Price found within the past 48 hours. Click for updated prices.
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
8/10 Very Good! (1 review)
May 14 - May 18
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (CHI)
United • FirstClass
Price was $16,330, price is now $8,732 per person
$8,732
per person
found 1 day ago
5.0-star property
1 Hotel South Beach
9.4/10 Exceptional! (1,471 reviews)
May 14 - May 18
4 night stay
Chicago (CHI) to Miami (MIA)
American Airlines • FirstClass
Miami (MIA) to Chicago (CHI)
United • FirstClass
Price was $3,451, price is now $2,428 per person
$2,428
per person
found 1 day ago
The best hotel I have ever stayed in!
Reviewed on Jan 17, 2026
More About Flying To Cutler Bay from Chicago
Route Information for Flights from Chicago to Cutler Bay
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | MIA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Cutler Bay
Great Deals on Flights From Chicago to Cutler Bay
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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.