$31 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.

Sat, Apr 4 - Fri, Apr 10
MDW
Midway Intl.
MIA
Miami Intl.
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Midway Intl. to Miami Intl., returning Fri, Apr 10, priced at $117 found 9 hours ago
Sat, Apr 4 - Sat, Apr 11
ORD
O'Hare Intl.
MIA
Miami Intl.
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Apr 4 from O'Hare Intl. to Miami Intl., returning Sat, Apr 11, priced at $132 found 1 hour ago

Airfares from $31 One Way, $62 Round Trip from Chicago to Cutler Bay

Prices starting at $62 for return flights and $31 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.

Mon, Apr 13 - Thu, Apr 16
ORD
Chicago
MIA
Miami
$62 Roundtrip, just found
$62
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Apr 13 from Chicago to Miami, returning Thu, Apr 16, priced at $62 just found
Tue, Apr 14 - Thu, Apr 16
ORD
Chicago
MIA
Miami
$62 Roundtrip, found 5 hours ago
$62
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, Apr 14 from Chicago to Miami, returning Thu, Apr 16, priced at $62 found 5 hours ago
Mon, Apr 13 - Thu, Apr 16
ORD
Chicago
MIA
Miami
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Apr 13 from Chicago to Miami, returning Thu, Apr 16, priced at $68 just found
Mon, Apr 6 - Fri, Apr 10
MDW
Chicago
MIA
Miami
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Apr 6 from Chicago to Miami, returning Fri, Apr 10, priced at $108 found 6 days ago
Sat, Apr 25 - Tue, May 5
RFD
Rockford
MIA
Miami
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Apr 25 from Rockford to Miami, returning Tue, May 5, priced at $197 found 3 days ago

Cutler Bay economy flight packages

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
2.5-star property

Creekside Inn

7.8/10 Good! (1,027 reviews)

May 4 - May 8

4 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,220, price is now $558 per person
$558
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

Casa Boutique Hotel
3.0-star property

Casa Boutique Hotel

8.4/10 Very Good! (1,000 reviews)

May 6 - May 13

7 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,097, price is now $620 per person
$620
per person
found 8 hours ago
Euro style, small hotel, restaurant on first floor $$$. Overall good, clean and comfy beds. Humidity damage to the finishes, Floring looks not clean. Coffee, water, beach towels at front desk. Friendly stuff. Parking at ramp, 3min walk, about $1/hr. At the street meter $6/hr.

Reviewed on Dec 28, 2025

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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

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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.