$44 Cheap flight deals from Chicago (CHI) to Aventura (MIA)

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This Weekend's Flight Deals from Chicago to Aventura

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, Mar 28 - Fri, Apr 3
MDW
Midway Intl.
MIA
Miami Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Mar 28 from Midway Intl. to Miami Intl., returning Fri, Apr 3, priced at $217 just found
Sat, Mar 28 - Fri, Apr 3
ORD
O'Hare Intl.
MIA
Miami Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Mar 28 from O'Hare Intl. to Miami Intl., returning Fri, Apr 3, priced at $237 just found
Sun, Mar 29 - Fri, Apr 3
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$266 Roundtrip, found 3 hours ago
$266
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Mar 29 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Apr 3, priced at $266 found 3 hours ago
Sat, Mar 28 - Fri, Apr 3
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$266 Roundtrip, found 1 hour ago
$266
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Mar 28 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Apr 3, priced at $266 found 1 hour ago

Airfares from $44 One Way, $87 Round Trip from Chicago to Aventura

Prices starting at $87 for return flights and $44 for one-way flights to Aventura were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Apr 9 - Wed, Apr 15
ORD
Chicago
FLL
Fort Lauderdale
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Apr 9 from Chicago to Fort Lauderdale, returning Wed, Apr 15, priced at $87 just found
Mon, Apr 13 - Thu, Apr 16
ORD
Chicago
MIA
Miami
$88 Roundtrip, found 21 hours ago
$88
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Chicago to Miami, returning Thu, Apr 16, priced at $88 found 21 hours ago
Sat, Apr 4 - Fri, Apr 10
MDW
Chicago
MIA
Miami
$95 Roundtrip, found 2 days ago
$95
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Apr 4 from Chicago to Miami, returning Fri, Apr 10, priced at $95 found 2 days ago
Fri, Apr 17 - Sat, Apr 25
MDW
Chicago
FLL
Fort Lauderdale
$160 Roundtrip, found 3 hours ago
$160
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Apr 17 from Chicago to Fort Lauderdale, returning Sat, Apr 25, priced at $160 found 3 hours ago
Sat, Apr 25 - Tue, May 5
RFD
Rockford
MIA
Miami
$197 Roundtrip, just found
$197
Roundtrip
just found
Select American Airlines flight, departing Sat, Apr 25 from Rockford to Miami, returning Tue, May 5, priced at $197 just found

Aventura economy flight packages

Price found within the past 48 hours. Click for updated prices.
President Hotel Villa
3.5-star property

President Hotel Villa

8.2/10 Very Good! (1,003 reviews)

May 7 - May 10

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Coach

Miami (MIA) to Chicago (CHI)

Frontier Airlines • Coach
Price was $782, price is now $440 per person
$440
per person
found 1 day ago
Although we didn't take advantage of it enough the hotel served breakfast every morning. Front desk staff awesome and very accommodating. A few times we had minor issues in our room and front desk staff would have maintenance up to our room in a matter of minutes. Minor drawback. A lot of hotel staff seemed not to know how to speak english well but front desk would let maintenance know the exact problem we were having and when they would arrive to our room we didnt need to talk that much because front desk already gave them the run down. I think hotel is in the best section of south beach. Beach 1 block away and walgreens across the street.

Reviewed on Apr 11, 2025

Creekside Inn
2.5-star property

Creekside Inn

7.8/10 Good! (1,027 reviews)

May 14 - May 17

3 night stay

Chicago (CHI) to Miami (MIA)

Southwest Airlines • Non-stop • Coach

Miami (MIA) to Chicago (CHI)

Frontier Airlines • Non-stop • Coach
Price was $957, price is now $466 per person
$466
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

Palm Beach Shores Resort and Vacation Villas
4.0-star property

Palm Beach Shores Resort and Vacation Villas

8.2/10 Very Good! (577 reviews)

Apr 28 - May 5

7 night stay

Chicago (CHI) to Fort Lauderdale (FLL)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,192, price is now $1,226 per person
$1,226
per person
found 23 hours ago
Very clean facility. It shows a bit of aging but was very welcoming. The staff is excellent.

Reviewed on Nov 6, 2025

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Aventura packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Penguin Hotel
3.5-star property

The Penguin Hotel

8.2/10 Very Good! (1,725 reviews)

Apr 30 - May 3

3 night stay

Chicago (ORD) to Miami (MIA)

Spirit Airlines • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,136, price is now $722 per person
$722
per person
found 1 day ago
It was ok nothing fancy

Reviewed on Feb 9, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,464 reviews)

May 7 - May 10

3 night stay

Chicago (ORD) to Miami (MIA)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,300, price is now $1,542 per person
$1,542
per person
found 1 day ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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Aventura first class flight packages

Price found within the past 48 hours. Click for updated prices.
Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.4/10 Very Good! (7,943 reviews)

May 21 - May 24

3 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to Chicago (CHI)

Delta • FirstClass
Price was $1,782, price is now $1,511 per person
$1,511
per person
found 10 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

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,464 reviews)

May 21 - May 24

3 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to Chicago (CHI)

Delta • FirstClass
Price was $3,042, price is now $2,311 per person
$2,311
per person
found 10 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

The Shelborne By Proper, a Member of Design Hotels
4.0-star property

The Shelborne By Proper, a Member of Design Hotels

9.4/10 Exceptional! (140 reviews)

May 21 - May 24

3 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to Chicago (CHI)

Delta • FirstClass
Price was $2,104, price is now $1,727 per person
$1,727
per person
found 10 hours ago
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More About Flying To Aventura from Chicago

Route Information for Flights from Chicago to Aventura

Origin Airport IATA Code
CHI
Destination Airport IATA Code
MIA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Aventura

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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.