$43 Cheap flight deals from Chicago (CHI) to Sunny Isles Beach (MIA)

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This Weekend's Flight Deals from Chicago to Sunny Isles Beach

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, Jun 27 - Tue, Jun 30
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$291 Roundtrip, found 8 hours ago
$291
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jun 27 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Jun 30, priced at $291 found 8 hours ago
Sat, Jun 27 - Mon, Jun 29
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$350 Roundtrip, found 7 hours ago
$350
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Jun 27 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 29, priced at $350 found 7 hours ago
Sat, Jun 27 - Tue, Jun 30
RFD
Greater Rockford
MIA
Miami Intl.
$392 Roundtrip, found 15 hours ago
$392
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Sat, Jun 27 from Greater Rockford to Miami Intl., returning Tue, Jun 30, priced at $392 found 15 hours ago
Sat, Jun 27 - Sun, Jun 28
MDW
Midway Intl.
MIA
Miami Intl.
$438 Roundtrip, found 8 hours ago
$438
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jun 27 from Midway Intl. to Miami Intl., returning Sun, Jun 28, priced at $438 found 8 hours ago

Airfares from $43 One Way, $82 Round Trip from Chicago to Sunny Isles Beach

Prices starting at $82 for return flights and $43 for one-way flights to Sunny Isles Beach were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Aug 29 - Sat, Sep 5
ORD
Chicago
FLL
Fort Lauderdale
$82 Roundtrip, found 19 hours ago
$82
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Chicago to Fort Lauderdale, returning Sat, Sep 5, priced at $82 found 19 hours ago
Sat, Aug 1 - Sat, Aug 8
RFD
Rockford
MIA
Miami
$171 Roundtrip, found 22 hours ago
$171
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Aug 1 from Rockford to Miami, returning Sat, Aug 8, priced at $171 found 22 hours ago
Wed, Aug 5 - Tue, Aug 11
ORD
Chicago
MIA
Miami
$171 Roundtrip, just found
$171
Roundtrip
just found
Select American Airlines flight, departing Wed, Aug 5 from Chicago to Miami, returning Tue, Aug 11, priced at $171 just found
Sat, Sep 12 - Sat, Sep 19
MDW
Chicago
FLL
Fort Lauderdale
$171 Roundtrip, found 3 hours ago
$171
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Chicago to Fort Lauderdale, returning Sat, Sep 19, priced at $171 found 3 hours ago
Wed, Aug 5 - Tue, Aug 11
ORD
Chicago
MIA
Miami
$171 Roundtrip, just found
$171
Roundtrip
just found
Select United flight, departing Wed, Aug 5 from Chicago to Miami, returning Tue, Aug 11, priced at $171 just found

Sunny Isles Beach economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sea Club Resort
3.0-star property

Sea Club Resort

5.4/10 (1,012 reviews)

Aug 15 - Aug 22

7 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $538, price is now $306 per person
$306
per person
found 1 day ago
In my own experience, my room was clean and neat , the staff is mixed, so you may have a nice genuine salute or just a cold formal interaction, the personal at the hotel didn't mention proactively about any amenities that the hotel offers, the customer need to ask the questions one by one if you need information ( My check in was on Friday May 18) .The hotel has parking lot which is one spot per room included (reasonable) The beach is just in front, a very nice experience in general . There is a balcony in the property facing the beach but unfortunately that area was closed . Recommendations : they should paint the bathtubs in the bathroom, even they are in good working conditions ; still a proper ventilation in the bathroom is needed.

Reviewed on May 24, 2026

Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,002 reviews)

Aug 6 - Aug 9

3 night stay

Chicago (CHI) to Miami (MIA)

United • Roundtrip • Coach
Save 100% on your flight
Price was $670, price is now $395 per person
$395
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

May-Dee Suites
2.5-star property

May-Dee Suites

9.4/10 Exceptional! (1,497 reviews)

Aug 15 - Aug 22

7 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $577, price is now $344 per person
$344
per person
found 1 day ago
Let me start by saying that it really disappoints me when I see reviews and they say somewhere is exceptional-this property is a good place to lay your head for a night if you’re going through town. The room was clean enough, but it isn’t somewhere that I would want to stay for more than a few hours. I really wish these hotel rooms in Florida would put in some sort of air purifying systems because they all smell like mold unless you’re going to stay in a very high-end situation. They do keep it up, but I don’t really like to lay with bedding that you can tell everybody else has been using meaning the comforter, etc. I would like to see that changed out and they should just stick to solid white because that cleans well. parking is very limited. I was lucky to get a space out in the front. I think it was because it was a Monday. If I wasn’t you will have to park around the back that seemed incredibly uncomfortable to me coming by myself as a female overall it’s clean and like I said a decent place to lay your head, but if you’re planning on a vacation and you want a nice place to come back and stay this isn’t the situation

Reviewed on Apr 13, 2026

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Sunny Isles Beach packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Miami-Airport South-Blue Lagoon
2.5-star property

Hampton Inn & Suites Miami-Airport South-Blue Lagoon

9/10 Wonderful! (2,129 reviews)

Aug 7 - Aug 10

3 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $689, price is now $630 per person
$630
per person
found 1 day ago
The service desk employee was extremely helpful.

Reviewed on Jun 22, 2026

Leslie Hotel Ocean Drive
4.0-star property

Leslie Hotel Ocean Drive

9/10 Wonderful! (1,006 reviews)

Aug 7 - Aug 10

3 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $885, price is now $722 per person
$722
per person
found 1 day ago
Everything was great

Reviewed on Jun 10, 2024

Hotel St. Michel
3.5-star property

Hotel St. Michel

9.4/10 Exceptional! (1,008 reviews)

Aug 7 - Aug 10

3 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $784, price is now $698 per person
$698
per person
found 1 day ago
This property offers a charming throwback in time with a distinct vintage feel. It features beautiful wooden floors and an old school elevator complete with an operator, adding to its nostalgic character. Room access is via traditional physical keys, which further enhances the classic experience. The hotel is very intimate, with only 28 rooms, and is ideally located in the heart of Coral Gables within walking distance of several restaurants, banks, and a Target. While the property does not offer an extensive range of amenities, it does include an Italian restaurant on the first floor. Overall, it was a very pleasant and unique stay.

Reviewed on Apr 29, 2026

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Sunny Isles Beach business class flight packages

Price found within the past 48 hours. Click for updated prices.
The Sunny
4.0-star property

The Sunny

8.8/10 Excellent! (387 reviews)

Jul 30 - Aug 3

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,108, price is now $860 per person
$860
per person
found 1 day ago
This was our first time staying at The Sunny, but are very familiar with the area. My father lives a few blocks away and over the years we have sampled several of the loca properties. The transformation from the Newport to the Sunny is remarkable. The rooms are beautiful. The lobby is incredible. The real key is the pool deck. Most of the competition close by have very small pools, which are largely in the shade of the building. Not here. This is wonderful. The staff is top notch. Very well trained and they really go out of their way to make everything just right. I would say the hotel is 90% done. Still waiting for the restaurant to open. That will also enhance the poolside dining options as well. Go, you won’t regret it.

Reviewed on Apr 8, 2026

Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.4/10 Very Good! (8,366 reviews)

Jul 30 - Aug 3

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,428, price is now $1,047 per person
$1,047
per person
found 1 day ago
Overall experience was great! However, they need to fire the current house keeping. They’re lazy and you walk into a dirty room with stains and hair everywhere . Thank God they upgraded me to a one bedroom suite which made me give them a 5 star. There were dozens of people complaining of dirty rooms. Fire management if they cannot hire quality housekeepers.

Reviewed on Jun 2, 2026

Eden Roc Miami Beach
4.5-star property

Eden Roc Miami Beach

8.6/10 Excellent! (3,291 reviews)

Jul 30 - Aug 3

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,357, price is now $1,049 per person
$1,049
per person
found 1 day ago
Very communicative hotel. Super friendly and professional

Reviewed on Mar 8, 2026

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Sunny Isles Beach first class flight packages

Price found within the past 48 hours. Click for updated prices.
Old Wooden Bridge Resort and Marina
2.5-star property

Old Wooden Bridge Resort and Marina

8.6/10 Excellent! (347 reviews)

Aug 5 - Aug 9

4 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,580, price is now $1,429 per person
$1,429
per person
found 1 day ago
Love this place and the staff. Friendly and helpful and the area is relaxing and beautiful

Reviewed on Jan 1, 2024

Sugarloaf Key Hotel at KOA Resort
3.0-star property

Sugarloaf Key Hotel at KOA Resort

9.8/10 Exceptional! (584 reviews)

Aug 5 - Aug 9

4 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $2,030, price is now $1,757 per person
$1,757
per person
found 1 day ago
The hotel was VERY clean and well-appointed as hotel kitchenettes go. Everything was new and well maintained. Some curiosities. ZERO closet space. So, for an extended stay facility you mostly had to live out of your suitcase. No ceiling fans. They did provide a floor fan. Biggest issue for us as we only stayed 2 nights, was the shower. It was very roomy with a rainfall head and a wall shower head, but the floor was literally as slippery as wet ice! They did provide a small shower mat that we felt was insufficient in size. If you stepped off the mat, you risked a fall. The bed mattresses were poor at best. Lots of outdoor "toys" and water activities. The grounds were immaculate. We would go back.

Reviewed on Jun 8, 2026

Parmer's Resort
2.5-star property

Parmer's Resort

9/10 Wonderful! (1,012 reviews)

Aug 5 - Aug 9

4 night stay

Chicago (CHI) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,735, price is now $1,606 per person
$1,606
per person
found 1 day ago
Can’t say enough good things about the staff location and amenities. All around best place to stay one night or a whole week. From kayaking to relaxing in the hammocks , to cozying up in your cottage, to the nice little breakfast, all things considered best place. Convenient to good places to eat within walking distance. Loved out stay here. Will definitely be back

Reviewed on Apr 18, 2026

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More About Flying To Sunny Isles Beach from Chicago

Route Information for Flights from Chicago to Sunny Isles Beach

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

Chicago to Sunny Isles Beach

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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.