$25 Cheap flight deals from Chicago (CHI) to Surfside (MIA)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Surfside

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, Nov 15 - Sat, Nov 22
MDW
Midway Intl.
MIA
Miami Intl.
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Midway Intl. to Miami Intl., returning Sat, Nov 22, priced at $175 found 1 day ago
Sat, Nov 15 - Mon, Nov 17
MDW
Midway Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$280 Roundtrip, found 21 hours ago
$280
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Nov 17, priced at $280 found 21 hours ago
Sat, Nov 15 - Mon, Nov 24
ORD
O'Hare Intl.
MIA
Miami Intl.
$311 Roundtrip, found 1 hour ago
$311
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to Miami Intl., returning Mon, Nov 24, priced at $311 found 1 hour ago
Sun, Nov 16 - Mon, Nov 17
RFD
Greater Rockford
FLL
Fort Lauderdale - Hollywood Intl.
$372 Roundtrip, found 4 days ago
$372
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Nov 16 from Greater Rockford to Fort Lauderdale - Hollywood Intl., returning Mon, Nov 17, priced at $372 found 4 days ago

Airfares from $25 One Way, $59 Round Trip from Chicago to Surfside

Prices starting at $59 for return flights and $25 for one-way flights to Surfside 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, Jan 1 - Sat, Jan 31
ORD
Chicago
FLL
Fort Lauderdale
$59 Roundtrip, found 2 hours ago
$59
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jan 1 from Chicago to Fort Lauderdale, returning Sat, Jan 31, priced at $59 found 2 hours ago
Sat, Dec 13 - Wed, Dec 24
MDW
Chicago
MIA
Miami
$59 Roundtrip, found 4 days ago
$59
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Dec 13 from Chicago to Miami, returning Wed, Dec 24, priced at $59 found 4 days ago
Tue, Dec 9 - Wed, Dec 10
ORD
Chicago
MIA
Miami
$63 Roundtrip, found 8 hours ago
$63
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Dec 9 from Chicago to Miami, returning Wed, Dec 10, priced at $63 found 8 hours ago
Thu, Jan 15 - Tue, Jan 20
MDW
Chicago
FLL
Fort Lauderdale
$120 Roundtrip, found 2 hours ago
$120
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Chicago to Fort Lauderdale, returning Tue, Jan 20, priced at $120 found 2 hours ago
Wed, Feb 18 - Sat, Feb 21
ORD
Chicago
FLL
Fort Lauderdale
$151 Roundtrip, found 3 hours ago
$151
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Chicago to Fort Lauderdale, returning Sat, Feb 21, priced at $151 found 3 hours ago

Surfside economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.4/10 Very Good! (1,004 reviews)

Dec 30 - Jan 3

4 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,828, price is now $943 per person
$943
per person
found 1 day ago
The property was decent, and maintenance and cleanliness were fine, but it's not been updated much, and they were short staffed. The room night price seemed high relative to value. Would recommend, as the staff they have is enthusiastic, and the location is in the midst of everything South Beach.

Reviewed on Apr 28, 2025

Hawks Cay Resort
4.0-star property

Hawks Cay Resort

8/10 Very Good! (1,011 reviews)

Dec 31 - Jan 4

4 night stay

Chicago (CHI) to Miami (MIA)

Frontier Airlines • Coach

Miami (MIA) to Chicago (CHI)

Spirit Airlines • Coach
Price was $3,676, price is now $1,723 per person
$1,723
per person
found 1 day ago
Front desk service was exceptional!! Thank you Ashley & Kim for assisting us on this last minute reservation.

Reviewed on Mar 21, 2025

Villas At Hawks Cay Resort
4.0-star property

Villas At Hawks Cay Resort

8.6/10 Excellent! (138 reviews)

Dec 22 - Dec 29

7 night stay

Chicago (ORD) to Miami (MIA)

Spirit Airlines • Non-stop roundtrip • Coach
Price was $4,543, price is now $2,289 per person
$2,289
per person
found 1 day ago
Great time great place.

Reviewed on Sep 21, 2025

Don't see what you're looking for?
See all available trips from Chicago to Surfside
View all trips

Surfside packages with premium economy flights

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

President Hotel

8.4/10 Very Good! (1,905 reviews)

Jan 4 - Jan 10

6 night stay

Chicago (MDW) to Miami (MIA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,295, price is now $813 per person
$813
per person
found 19 hours ago
Friendly staff and great location.

Reviewed on Jul 19, 2025

Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8.2/10 Very Good! (1,118 reviews)

Jan 4 - Jan 10

6 night stay

Chicago (MDW) to Miami (MIA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,294, price is now $1,326 per person
$1,326
per person
found 19 hours ago
I would wholeheartedly recommend the Miami Beach Riu. Not only was the entire hotel clean and kept clean throughout the day, the staff also did a wonderful job of being helpful and friendly.

Reviewed on Jun 23, 2025

EAST Miami
5.0-star property

EAST Miami

9.2/10 Wonderful! (3,480 reviews)

Jan 4 - Jan 10

6 night stay

Chicago (MDW) to Miami (MIA)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,172, price is now $1,313 per person
$1,313
per person
found 19 hours ago
Always a great stay at East Miami.

Reviewed on Sep 1, 2025

Don't see what you're looking for?
See all available trips from Chicago to Surfside
View all trips

Surfside first class flight packages

Price found within the past 48 hours. Click for updated prices.
Costa Hollywood Beach Resort
4.0-star property

Costa Hollywood Beach Resort

9/10 Wonderful! (3,673 reviews)

Dec 25 - Jan 2

8 night stay

Chicago (ORD) to Miami (MIA)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,003, price is now $2,316 per person
$2,316
per person
found 4 hours ago
Friendly and professional staff. Room was very clean.. The suite I stayed in had beautiful Ugg decor, and it had everything you'll need for a comfortable stay; micro, cook top & oven, kerig & regular coffee maker, even washer and drier, etc. There's plenty of places to eat, drink & party at walking distance on the boardwalk.. Valet parking is a must, hard to find regular parking, valet service was elite.

Reviewed on Aug 6, 2025

Solé Miami, A Noble House Resort
4.0-star property

Solé Miami, A Noble House Resort

8.4/10 Very Good! (1,885 reviews)

Dec 25 - Jan 2

8 night stay

Chicago (ORD) to Miami (MIA)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $3,730, price is now $2,406 per person
$2,406
per person
found 4 hours ago
Very nice good service and clean

Reviewed on Aug 22, 2025

Amrit Ocean Resort and Residences - Singer Island
5.0-star property

Amrit Ocean Resort and Residences - Singer Island

8.8/10 Excellent! (177 reviews)

Dec 25 - Jan 2

8 night stay

Chicago (ORD) to Fort Lauderdale (FLL)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $5,914, price is now $4,061 per person
$4,061
per person
found 4 hours 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

Don't see what you're looking for?
See all available trips from Chicago to Surfside
View all trips

More About Flying To Surfside from Chicago

Route Information for Flights from Chicago to Surfside

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

Chicago to Surfside

Orbitz assures that you will receive cheap air fares on flights from Chicago to Surfside and special deals that give you guaranteed low prices on hotels, cruises, car rentals, and anything else you need on your trip.

Free Orbitz mobile app for your Android or iPad

Get the latest Orbitz app for your smartphone and tablet to book low cost cars, hotels, and Chicago to Surfside flights. Our cutting-edge mobile tools let you view your trip itinerary on your mobile device anytime you need it. You can research great deals on highly rated hotels near you with the app, which uses your smartphone’s GPS, and book the one you like with just a few taps.

Orbitz mobile site for even more convenience

Use your mobile Web browser to get savings on flights from Chicago to Surfside. Our mobile site, m.orbitz.com, offers the same powerful search and other capabilities you expect from our regular site. Retrieve and share your itinerary for your from Chicago to Surfside flights with friends, family members, and colleagues, and browse photo galleries and user reviews of hotels to find the one you like.

Free alerts on flight and travel plans

Receive free, real-time updates on your low fare flights from Chicago to Surfside via your mobile phone or email inbox. Stay on top of delays, gate charges, and other event notifications so you can make other travel arrangements if you need to.

Low fares on Chicago to Surfside flights

Forget about annoying booking fees and get cheap air ticket sales as you make your reservations online with Orbitz. Follow Orbitz on Twitter and Facebook and get alerted about travel coupons and promo codes for Chicago to Surfside flights.

More Destinations

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.