Chicago/ Fun & Entertainment
Published on March 14, 2019
Travel watch: Chicago to Miami, and back againPhoto: iStock

If you're looking for an international escape but want to keep your passport at home, consider planning a vacation to Miami, Florida. The worldly city is located on Florida's southeastern tip. Its Cuban influence is reflected in the cafes and cigar shops that line Calle Ocho in Little Havana.

On barrier islands across the turquoise waters of Biscayne Bay is Miami Beach, home to South Beach. This glitzy neighborhood is famed for its colorful art deco buildings, white sand, surfside hotels and trendsetting nightclubs. Glamour aside, the city has plenty of quality restaurants, bars and attractions to appease any budget traveler.

Fortunately, there are plenty of relatively inexpensive flights between Chicago and Miami, at least according to travel site Skyscanner.

Here’s a list of flights, hotels, restaurants and local attractions in Miami to get you started.

(Hoodline offers data-driven analysis of local happenings and trends across cities. Links included in the articles may earn Hoodline a commission on clicks and transactions. Prices and availability are subject to change.)

Flight deals to Miami

The cheapest flights between Chicago and Miami are if you leave on May 6 and return from Florida on May 9. American Airlines currently has tickets for $157, roundtrip.

American Airlines also has tickets at that price point in June. If you fly out of Chicago on June 1 and return from Miami on June 5, American Airlines can get you there and back for $157 roundtrip.

Top Miami hotels

To plan your accommodations, here are some of Miami’s top-rated hotels, that we selected from Skyscanner's listings based on price and customer satisfaction.

The Fontainebleau Miami Beach (4441 Collins Ave.)

Photo: Trip by Skyscanner

If you're looking to splurge on top quality, consider The Fontainebleau Miami Beach. The hotel has a 4.5-star rating on Skyscanner, and rooms are currently available for $399.

The Fontainebleau Miami Beach overlooks the beach and stands three miles from South Beach and the Lincoln Road shops.

The W South Beach (2201 Collins Ave.)

Photo: Trip by Skyscanner

There's also the 4.6-star rated The W South Beach. Rooms are currently set at $359/night.

Some of the city's most popular beaches and hottest nightlife, along with John Collins Park, are just steps away from this oceanfront hotel. 

The Mandarin Oriental, Miami (500 Brickell Key Drive)

Photo: Trip by Skyscanner

A third option is The Mandarin Oriental, Miami. It has a 4.9-star rating on Skyscanner, and rooms are currently listed for $299/night.

Featured Miami food and drink

If you're looking for a popular spot to grab a bite, Miami has plenty of excellent eateries to choose from. Here are a few from Skyscanner's listings to help you get started.

Joe's Stone Crab (11 Washington Ave.)

Photo: Trip by Skyscanner

If you're looking for a local favorite, head to Joe's Stone Crab, which has an average of 4.6 stars out of 87 reviews on Skyscanner.

"Food and service were first class," visitor Shane wrote. "We’ve lived in Miami for two years and always felt Joe’s was a place for tourists but it’s so much more than that."

Versailles Cuban Restaurant (3501 S.W. Eighth St.)

Photo: Trip by Skyscanner

Another popular dining destination is Versailles Cuban Restaurant, with 4.4 stars from 93 reviews.

"This is the most famous Cuban restaurant in Miami," reviewer James wrote. "Many U.S. Presidents have stopped by to experience the restaurant when visiting Miami."

Zuma (270 Biscayne Blvd. Way)

Photo: Trip by Skyscanner

Also worth considering is Zuma.

"The service and food are consistently outstanding," wrote Kayla.  

Mandolin Aegean Bistro (4312 N.E. Second Ave.)

Photo: Trip by Skyscanner

Finally, there's Mandolin Aegean Bistro.

"This is a fantastic restaurant," wrote Shane. "I’d highly recommend the grilled octopus, the meze, the kefte meat balls and the Greek salad. The wine list is also very reasonable."

What to see and do in Miami

Not sure what to do in Miami, besides eat and drink? Here are a few recommendations, provided by Skyscanner.

Vizcaya Museum and Gardens (3251 S. Miami Ave.)

Photo: Trip by Skyscanner

First up is the Vizcaya Museum and Gardens, the villa that Pope John Paul II has visited in the past. Take walks through the gardens, spend some time at the waterfalls and fountains and take pictures at the reflecting pools.

"It's well worth a half-day visit," wrote visitor Shane. "The gardens are lovely and good fun for kids to run around and get lost. There are great views across to Key Biscayne, too."

Miami Design District (3841 N.E. Second Ave.)

Photo: Trip by Skyscanner

The Miami Design District is another popular destination.

"See everything from photography and sculpture to graffiti and street art and more," wrote visitor Arcelia. 

Wynwood Walls (2520 N.W. Second Ave.)

Photo: Trip by Skyscanner

Lastly, consider checking out the Wynwood Walls.

Wynwood Walls is a permanent outdoor mural exhibit featuring some of the world's most renowned street artists. Additionally, there are hundreds of other street art and graffiti murals around the district curated by Primary Flight, making it one of the biggest street art districts in in the world.

This story was created automatically using flight, hotel, and local attractions data, then reviewed by an editor. Click here for more about what we're doing. Got thoughts? Go here to share your feedback.