Festival travel: Chicago hosts Lollapalooza, with cheap flights from Miami

Festival travel: Chicago hosts Lollapalooza, with cheap flights from MiamiPhoto: iStock
Published on July 10, 2019

It's the grandaddy of modern music festivals and it's still going strong. Book your trip to Chicago from Aug. 1-4 for this year's Lollapalooza.

Headline acts include The Strokes, Childish Gambino and Ariana Grande, but over 170 acts from all over the world will play the festival's eight stages. Offstage look for plenty of food and drinks, merch and kid-friendly offerings, along with space for visual arts.

The festival plays out in Grant Park, nestled in the Windy City's Loop overlooking Lake Michigan and convenient to the city's vast cultural and culinary offerings.

Fortunately, there are plenty of relatively inexpensive flights between Miami and Chicago on travel site Skyscanner.

Here’s a list of flights, hotels, restaurants and local attractions in Chicago to round out your trip. (Prices and availability are current as of publication and subject to change.)

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Flight deals to Chicago

The cheapest flights between Miami and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 6. American Airlines currently has tickets for $215, roundtrip.

If you fly out of Miami on Aug. 1 and return from Chicago on Aug. 8, American Airlines can get you there and back for $240 roundtrip.

Top Chicago accommodations

To plan your accommodations, here are two of Chicago’s top-rated hotels, according to Skyscanner, that we selected based on price, proximity to things to do and customer satisfaction.

The Palmer House a Hilton House (17 E. Monroe St.)

Photo: Trip by Skyscanner

If you're looking for an inexpensive place to stay, consider The Palmer House a Hilton House. The hotel has a 4.5-star rating on Skyscanner, and rooms are currently available for $92.

The hotel is a lively destination within walking distance of the best attractions the city of Chicago has to offer, like Millennium Park, Grant Park, Lake Michigan, the Art Institute of Chicago, the theater district and the Magnificent Mile.

The Raffaello Hotel (201 E. Delaware Place)

Photo: Trip by Skyscanner

Another option is The Raffaello Hotel. With a five-star rating on Skyscanner, the hotel is one of the most luxurious in the city. Rooms are currently listed for $99/night.

It's close to the John Hancock Center, Water Tower Place and the Tribune Tower. 

Top picks for dining and drinking

Chicago has plenty of top-notch dining options. Here are a few of the most popular, according to Skyscanner.

Giordano's (730 N. Rush St.)

Photo: Trip by Skyscanner

If you're looking for a local favorite, head to Giordano's, which has an average of 4.3 stars out of 114 reviews on Skyscanner.

Visitor Ulani wrote, "I got cheese curds and they were yummy! The minestrone soup was chock-full of veggies and very tasty."

The Signature Room at the 95th (875 N. Michigan Ave.)

Photo: Trip by Skyscanner

Another popular dining destination is The Signature Room at the 95th, with 4.5 stars from 65 reviews.

The Signature Room at the 95th, atop the John Hancock Center, offers diners a 360-degree skyline view, with floor-to-ceiling windows. There's a lunch buffet Monday through Saturday and dinner nightly with seafood, steaks and chops.

"I love this place for the food and the awesome views of Chicago," wrote reviewer geminitraveller. 

The Purple Pig (500 N. Michigan Ave.)

Photo: Trip by Skyscanner

Also worth considering is The Purple Pig, with 4.6 stars from 46 reviews.

A collaboration among four top chefs, the Purple Pig specializes in "cheese, swine and wine."

Ghirardelli Ice Cream & Chocolate Shop (830 N. Michigan Ave.)

Photo: Trip by Skyscanner

Finally, there's the Ghirardelli Ice Cream & Chocolate Shop. It has five stars from five reviews on Skyscanner.

"I love the Ghirardelli chocolate ice cream. The ice cream is the perfect treat for warm summer days," wrote Celeny.

Top Chicago attractions

To round out your trip, Chicago offers plenty of popular attractions worth visiting. Here are some top recommendations, based on Skyscanner's descriptions and reviews.

Millennium Park (201 E. Randolph St.)

Photo: Trip by Skyscanner

First up is Millennium Park, which is a large public park and is the most famous section of Grant Park. It is home to most of the park’s highlights, including the Cloud Gate sculpture, nicknamed The Bean. The park is considered one of the largest green roofs in the world, as it was built on top of parking garages and a railroad yard. 

"I love Millennium Park in all seasons," wrote visitor Marcia. "My child enjoys going there for movies and dancing events. It’s worth going to check out."

The Art Institute of Chicago (111 S. Michigan Ave.)

Photo: Trip by Skyscanner

Another popular destination, The Art Institute of Chicago is an art museum in Chicago’s Grant Park.

It is most famous for its Impressionist and Post-Impressionist collections. Some of the more notable works include Monet’s "Haystacks," Toulouse-Lautrec’s "Moulin Rouge" and Edward Hopper’s "Nighthawks."

Willis Tower (233 S. Wacker Drive)

Photo: Trip by Skyscanner

Finally, consider checking out Willis Tower.

The skyscraper, formerly known as the Sears Tower (a name which is still commonly used), is actually nine square buildings bundled together; an engineering strategy to help the 110-story structure resist Chicago’s infamously high winds. When it finished construction in 1974, it was the world’s tallest building at 1,451 feet.

"There are great views of the city and on a clear day you can see out across Lake Michigan," wrote visitor Yvonne.

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.