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Festival travel: Chicago's Lollapalooza is coming soon, a flight away from Jacksonville

Photo: iStock
By Hoodline - 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 more than 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.

It’s more doable than you think. According to travel site Skyscanner, there are plenty of flights from Jacksonville to Chicago in that time frame, and the prices aren't too shabby.

So if you're looking for a change of scenery, here are some deals to put on your to-do list. (Prices and availability are current as of publication and subject to change.)

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.

Flight deals to Chicago

Currently, the cheapest flights between Jacksonville and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 6. Frontier Airlines currently has round-trip tickets for $171.

If you fly out of Jacksonville on Aug. 1 and return from Chicago on Aug. 8, Frontier Airlines currently has round-trip tickets for $176.

Top Chicago accommodations

To plan your accommodations, here are two of Chicago’s top-rated hotels, that we selected from Skyscanner's listings based on price 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 Hotel. 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. Set in the heart of Chicago, this hotel is close to the Hancock Building, Water Tower Place, the Tribune Tower and the Wrigley Building.

Local restaurant picks

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

Giordano's (730 N. Rush St.)

Photo: Trip by Skyscanner

One of Chicago's most popular restaurants is Giordano's, which has an average of 4.3 stars out of 113 reviews on Skyscanner.

Visitor Ulani wrote, "Got cheese curds this time which were yummy! Minestrone soup was chock-full of veggies and tasty. Pizza, as always, was crisp on the crust and ooeey-gooey inside."

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

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 classy and cozy ambience is perfect for a romantic date."

The Purple Pig (500 N. Michigan Ave.)

Photo: Trip by Skyscanner

Also worth considering is The Purple Pig.

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

"This place is perfect for brunch," wrote Maggie. "Every dish was delicious!"

Ema (74 W. Illinois St.)

Finally, there's Ema.

If you're into dipping and snacking, Ema is the place for you, because the menu is concentrated on spreads, dips and snacks with a Mediterranean/Californian flavor. Spicy hummus or an avocado and green pea spread are highlights, or try pan-roasted romanesco cauliflower with yogurt and honey.

Reviewer Julie wrote, "I suggest their roasted potatoes and rosemary, beef kebab and the shredded romaine lettuce salad. We finished the meal with fresh hot tea."

Featured local attractions

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

Millennium Park (201 E. Randolph St.)

Photo: Trip by Skyscanner

First up is Millennium Park.

It is the most famous section of Grant Park, and is home to most of the park’s highlight attractions, namely the Cloud Gate sculpture, nicknamed The Bean. The park is one of the largest green roofs in the world, as it was built on top of parking garages and a railroad yard.

"Love, love, love Millennium Park in all seasons," wrote visitor Marcia. "My child enjoys going there for movies, dancing events, really every reason a child could have a blast."

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

Photo: Trip by Skyscanner

Next, there's The Art Institute of Chicago, 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."

"Free family play area and thinking lounge off the Modern wing," wrote visitor Ulani. "Simple, quiet indoor space for all ages to relax after shopping or visiting the park."

Willis Tower (233 S. Wacker Drive)

Finally, spend some time at 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 its construction was finished in 1974, it was the world’s tallest building at 1,451 feet.

Visitor Yvonne wrote, "We waited in line to step out onto the glass floor, which was pretty cool. Great views of the city and on a clear day you can see out across Lake Michigan."


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.

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