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

Photo: iStock
By Hoodline - Published on July 10, 2019.

It's the granddaddy 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.

It’s more doable than you think. According to travel site Skyscanner, there are plenty of flights from Raleigh 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 Raleigh and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 8. United Airlines currently has roundtrip tickets for $132.

If you fly out of Raleigh on Aug. 1 and return from Chicago on Aug. 7, United Airlines can get you there and back for $132 roundtrip.

Top Chicago accommodations

To plan your stay, 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 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 Drake, A Hilton Hotel (140 E. Walton Place)

Photo: Trip by Skyscanner

Another option is The Drake, A Hilton Hotel. With a 4.5-star rating on Skyscanner, the hotel is one of the most luxurious in the city. Rooms are currently listed for $109/night.

The Drake is at the apex of Magnificent Mile shopping, its iconic sign prominent to those traveling south on Lake Shore Drive. Nearby attractions include Navy Pier, Oakton Street Beach and Millennium Park. 

Featured Chicago restaurants

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

If you're looking for a local favorite, head to Giordano's, which has an average of 4.3 stars out of 113 reviews on Skyscanner.

Visitor Ulan 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 ooey-gooey inside. Lunch special was $10."

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 classy and cozy ambience is perfect for a romantic date. Expensive place but worth the spend for the unforgettable experience."

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."

"Every dish was delicious," wrote Maggie. "The fried pig ear came with fried kale, the cheesy broccoli was unique with the tangy cheese sauce, the bone marrow didn't have much bone marrow but came with lots of buttery brioche bread, and meatballs."

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

Photo: Trip by Skyscanner

Finally, there's Ghirardelli Ice Cream & Chocolate Shop.

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

Top Chicago 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, 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

Then, 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. Kids can take part in free workshops, draw, build, read, create a unique journey map for a self-guided museum tour."

Willis Tower (233 S. Wacker Drive)

Photo: Trip by Skyscanner

Finally, spend some time at Willis Tower.

The skyscraper, formerly known as the Sears Tower, is actually nine buildings bundled together — an engineering strategy to help the 110-story structure resist Chicago’s infamous winds. When it finished construction in 1974, it was the world’s tallest building at 1,451 feet. It remains among the tallest in the United States, with a public observation deck featuring glass floors for a straight-down view.

"I went here many years ago when it was the Sears Tower, but they have upgraded it since then," wrote visitor Yvonne. "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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