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.
Whether you’re ready to book your trip now or just curious about the options, take a look at these forthcoming flights between Orlando and Chicago, which we pulled from travel site Skyscanner.
We've also included popular hotels, restaurants and attractions in Chicago to highlight the city's best for visitors headed there soon. (Prices and availability are current as of publication and subject to change.)
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Cheapest Chicago flights
The cheapest flights between Orlando and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 8. Allegiant Air currently has roundtrip tickets for $161.
If you fly out of Orlando on Aug. 1 and return from Chicago on Aug. 7, Frontier Airlines can get you there and back for $187 roundtrip.
Top Chicago hotels
Regarding where to 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 Hotel (17 E. Monroe St.)
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)
Another option is The Raffaello Hotel. With a five-star rating on Skyscanner, rooms are currently listed for $99/night. It's close to the John Hancock Center, Water Tower Place and the Tribune Tower.
Featured Chicago food and drink
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.)
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.)
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.)
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.)
Finally, there's Ghirardelli Ice Cream & Chocolate Shop.
"I love the Ghirardelli ice cream and chocolate selection," wrote Celeny. "The ice cream is the perfect treat for warm summer days."
Featured Chicago attractions
Chicago is also full of sites to visit and explore. Here are some popular attractions to round out your trip, again from Skyscanner's listings.
Millennium Park (201 E. Randolph St.)
First up is Millennium Park.
It is the most famous section of Grant Park and 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.
"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. It’s worth going to check out."
The Art Institute of Chicago (111 S. Michigan Ave.)
Then, there's The Art Institute of Chicago, an art museum in 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)
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.
"We waited in line to step out onto the glass floor, which was pretty cool," wrote visitor Yvonne. "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.