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 San Jose and Chicago, at least according to travel site Skyscanner.
Here’s a list of flights, hotels, restaurants and local attractions in Chicago to get you started. (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.
Cheapest Chicago flights
Currently, the cheapest flights between San Jose and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 6. Delta currently has roundtrip, nonstop tickets for $375.
If you fly out of San Jose on Aug. 1 and return from Chicago on Aug. 5, Alaska Airlines can get you there and back for $394 roundtrip.
Top Chicago hotels
To plan your stay, 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.)
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)
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.
Local restaurant picks
If you're looking to snag a bite at one of Chicago's many quality eateries, here are a few popular culinary destinations from Skyscanner's listings that will help keep you satiated.
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 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.)
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.)
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.)
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.
Featured local 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, 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.)
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)
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.
