Austin/ Health & Lifestyle
Published on July 10, 2019
Festival travel: Escape from Austin to Chicago for LollapaloozaPhoto: iStock

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 wondering what it would cost, take a look at these forthcoming flights between Austin 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

Currently, the cheapest flights between Austin and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 6. Spirit Airlines currently has tickets for $156, roundtrip.

If you fly out of Austin on Aug. 1 and return from Chicago on Aug. 7, Spirit Airlines can get you there and back for $161 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. Set in the heart of Chicago, this hotel is close to the Hancock Building, Water Tower Place and the Tribune Tower. 

Featured Chicago food and drink

Don't miss Chicago's food scene, with plenty of popular spots to get your fill of local cuisine. Here are a few of the top-rated eateries from Skyscanner's listings.

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.

"Best deep pizza I've had so far! Once you taste it you will see what all the local rave is about," wrote Kierriah C. "This is one stop you must make while visiting Chicago."

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 high-end food and a dazzling skyline view from the floor-to-ceiling windows. 

"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."

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.

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

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.)

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 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 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 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."

"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," wrote visitor Ulani. 

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.