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Festival travel: Escape from Portland to Chicago for Lollapalooza

Festival travel: Escape from Portland to Chicago for Lollapalooza
Photo: iStock
By Hoodline - Published on July 15, 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 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.

Thankfully, there are plenty of regular, relatively inexpensive flights between Portland and Chicago. We pulled from travel site Skyscanner to provide you with a short list of flights and hotels handpicked for the occasion. (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

The cheapest flights between Portland and Chicago are if you leave on Aug. 1 and return from Illinois on Aug. 7. Spirit Airlines currently has tickets for $309, roundtrip.

If you fly out of Portland on Aug. 1 and return from Chicago on Aug. 6, United can get you there and back for $352 roundtrip.

Top Chicago hotels

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

For an all-around top recommendation, consider The Palmer House a Hilton House. The hotel has a 4.5-star rating on Skyscanner.

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.

TheWit — A DoubleTree by Hilton (201 N. State St.)

Photo: Trip by Skyscanner

Another option is TheWit — A DoubleTree by Hilton. The 4.8-star hotel has rooms for $249/night. Recreational amenities include a health club and a fitness facility.

"With its modern rooms, great views and rooftop bar, theWit is a great place for a Chicago weekend stay or even for a night out. The rates are very reasonable for its location and totally worth it," wrote visitor Sara.

Featured Chicago food and drink

Chicago has plenty of top-notch dining options. Here are a few of the most popular, according to Skyscanner.

Portillo's (100 W. Ontario St.)

Photo: Trip by Skyscanner

One of Chicago's most popular restaurants is Portillo's, which has an average of 4.4 stars out of 106 reviews on Skyscanner. Portillo's first "Dog House" opened in 1963 and this Chicago classic has never looked back.

"A must-have if you are coming to visit Chicago," wrote Joseph. "Portillo's is a cornerstone in tourist eateries for good Italian beef and Chicago-style dogs."

Giordano's (730 N. Rush St.)

Photo: Trip by Skyscanner

Another popular dining destination is Giordano's, with 4.3 stars from 114 reviews.

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."

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

Photo: Trip by Skyscanner

Also worth considering is The Signature Room at the 95th atop the John Hancock Center.

The high-end restaurant 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."

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

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

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

Top Chicago attractions

To round out your trip, Chicago offers plenty of popular attractions worth visiting. Here are some top recommendations, based on Skyscanner's descriptions and reviews.

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, 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.)

Photo: Trip by Skyscanner

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)

Photo: Trip by Skyscanner

Finally, consider checking out 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.