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

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.

Headliners The Strokes, Childish Gambino and Ariana Grande will be among the more than 170 acts from all over the world performing on 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 along Lake Michigan and convenient to the city's vast cultural and culinary offerings.

Fortunately, there are plenty of relatively inexpensive flights between Oklahoma City and Chicago on 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.)

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Cheapest Chicago flights

Currently, the cheapest flights between Oklahoma City and Chicago are for departure on Aug. 1 and return from Illinois on Aug. 6. American Airlines currently has tickets for $281, roundtrip.

United can get you there and back for $292 roundtrip on the same dates.

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.)

Photo: Trip by Skyscanner

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)

Photo: Trip by Skyscanner

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.)

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."

"[T]his place is perfect for brunch," wrote Maggie. "Every dish was delicious! The fried pig ear came with kale (fried of course), 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 needless to say, they have many exotic cocktails here."

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 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.)

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

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."

"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 [and] create a unique journey map for a self-guided museum tour. Tweens and older may enjoy the lounge, where you can leave questions for the museum or pick a conversation starter to engage with your group."

Willis Tower (233 S. Wacker Drive)

Photo: Trip by Skyscanner

Lastly, 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.