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How to Spend a Perfect Chicago Summer Vacation

Published on July 10, 2025

The eATLAS app offers a variety of app-guided tours featuring the extraordinary art, architecture, food, history, and neighborhoods of Chicago, available on-demand at your convenience.  The blog post below details the more conventional options available to Chicago residents and visitors.

By Dave Lifton (@daveeatschicago)

To get an overall feel of Chicago, particularly on the first full day, take an architecture tour. The cruises (Chicago Architecture Center, Shoreline Sightseeing, Wendella, and Chicago Fireboat Tours) consist of treks along the Chicago River, where a guide goes into detail about the skyscrapers, including the Wrigley Building, Marina City, and Merchandise Mart. 

A walking tour adds a few benefits. You’ll be able to see the dazzling interiors of buildings you might otherwise walk past, and you’ll have greater interaction with the guide. Check out Intrepid Urban Adventures, Chicago Architecture Center, Tours With Mike, and Bobby’s Bike Hike for the experience that best suits your interests. 

(Disclosure: The author is an Intrepid tour guide)

Especially in the summer, Millennium Park is essential. Its centerpiece, Anish Kapoor’s Cloud Gate (“The Bean”), is a 110-ton sculpture that reflects the skyline and yourself in inventive ways. Be sure to go underneath for a singular experience that challenges your sense of perspective. The park also includes the Crown Fountain, an interactive reflecting pool with the faces of Chicagoans projected onto 50-foot pillars that “spit” water every five minutes. Nearly every summer night, Pritzker Pavilion features free live music, from national and internationally known acts of all genres on Monday and Thursday to classical on Wednesday, Friday, and Saturday. Grab some food and beverages to go and sit out on the lawn for an idyllic evening. 

millennium park

To see the city from its highest points, check out Skydeck at the Willis Tower or 360 Chicago at the former John Hancock Center. Both provide outstanding views, but offer something different. Skydeck (1,353 feet) has The Ledge, a glass-enclosed balcony that sticks out four feet above the street. At 1,030 feet, 360 Chicago is lower, but is closer to Lake Michigan and has a bar on-site. Plus, the Tilt thrill ride is available for an additional fee. Although advance tickets can be purchased, it’s best to check with the weather forecast to plan your visit around the clearest skies.

Navy Pier has long been one of Chicago’s most popular attractions for visitors, with a giant Ferris wheel, the new Flyover, a large food court, incredible views of the skyline, and the best souvenir shops in town. However, it’s geared towards families (see our guide to family-friendly Chicago here), and most of its charms can often be lost on those without children. But in recent years, the pier has added more adult options, including Offshore (the world’s largest rooftop bar) and more upscale dining, such as Chef Art Smith’s Reunion and Lirica.

Then there are the museums. The Art Institute of Chicago is one of the world’s finest, with more than 300,000 works on display. It’s celebrated for its collections of Americana and French impressionism. The Museum Campus has three of the city’s most popular institutions—the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium—within walking distance of each other. 

If you decide to visit the Griffin Museum of Science and Industry, seven miles south of downtown, consider exploring the rest of Hyde Park. Highlights include Frank Lloyd Wright’s Robie House, Gothic architecture on the campus of the University of Chicago, DuSable Black History Museum, and Jackson Park’s Japanese Garden. Head up to E. 53rd St., where you’ll find an assortment of restaurants.  

A great way to save money for all of these is to purchase the Chicago CityPASS, which combines admission to the Shedd Aquarium and Skydeck, with your choice of three of the following: Shoreline Sightseeing architecture cruise, Field Museum, 360 Chicago, Griffin Museum of Science and Industry, Art Institute of Chicago, and Adler Planetarium. The combined savings can be up to $138 per person. 

For meals, a food tour will introduce you to three dishes for which the city is known: Deep-dish pizza, Italian beef, and the Chicago-style hot dog. Beyond that, there are other foods that originated within the city limits. Go to the market at the Palmer House to sample the original brownie, which was invented there in 1893 at the request of Bertha Palmer (even better, hit the lobby bar for the brownie old fashioned). Nearby is the Italian Village, where chicken Vesuvio was invented.  When you want dessert, go to one of the many Garrett Popcorn Shops downtown or The Original Rainbow Cone off the Magnificent Mile. 

Caramel popcorn

Although downtown has no shortage of excellent dining options, from fast food to fine dining, Chicago’s neighborhoods have plenty to offer. The West Loop has emerged as the city’s trendiest area, and you can find more innovative restaurants a few miles northwest of downtown in Ukrainian Village, Wicker Park, Bucktown, and Logan Square. 

Our ethnic enclaves are also culinary hotbeds. Pilsen on the Near West Side is the heart of the Mexican community, and you can take the “L” or the Water Taxi to Chinatown. For more Asian options, head to the Far North Side, where you can find Vietnamese and Thai cuisine on Uptown’s Argyle St., while Devon Ave. in West Ridge is the place for Indian and Pakistani cuisine. To save on transportation and not rely on rideshares, much of Chicago is accessible by bus or the “L.” You can buy one-, three-, or seven-day passes for unlimited rides. Another option for downtown sight-seeing is the open-topped Big Bus, which stops at 11 landmarks approximately every half-hour, with an audio guide that provides commentary.  Tickets can be purchased in 24-, 48-, or 72-hour increments.

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