Scenic/ Historic Walking Areas in Chicago

Top Scenic Walking Areas in Chicago, IL

Scenic Walking Areas in Chicago

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    Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.
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    Highest rated attractions on Tripadvisor, based on traveller reviews.
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What travellers are saying

  • MadMike96
    Madison, WI46 contributions
    Great urban trail to walk, run, or bike. No cross traffic. Was not too busy on a weekday. Well maintained and lots of access points. 2.7 miles long.
    Written 21 June 2021
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Eva J
    Moscow, Russia2,698 contributions
    This sign isn't big, so it's easy to miss. I was looking for it, but I still almost missed it. I noticed it because I saw people taking selfies with the sign in the background. Does anyone drive route 66 starting from here?
    Written 21 January 2020
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Taylor B
    Chicago, IL7,720 contributions
    Ask 10 people familiar with the Wrigleyville neighborhood on Chicago's North Side to point out its borders on a map and you'll probably get 10 different answers. Irving Park Road or Grace Street to the north. Newport or Cornelia to the south. Sheffield or Fremont or Halsted to the east. Southport or Racine or Ashland to the west. Go figure. But everybody agrees that Wrigleyville is a popular year-round destination for locals and tourists who enjoy what the area around Clark and Addison has to offer--restaurants, bars, entertainment venues, souvenir stalls and gift shops--whether the hometown favorite Chicago Cubs are playing or not. Established in 1914, Wrigley Field is the centerpiece and namesake of this former working-class neighborhood. Today, it is a tourist hub that swells with activity during Cubs home games. It is densely populated with lively sports bars and cool pubs. Baseball-themed gift shops line Sheffield, Addison and Clark Streets. Iconic Metro, a 1,000-seat music hall which opened in 1982, has hosted shows by Bob Dylan, Nirvana, R.E.M. and Kanye West. Outside Wrigley Field is open-air Gallagher Way, a popular gathering place for neighbors, locals and visitors all year long. It hosts farmer markets, outdoor concerts and film screenings. When the Cubs play at home, fans without tickets watch the game on a large screen in Gallagher Way. Suggestion: If you are going to a game, take the Addison Street or Clark Street bus. Don't try to drive and park. During the offseason, arrange to tour the stadium and learn by Wrigley Field's storied past. Or go to the Music Box Theatre, which opened in 1929 and is the city's premier cinema for independent movies, documentaries, foreign films and adult classics. And you can buy a bag of popcorn with real butter. The atmosphere during the games is always exciting, especially if you sit in the bleachers or the rooftops, but fans experience even more fun after the last pitch when they gather at one of Wrigleyville's restaurants or bars. Favorites include Murphy's Bleachers, the favorite watering hole of tried-and-true Cubs fans, the Cubby Bear, GMan Tavern and Nisei Lounge, which opened in 1951 and is the oldest bar in Wrigleyville. Other popular venues include Byron's Hot Dogs, Lucky's Sandwich Company, Lowcountry, Cozy Noodles & Rice, Uncommon Ground, Budweiser Brickhouse Tavern, Sluggers, Shake Shack, Mordecai, Smoke Daddy BBQ, Big Star Wrigleyville, Bernie's Tap & Grill, Goose Island, Rockit Burger Bar and Guthrie's Tavern. In Wrigleyville, the game is a bonus.
    Written 8 October 2020
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Taylor B
    Chicago, IL7,720 contributions
    Promontory Point on Chicago's South Side has been known in recent years as the site of Barack and Michelle Obama's first kiss. But it's much more than that. Its view of Lake Michigan and Chicago's skyline may not be as scenic as the view from North Avenue Beach but it is an attractive piece of landscape. Located at 55th Street in Chicago's Hyde Park neighborhood, Promontory Point or The Point is a man-made peninsula jutting into Lake Michigan that was opened to the public in 1937. It was constructed from landfill and by the late 1930s was protected by a seawall or revetment that consists of limestone blocks arranged in a series of four steps leading to a promenade. The 12-acre peninsula, which contains a fieldhouse and was a popular destination for swimmers, sunbathers and windsurfers in the pre-pandemic period, can be accessed by the Lakefront Trail and a tunnel which passes under South Lake Shore Drive at the east end of 55th street, in the shadow of the Museum of Science and Industry. With its view of Navy Pier and Chicago's skyline and Lake Michigan, and the presence of stone sitting rings or fire pits that date to 1938, Promontory Point is a popular wedding and corporate event location and an area for family picnics. And first kisses.
    Written 28 October 2020
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • KatiaenJohan
    Hemiksem, Belgium271 contributions
    Walk down the boardwalk along the Chicago river and find a nice spot across from the Mart building. We saw two shows (one of which was designed by Nick Cave) and I liked them both a lot.
    Written 8 August 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Irina
    United States10,117 contributions
    Polk Bros Park is a beautiful, modern park, and it is a welcoming gateway to Navy Pier.

    A 13-acre park has two main areas, one is highly recreational, featuring a huge 12500 sq. ft. (1161.3 sq. m) Fountain with about 200 programmable jets -- a real gem and entertainment for kids on a hot summer day! This part of the park is beautifully landscaped; a very memorable 12-ft. tall Meet Me at the "P" aluminum sculpture adds a bright orange color to the overall green scenery of the Plaza, that is very comfortably appointed with large benches, many of which are placed under the shade of the trees.

    Another part of Polk Bros Park -- two large performance lawns -- is very functional, hosting various cultural events, arts festivals, and fitness classes in the open air. The most exciting feature of this part of the park is its unusual, vanguard design: one of the lawns faces the turquoise Lake Michigan, the opposite one gives some spectacular views of the Chicago Skyline!

    Polk Bros Park was established in 2014. The $20 million legacy gift was given to Navy Pier by the famous Chicago benefactors -- Polk Bros. Foundation to build this beautiful park.

    The park is very attractive and pleasant to visit, especially now, in summer -- it combines the beauty of nature with a contemporary, innovative design, it is highly popular, both with Chicagoans and visitors, and it was very enjoyable to visit!
    Written 12 July 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Ken P
    Atlanta, GA16 contributions
    We enjoyed touring the graffiti art in Pilsen, both along 16th street, as well as the main commercial district on 18th Street. If you go, check out Don Pedro Carnitas for lunch, and La Michoacána Premium for ice cream for dessert. Both were excellent!
    Written 12 July 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Rob H
    Rotterdam, The Netherlands251 contributions
    I think best place to see the Chicago skyline. I was there in the morning and had a beautiful blue sky. After I came out of the Adler Planetarium the weather changed but even that got a good photo.
    Written 20 June 2017
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Allen21096
    Chicago, IL29,714 contributions
    They just do not design and build park field houses like they used to. In 1928, the West Park Commission constructed the "Gold Dome Building" in Garfield Park to provide a new administrative headquarters for the West Park Commission. In 1934, the West Park Commission and the 21 other independent park commissions were merged in to the Chicago Park District and the field house, became just that - a field house for Garfield Park. The building itself houses a gymnasium, auditorium, dance studio, fitness center, boxing center, grand ballroom and meeting rooms. Garfield Park, itself, totals 184.72 acres and features the historic Golden Dome field house. There are two lagoons and the park is just south of the Garfield Park Conservatory. As beautiful as the exterior is, take a walk inside of the building and check out the interior. This building is a great example of a golden age of architecture of public buildings in Chicago.
    Written 29 January 2018
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
  • Lori T
    Dawsonville, GA2,497 contributions
    Based on the previous review which so eloquently documents the history of this point, we stopped to take a look. We found the National Park Service historical marker at the northeast corner of the bridge, though it did not provide the historical context. From this vantage point, we saw great views of the riverfront skyline. Worth taking a moment to see if you are in the area.
    Written 16 May 2021
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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