Things to do in Chicago, Illinois (IL): The Best Scenic Walking Areas

December 22, 2021 Brandee Mangan

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Promontory Point

5491 S Shore Dr, Chicago, IL 60615-5983 http://www.chicagoparkdistrict.com/parks/Burnham-Park
Excellent
75%
Good
25%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 8 reviews

Promontory Point

Reviewed By 866TaylorB - Chicago, United States

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.

2. Garfield Park Fieldhouse

100 N Central Park Ave, Chicago, IL 60624-1912 +1 312-746-5092 http://www.chicagoparkdistrict.com/parks/GA
Excellent
75%
Good
25%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 4 reviews

Garfield Park Fieldhouse

3. Solidarity Drive

E. Solidarity Dr., Chicago, IL 60605
Excellent
75%
Good
25%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 4 reviews

Solidarity Drive

4. Wrigleyville

Bordered by Halsted St On The East, Ashland Ave On The West, Chicago, IL
Excellent
45%
Good
45%
Satisfactory
7%
Poor
3%
Terrible
0%
Overall Ratings

4.5 based on 29 reviews

Wrigleyville

Reviewed By 866TaylorB - Chicago, United States

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.

5. Art on theMART

278-294 W Wacker Dr Built into the Riverwalk., Chicago, IL 60606 http://www.artonthemart.com
Excellent
67%
Good
33%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 6 reviews

Art on theMART

6. The 606

1805 N Ridgeway Ave runs east-west to 3700 W. Bloomingdale, Chicago, IL 60647 http://www.the606.org/
Excellent
53%
Good
35%
Satisfactory
10%
Poor
2%
Terrible
0%
Overall Ratings

4.5 based on 102 reviews

The 606

Reviewed By 866TaylorB - Chicago, United States

The Bloomingdale Trail is a 2.7-mile elevated rail trail running east-west on the northwest side of Chicago. In 2015, it was converted into an elevated greenway, which forms the backbone of the linear park and trail network called The 606 that passes through the Chicago neighborhoods of Logan Square, Humboldt Park and West Town. At 2.7 miles, the Bloomingdale Trail is the longest greenway project of a former elevated rail line in the United States and the second longest in the world. So why is it called The 606? Because the system's numeric name is a homage to the city's Zip codes, the prefix for nearly all of which is 606. Used by walkers, joggers, runners and bikers, the trail runs from Ashland Avenue all the way west to North Ridgeway Avenue. It follows along West Bloomingdale Avenue, hence the name Bloomingdale Trail. On a clear day, pedestrians on the trail get a spectacular view of Chicago's skyline.

7. Polk Bros Park

600 E Grand Ave, Chicago, IL 60611-3419 +1 800-595-7437 http://navypier.com/polk-bros-park/
Excellent
33%
Good
67%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 6 reviews

Polk Bros Park

Reviewed By O6378WFannag - Park Ridge, United States

I live in Chicago for more than 20 years but I don't visit Navy Pier too often. I was impressed on my recent visit to learn about new park with a lovely outdoor venue/amphitheater. Nicely kept. I like landscaping with prairie and native plants. Nice picnic area and some hidden picnic tables. Now I need to figure out if there are any concerts performed at that amphitheater with a gorgeous background: Lake Michigan.

8. 16th Street Murals

922 W. 16th St., Chicago, IL 60608 http://www.choosechicago.com/listing/16th-street-murals/56298
Excellent
67%
Good
33%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 3 reviews

16th Street Murals

Reviewed By 866TaylorB - Chicago, United States

Pilsen is a Chicago neighborhood where art comes to life around every corner, where bold murals and mosaics have blossomed in the most unexpected places--on the front of homes, along railway overpasses, on viaducts and wrapped around train platforms. Dozens of murals give visitors a marvelous look at Mexican art, culture, creativity and self-expression. Since the late 1960s, stretching from the Chicago River to Western Avenue, along 16th Street, the walls of an old railroad embankment host a vibrant and evolving outdoor gallery of murals by prominent and emerging local artists such as Mario Castillo, Hector Duarte, Jeff Maldonado, Ray Patlan, Marcos Raya, JC Rivera and Hebru Brantley and Belgian street artist ROA. What started as a protest to the Vietnam War and an effort to unify, inspire and educate Mexican-American residents about their proud heritage has more recently become an avenue and a canvas for rising and accomplished artists. Be sure to see the mosaics detailing the people and cultures of Pilsen at 1900 South Ashland Avenue. And Francisco Mendoza's glass-tile mosaics at Orozco Community College at 1645 West 18th Street. If you have time, visit the National Museum of Mexican Art. And be sure to take a lunch break at one of Pilsen's wonderful restaurants, including Monnie Burke's, Dusek's Board & Beer and Los Conales. My wife and I highly recommend the tacos at Carnitas Uruapan.

9. Route 66

Chicago, IL
Excellent
47%
Good
31%
Satisfactory
14%
Poor
7%
Terrible
1%
Overall Ratings

4.0 based on 91 reviews

Route 66

Reviewed By 490irinag - Illinois, United States

It's just a historic sign, but it means a lot in the greatest history of industrial development of this part of country and its important connection to the West. This sign marks the Beginning of Route 66, that starts at the corner of S Michigan Ave (opposite the Arts Institute), and goes on through Adams Street, and then further west and southwest, and all the way to California. ... History is on every street , at every corner, in every building, park, monument or sign in this fascinating city! ...

10. Jean Baptiste Point Du Sable Homesite

401 N Michigan Ave, Chicago, IL 60611-4255
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 1 reviews

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