CHICAGO LOVE: Our Favorite Places To Spend The Last Days Of Summer

There is just enough summer left for a short getaway – and luckily, Illinois is the 15th best state for road trips and 6th best for number of attractions, according to WalletHub. Many of these sites are in Chicago: the lakefront, various museums and Millennium Park. StreetWise vendors and staff give you their picks for a last grab at summer fun.

LAKEFRONT & WRIGLEY LOVE

My favorite place in the Chicago area is the lakefront between Oak Street and North Avenue Beaches, near the north end by the ladders, where it’s deeper and people can go swimming. When there’s more choppy waves, it’s great fun. It teaches you how to swim and have fun with the youth.

Going to Wrigleyville near Clark and Addison is another great experience. Lots of street vendors sell everything from magazines to water. It’s a fun, carnival atmosphere and you meet great people.

-Recommended by Vendor John Hagan

John Hagan

Lakefront

choosechicago.com

Wrigley Field

choosechicago.com

NAVY PIER

My favorite place is Navy Pier, where my grandparents met, and they were married for 50 years. I like the food, the rides, the walking for exercise, the friendly people and especially, the cruises on the river and the lake.

-Recommended by Participant Lisa Getches

Lisa Getches

Navy Pier

Navy Pier photo

C2E2

Enjoy a weekend that is the only comic, cosplay, and pop culture convention in the heart of Chicago. It is a gathering of A- to D-list celebrities, unique exhibitors, incredible comic artists, and larger-than-life literary authors in McCormick Place, 2302 S. King Drive, to celebrate pop culture fandoms. There is something for everyone, from a show floor packed with top exhibitors, autograph sessions, panels, screening rooms, exclusive souvenirs, After Dark events and a massive Artist Alley. If you’ve always dreamed of attending the biggest geek party in the Midwest, then look no further. This is your weekend to get wild and be free with other nerdy Chicagoans. Epic memories and awesome friendships await at Chicago Comic & Entertainment Expo (C2E2)! THIS WEEKEND! 10 a.m. - 7 p.m. August 5 & 6, 10 a.m. - 5 p.m. August 7. 3-day passes start at $99, daily passes start at $40 (and you can save even more if you purchase your pass at a local comic book store! May I suggest visiting our friends at Graham Crackers Comics Andersonville, 5028 N. Clark St.)

-Recommended by Publisher / Creative Director Dave Hamilton

C2E2

Reed Pop photo

C2E2

Reed Pop photo

C2E2

Reed Pop photo

GO EXPLORING!

I love Chicago for its attractions. You can be celebrating a special event, birthday, or just taking in what this wonderful city has to offer with friends on a nice day. Just the day before yesterday, I met two of my friends and had a wonderful time. We got on the Green Line and got off on State & Lake, walked down to the River Walk and enjoyed ourselves for a couple of hours, just soaking up the sun.

We made conversation with other people—who were also out with friends kickin’ it and having fun—and when evening came down, we walked to Millennium Park just to be doing something because, as we all know, time flies when you’re having fun! Before we knew it, we were walking down the Mag Mile, just looking at all of the very talented performers.

Soon, we were back on the Red Line, headed home. These were just a couple of the things we did as Chicago has so many things to do; that’s why I love my town, because I could go on and on about it. There’s just not enough pen and paper to do so, because, like I said, there is so much to see and do. If you are a true Chicagoan, you know just what I’m talking about.

So, until the next time pen and paper meet again, enjoy yourself and have all the fun you can handle!

-Recommended by Vendor Julius Vance

Julius Vance

River Walk

Choose Chicago

Millennium Park

Choose Chicago

A CHANGE OF SCENERY FOR 'WORK FROM HOME'

As a remote worker new to Chicago, I was on a mission to find spaces for both me and my laptop to enjoy. This meant free WiFi, accessible power outlets and an overall enjoyable environment available during business hours. And it’s only been a couple of months, but I’ve settled into a satisfactory cycle of WFH locations throughout the city. So, whether you’ve been working remotely since the start of the pandemic or you want to WFH without being at home, here are my favorite places in Chicago:

The first spot is on the second floor of the Merchandise Mart, 222 W. Merchandise Mart Plaza, the world’s largest commercial building. On your left after a few strides through the front door, you’ll see a flight of red-cushioned granite steps leading to an open ledge with a restaurant, bar and coffee bar: the industrial-modern Marshall’s Landing. While you’re more than welcome to order a bite of angry chicken fries, a hibiscus mule or a vanilla latte, you are free to work in this place without making a purchase. While sitting in a low, leather swivel chair and clacking away on my laptop, I feel elevated from the intern status to a professional businessperson waiting for a very important conference call. But in reality, I’m answering emails while HGTV or ESPN is projected on the large wall across from me.

My favorite WFH gem is the Winter Garden on the 9th floor of the Harold Washington Library, 400 S. State St. Its 52-foot glass-paneled dome invites the sun to bounce off the terrazzo and marble floor onto the powder blue walls and surrounding greenery. I always need a minute to appreciate the beauty before starting my tasks. This is a place designed for quiet work – it’s a very echoey room. Although there aren’t any power outlets to use, you can find plenty of them on the floors below. Get there earlier in the day to make sure you get a table!

-Recommended by Journalism Intern Emma Slings

Emma Slings

Winter Garden

Chicago Public Library photo

Marshall's Landing

Charles de Vaivre photo

GRANT PARK

Grant Park is often referred to as “Chicago’s Front Yard.” The most popular and populous places in Grant Park are clearly Millennium Park, Maggie Daley Park, the Petrillo Music Shell, and Buckingham Fountain.

But my favorite part of Grant Park is the south end, between the Museum Campus and Buckingham Fountain. My son opened my eyes to the area after a day at the Adler Planetarium. I had no idea there was a beach (12th Street Beach), nestled in between the Planetarium and Burnham Harbor. There are beautiful views of the lake and Monroe Harbor as the Lakefront Trail winds around the Shedd Aquarium. After crossing underneath Lake Shore Drive and the Metra tracks, you are suddenly in this lush oasis with stunning views of Chicago’s iconic skyline. The walking paths are tree-lined with beautiful gardens and fountains. The paths lead to open areas with park benches and grassy patches to sit and enjoy some shade with the lake breeze.

It’s almost unbelievable that this is nestled between Lake Shore Drive and Michigan Avenue; it's so quiet. You can easily forget that you are in a bustling city until you catch a glimpse of some of the skyscrapers through a break in the trees. Eventually you emerge into the open air near Buckingham Fountain. Just like that, you are back in the urban jungle. I highly recommend you explore this gem hidden in plain sight.

-Recommended by Executive Director Julie Youngquist

Grant Park

Julie Youngquist photos

Grant Park

Julie Youngquist photos

DuSABLE MUSEUM OF AFRICAN AMERICAN HISTORY

In 1961, Dr. Margaret Taylor Burroughs and her husband Charles established the Ebony Museum of Negro History, which later became known as the Jean Baptiste Pointe DuSable Museum of African American History, 740 E. 56th Place.

What drew me to the DuSable Museum was that I needed a sense of knowing about my history and culture. The DuSable Museum is the oldest African American history museum in the United States, with a collection of 15,000 paintings, sculptures and historical memorabilia. Every time I visit, I get a sense of purpose, a sense of belonging that helps me keep my focus on the things I need to accomplish. It helps me stay grounded.

What I am most proud of is that DuSable is credited for founding the trading post that became Chicago in 1779. The art there is overwhelming to see: pictures of ancient African artifacts and the story of indigenous peoples who were settled here. I feel that I really belong here in Chicago.

-Recommended by Vendor Lee A. Holmes

Lee A. Holmes

DuSable Museum of African American History

DuSable Museum of African American History photo

DuSable Museum of African American History

DuSable Museum of African American History photo

NORTH MICHIGAN AVENUE

One of my favorite places to visit in Chicago is the John Hancock Center and vicinity. When you go up to 360 Chicago on the 94th floor, you can look out the window and see all of Chicago and the lake. They also have a concession stand for souvenirs, snacks, and pop or beer. There's a restaurant on the 95th floor and lounge on the 96th.

And of course you don't want to miss Water Tower Place. It has an elevator you can ride to the top floor and hear a recording of Harry Caray singing TAKE ME OUT TO THE BALLGAME on your way to the Chicago Sports Museum. That part of downtown also has Sprinkles in Water Tower Place and at 50 E. Walton St., for Chicago's best cupcakes.

There's also a Starbucks Roastery at 646 N. Michigan Ave., which is something you have to see to be able to truly describe. You can order coffee on every floor, and it has one of the world’s only spiral escalators. Give it a try.

-Recommended by Vendor William Plowman

William Plowman

North Michigan Avenue

Mag Mile photo

Chicago Sports Museum

Mag Mile photo

ST. CLEMENT'S CHURCH

One of my favorite places to visit is St. Clement’s Church, 642 W. Deming Place in the Lincoln Park neighborhood. The reason is the kindness that the parish has shown me. I sell StreetWise before and after all three masses on Sunday. The priests, Father Matt and Father Peter, encourage people to buy them from me.

St. Clement’s was founded in 1905 by German-speaking immigrants along Lincoln Avenue and built in 1917-18 in the Byzantine style, with a dome like that of Hagia Sophia in Istanbul. St. Clement was the third successor to St. Peter as Bishop of Rome, and as pope.

I enjoy talking to Father Matt and Father Peter. To me, the Catholic ritual is no different than the Baptist: we stand up and pray, we give money and there’s a sermon. I look forward to going there every Sunday. Thank you, Father Matt and Father Peter, for being an inspiration to me.

-Recommended by Vendor Paula D. Holmes

Paula D. Holmes

Paula D. Holmes, Father Matthew Litak and Lee A. Holmes

Paula D. Holmes

Paula and Father Peter Wojcik

Paula D. Holmes

Interior of St. Clement's

Paula D. Holmes

ART INSTITUTE

I took a class there for painting when I was 18. I learned a lot about different painting techniques and a lot about what it means to be a struggling artist, how important it is in general to me and what an impact it has made in life.

-Recommended by Participant Tracy Byer

Tracy Byer

Art Institute of Chicago photo

ALL AROUND THE CITY

I have a couple of favorite places in Chicago. I like to go to the Skate Rink on Cottage Grove. You rent skates for $7 and you get to skate for hours. I can take my daughter. She can skate on her side and I can skate on my side with adults.

Then, another place I like is on the bike trail at Roosevelt. Dogs will be out playing. Skate boarders and people will be standing around feeding birds. You can park your bike and sit down and have a sandwich. There are sprinklers. There is so much to see riding your bike downtown on Roosevelt, or you can just ride over the bridge to the lakefront bike trail. It’s important to keep paper and garbage off the bike trail and, when riding on the trail, you have to be careful because people are jogging along the lake.

One day, I am going to park my bike and do some jogging myself. There are a lot of nice and free places to go and visit in Chicago, like the flower house – the Garfield Park Conservatory. You get off the CTA Green Line right in front of it. Check it out.

-Recommended by Vendor Kianna Drummond

Kianna Drummond

THE MUSEUM OF SCIENCE AND INDUSTRY

The Museum of Science and Industry has a lot of interesting discoveries — as soon as you finish climbing the entry stairs. You’ll observe the big pillars at the entrance and then once you enter, be fascinated by the hugeness of the space, including the airplane suspended from the ceiling.

Then, as you continue to work your way to the center, you will notice a huge pendulum hanging from the ceiling to the basement; it’s a timekeeper, or watch, of some kind. There are countless things to see and experience.

I remember as kids we used to stand on the footprints in front of this half-bubble made of glass, speak in the bubble and it would echo to the person some 30 feet behind you. You could even hear their whisper. That was simply amazing to me, like a sneak preview of cell phones.

Last, but not least, the real captured World War II German submarine that you can actually go into. When you enter, you can feel the closeness the men encountered while under the sea. They even have a periscope that you can look through to see up top, outside. It would be what the sailor would look through to see what was on the surface when they were underwater. It was a great experience, something you can’t read about, something that you must encounter. It’s just one museum that offers an educational experience.

-Recommended by Vendor A. Allen

A. Allen

Museum of Science & Industry

Museum of Science & Industry photo

Museum of Science & Industry

Museum of Science & Industry photo

A BIG CHICAGO FAN

We got festivals, the Taste of Chicago, the Air and Water Show; we can go to the Willis Tower; we can go on a boat ride. Chicago is very, very interesting. There’s always something to do. Okay. You’ve got the sports teams. People are friendly. The Friendly City. I’ve been here all my life. And I really enjoy it. That’s the most important thing to me: That I stay here. I can get around. I have a nice location selling magazines (Clark & Lake Streets during the day, Washington & Wells in the evening). Customers treat me right. Basically, do the right thing, and you’ll be okay.

I really enjoy going to the baseball games, the basketball games. StreetWise takes care of most of that for me, so I don’t have to pay a ton out of my pocket. That’s a good thing. I’m going to a WNBA game next month, and it’s because our staff heard us and worked with the Chicago Sky community-building team to help make this happen. I know I appreciate this.

Chicago is the peacefulest city, and it’s continuous entertainment. We got Navy Pier, baseball games, Millennium Park, Block 37—Chicago is a great city and I love it. Wouldn’t trade it for the world.

-Recommended by Vendor Russell Adams

Russell Adams

Chicago Air and Water Show

DCASE photo

Chicago Festival

DCASE photo

THE ART INSTITUTE OF CHICAGO

The Art Institute of Chicago has the largest collection of French Impressionist and post-Impressionist paintings outside Europe, so I bless my high school French teacher for sending us there for extra credit. As a teen, I was suddenly visiting on my own and on Saturday for a docent-led tour.

TripAdvisor named the Art Institute the top museum in the world in 2014 and I always recommend it to tourists. I’ve been to the Rijksmuseum in Amsterdam, the Uffizi in Florence, the Acropolis in Athens, the Museum of Anthropology in Mexico City, but I still rank the Art Institute right up there.

The reason is that its collection has fantastic cultural breadth, whereas marquee pieces in many other museums come primarily from their own nations.

The Art Institute guide to “What to See in an Hour” encompasses not only “The Bedroom” by Vincent Van Gogh and “A Sunday on LaGrande Jatte,” by Georges Seurat, for example, but also an African Face Mask and the “Buddha Shakyamuni Seated in Meditation.”

This guide is available online in a free app and in printed brochures/maps stacked right inside the entrance. I took the challenge on a Thursday, when the museum is open until 8 p.m. and crowds are smaller.

Normally, I would spend most of my time in 1870s-80s France with the Impressionists: Claude Monet haystacks and lilies, Edgar Degas dancers, Henri de Toulouse Lautrec at the Moulin Rouge. A copy of Monet’s “The Artist’s House at Argenteuil” (1873) hung in my college dorm room because his 5-year-old son in the picture resembled me in a painting my aunt did on the wall of her kitchen. She had taken classes at the Art Institute, so she depicted my family on the way to church on Sunday. I was wearing my red coat and hat, reaching up to hold my parents’ hands, my feet solidly placed, just like Monet’s son.

But the one-hour challenge means experiencing new art: African, Asian, Native American, modern American. Running up and down stairs, between the different wings of the Art Institute, you have enough time to see the pieces and read their labels, but not to overanalyze them, so there’s no pressure.

There’s a certain serendipity to it. “Nighthawks,” of a couple sitting together-but-alone in a New York City diner, was impossible to miss on the back wall of the “Arts of the Americas 1860-1950” gallery. On the way, I breezed by “The Wedding” by Jacob Lawrence.

Georgia O’Keeffe’s “Sky Above Clouds IV,” her memory of airplane travel, also dominates the wall over the stairway at the far east end of the museum. She undertook the 8-foot by 24-foot work in 1965, when she was 77, because she had always wanted to do a large mural. On the way to Pablo Picasso’s “The Old Guitarist” in the modern wing, I happened on a black reductionfired bowl with feather design by the Native American New Mexico artist Maria Martinez. I circled around it. Martinez’s nephew was the husband of an Hispanic artist who owned a bed and breakfast in Taos who became like a second mother to me after my own mother’s death.

Finally reaching the Picasso, I was inspired. Picasso became one of the most famous artists of all time, but when he painted the old, blind man in 1903-04, he was in the middle of his “Blue Period,” from poverty he had experienced the previous year.

-Recommended by Editor in Chief Suzanne Hanney

"Nighthawks" by Edward Hopper

Art Institute of Chicago photo

"The Artist's House at Argenteuil" by Claude Monet

Art Institute of Chicago photo

THE PEOPLE OF CHICAGO

My favorite things in Chicago all revolve around memories and people with whom they are shared. On more than one occasion, I have lucked into a conversation with a random person who knows the lakefront and the beauty of the “Rocks”—the outer and the inner.

I’ve discussed the differing quality of Harold’s Chicken restaurants (53rd Street location back in the day, anyone?). I’ve chatted about the childhood games we, in low-income housing, partook in, e.g., Red Rover (Red Rover, Red Rover, send Jazmine right over), Red Light/Green Light (I was the king of freeze!), Beat the Belt (ouch), Crate Ball (no basketball court? I’m still going to find a means to hoop), marbles (You’re not getting my boulder!). Basically, the people within the shared memories is where it’s at.

Which brings me to the television show “Good Times,” set in Cabrini-Green. I accepted every “Good Times” character as a person in my life, (not even subconsciously, I can sincerely say). To run into many, many random folks who could match me show-for-show regarding its episodes—especially the good ones—that is my ultimate Chicago experience.

For example, there was an episode when J.J. painted his version of Jesus, for which Ned the Wino was the model. Other than Florida (the mother), the household began falling into good fortune, and it seemed to be because they were praying to the painting. Florida, however, a true religious follower, thought it wrong.

There was the episode when J.J. was being recruited by a local gang. The father, James Evans, Sr., stepped in and kept the Evans family intact.

The greatest episode—yet nearly the saddest and most traumatic—is when James Sr. was killed in a car accident while out of town. The Evans family was in the middle of throwing a going-away party to celebrate the remerging of their family; they were scheduled to join their father and husband in their new home in Mississippi. However, when letters were read at the party, a telegram arrived with the news about James Evans, Sr. J.J.’s and Thelma’s and Michael’s father had died…my father had died. Every Black child’s—and probably some white ones as well—father had passed on that day. And when Florida’s defenses were down—finally—she uttered the most powerful three-word sentence in the history of television: “Damn…damn…damn!”

When I run across someone else who was/is a fan of “Good Times” and they’re knowledgeable about these and other scenes, episodes, and the feelings, it is easily one of the greatest moments of my life. My Chicago Top Ten Favorite List cedes spots to these Good-Times moments.

-Recommended by Executive Assistant Patrick Edwards

MILLENNIUM PARK SUMMER MUSIC SERIES

One of my favorite things about Chicago is all of the free art and cultural events that take place, especially in the summer. The Millennium Park Summer Music Series is at the top of my list. Every Monday and Thursday throughout the summer at the Jay Pritzker Pavilion from 6:30 - 9:30 p.m. you can sit on the beautiful lawn, eat a picnic, drink a beer, and listen to great live music from all over the world. It feels like we’re all hanging out in Chicago’s backyard!

-Recommended by Director of Programs Amanda Jones

Jay Pritzker Pavilion

Millennium Park photo