Nothing Better Than Summer in Chicago
Even Though I Travel the World, Why Do I Spend Part of Every Summer in Chicago?
Summer in Chicago is unsurpassed: walking along the beach in the sun gazing at Lake Michigan, dining outdoors on the bank of the Chicago River in view of amazing architecture, strolling Michigan Avenue with an ice cream cone and shopping bags, enjoying a concert by the Grant Park Orchestra at Millennium Park on a beautiful evening, visiting a world-class museum, and having the choice of so much good food.
Most people have a bond with the place they grew up, but I adore my hometown of Chicago. I must admit that I cannot handle cold and snow. In the summer, however, the Windy City beckons and I can’t resist. Here is why:
On The Shore of Lake Michigan
The Lakefront: Parks and Beaches
The 26-mile shoreline of Lake Michigan stretches across the east side of the city and is filled with parks and beaches. The Chicago Lakefront Trail extends for 18.5 miles as a paved path, with separate lanes for bikes and pedestrians. This offers a perfect place to enjoy the stunning Chicago skyline.
Buckingham Fountain
The Clarence Buckingham Memorial Fountain opened in 1927 in Grant Park. A water display shoots water 150 feet into the air every hour on the hour. As dusk sets, colored lights enhance the show.
27 Sandy Beaches
Beaches dot the lakefront, enabling easy access wherever you stay in the city. I have had a few arguments with East Coasters who can’t imagine the Lake Michigan shoreline as a good place to sunbathe. You may not be able to surf, but there are plenty of waves and soft sand to enjoy a sunny summer day.
North Avenue Beach and Oak Street Beach are the popular spots in the downtown area, with food options and restrooms. If you are driving, head to the parking lot at North Avenue Beach. If you are staying downtown, Oak Street Beach is easy to reach on foot or by bus.
Lincoln Park Zoo
My family didn’t travel much when I was a kid, but my fondest memories include a trip to the Lincoln Park Zoo every summer. The zoo is still free to enter and has updated its enclosures to provide a better environment for its animals. I still enjoy the fun seal enrichment demonstrations, close viewing of spectacular silverback gorillas, and marveling at the rhinos and polar bears.
One of my favorite walks in the world is the stroll along the lakefront from the zoo to Navy Pier on a warm, breezy day with the water stretching out to my left and the skyline towering to my right. Pause at Oak Street Beach for a rest and a cocktail.
Navy Pier
I will admit that my main reason for going to Navy Pier is usually to take in the views of the incredible Chicago skyline or watch fireworks. However, millions of visitors each year enjoy the many restaurants, the food court, musical entertainment, shops, and a 150-foot-tall Ferris wheel. This is also a launching spot for tour boats and dinner cruises.
First designed by Danial Burnham in the early 1900s as part of the lakefront plan, the pier underwent an elaborate renovation in the 1990s to its current form.
Renting a bike near the pier enables you to explore the 18 miles of paved paths that provide wonderful views of the lake and skyline.
Book your bicycle tour by clicking here
The Heart of the City
Chicago River
The Loop and the North Side lie on either side of the Chicago River. Yes, Chicago has a beautiful lake and a vital river. Every cross street includes a bridge for cars and pedestrians that can be raised for the passage of tall boats. Nothing feels more iconic than watching “L” cars rumble over the river.
The Chicago River offers a wonderful setting for gazing up at the city’s stunning architecture. Two of my favorites demonstrate the range of styles and technology: the 101-story St. Regis, completed in 2021 by architect Jeanne Gang as the tallest building in the world designed by a woman, and the Wrigley Building, built in 1924 by the chewing gum magnate who also built the home of the best team in baseball.
Riverwalk
The walkway along the Chicago River, extending for over a mile from the lakefront, offers another lovely way to appreciate the city’s architecture. Several restaurants and bars have a wonderful vantage point.
River Cruise
The architectural cruises along the river remain one of the few touristy offerings that I will indulge in repeatedly. I continue to learn something new about the history of my hometown on every trip. The tour guides’ corny jokes only add to the experience, continuing the second city’s legacy of humor.
Magnificent Mile
Even though I am not much of a shopper, the iconic stretch of Michigan Avenue north of the river earns its name. Many high-end retailers compete for the most enticing storefronts. Dozens of restaurants and bars also occupy this area.
The strip runs from the iconic structures of the Wrigley Building and Tribune Tower to the Chicago Water Tower, which survived the Great Fire of 1871. The 100-story building formerly known as the Hancock Tower offers an observation deck and bar on the 94th floor, with stunning views of the lake and the city.
Millennium Park
In the heart of downtown, the 24-acre Millennium Park includes playgrounds, flower gardens, sculptures, and the Jay Pritzker Pavilion 4000-seat concert venue with a great lawn.
The Crown Fountain combines art and an open space for splashing around on a hot day. Cloud Gate, affectionately known as “The Bean”, reflects the skyline and the visitors posing for photos. The McCormick Tribune Plaza converts into an outdoor restaurant for the season.
The Loop
The Loop encompasses the area bound by the elevated trains, known as the “L”, that run on all four sides. This contains City Hall, where I worked for two summers at the Mayor’s Office of Special Events, and the Illinois State Building, featured in the 1986 movie Running Scared. These buildings show the range of Chicago architecture, as well as the Daley Center across the street. This plaza contains a 50-foot-tall steel sculpture designed by Picasso, the setting for noon-time performers every day.
State Street no longer has the landmark Carson and Marshall Field’s department stores of my youth, but it still offers shopping as well as the legendary Chicago Theater. Stop in one of the ubiquitous Garrett Popcorn stores to buy some of the best caramel corn you will ever taste.
Willis Tower
It took me many years to stop calling this the Sears Tower, and many people still can’t break the habit. Built in 1973 as the world’s tallest building, it held that title for 26 years. It was sold and renamed the Willis Tower in 2009.
Check out the fun Chicago museum before riding the elevator up to the Skydeck for an expansive view of the city. The Ledge allows you to step out onto a glass floor and peer down 103 stories at the tiny cars and people below.
Museums for Every Interest
Chicago offers so many museums that a visitor could spend the entire summer here exploring one each day. Many concentrate in the downtown area, and others are spread throughout the city. The following are my favorites and worth visiting, especially if you find yourself with a rainy afternoon and looking for something indoors to do.
Art Institute of Chicago
Whenever I travel, I seek out an art museum and have visited many prominent ones in Europe and the United States. The Art Institute ranks among the best in my eyes. It spans the art world from Roman artifacts to contemporary artists, from sculpture to multi-media works. All in a well-planned space, which is not as overwhelming as many famous museums.
Field Museum
The World’s Columbian Exhibition in 1893, held in Chicago, included a popular exhibit of natural wonders and cultural artifacts. Marshall Field donated one million dollars to create a permanent collection, which has grown to over 40 million objects today. The white marble building with classical columns that now sits on the lakefront museum campus opened in 1921.
As a child, I loved the taxidermy dioramas of animals, the dinosaur skeletons, and the ancient Egypt displays. I still enjoy these, but my new favorite is the completely renovated gallery, Native Truths: Our Voices, Our Stories. The Field Museum collaborated with Native scholars, artists, and community members to design the exhibit. It includes many interesting personal stories.
Shedd Aquarium
Originally designed to resemble a Greek temple, the Shedd Aquarium also features a neoclassical architecture, though with an octagonal layout. Its main founder, John G. Shedd, was also connected to the Marshall Field company as its president. Two major expansions of the museum maintained the historical original building.
The main exhibits highlight tropical fish, sharks and reef dwellers, and a walk along the Amazon River. Visitors can also see plenty of mammals, including otters, dolphins, beluga whales, and sea lions. Don’t miss watching the penguins or touching the stingrays.
Frank Lloyd Wright Home and Studio
Those with a passion for architecture should not miss traveling to Oak Park, a suburb on the west side of the city, to visit the Frank Lloyd Wright Home and Studio. When Wright started his own architectural firm, he chose a site in this emerging community to showcase his talents.
He completed his home and office in 1889 and designed many of the nearby houses. The tour explains Wright’s history and working style, as well as the intricate details he placed into every living and working space.
Choose a walking tour that brings you past the houses that Wright designed for his clients nearby on Forest and Chicago Avenues. These range from wood-framed bungalows to vast stone mansions. They showcase the iconic elements he developed, such as incorporating the surrounding nature, concealing the entrance door, and placing chimneys centrally.
For a tour departing downtown Chicago and bringing you to Oak Park and two other locations, click here
Make it a full day in Oak Park by also visiting the Unity Temple, designed by Wright, Ernest Hemingway’s Birthplace Museum, and the shops and restaurants on Marion Street.
From downtown Chicago, take the green line of the elevated train to Harlem and Lake Street and walk 0.7 miles to the FLW Home.
Best Summer Spots in the Greater Chicago Area
The Chicago area offers a few other attractions that make it worth renting a car for at least a day or two.
Garfield Conservatory
On the west side of the city, Garfield Conservatory offers an oasis of beautiful flowers and foliage within expansive glass greenhouses and 10 acres of outdoor gardens. The Conservatory was built in 1908 and revitalized in the 1990s.
The garden is easy to reach from downtown by car or by taking the Green Line “L” to the Conservatory-Central Park Drive stop.
Brookfield Zoo
The Brookfield Zoo offers two dozen habitats with animals from around the world. The park is spread out, which entails a good amount of walking to see it all. However, that also spreads out the crowd so visitors can get a good view of the animals. With many indoor and outdoor enclosures, the zoo is enjoyable whatever the weather.
The zoo is about 15 miles west of downtown Chicago and easy to reach by driving up I55.
Morton Arboretum
With 1700 acres of forest and meadows, the Morton Arboretum offers the perfect place to take a break from the bustling city. Stop into the visitor center to help plan your time there. Small parking lots throughout the park let you explore more of the space.
My favorite areas are the Meadow Lake, Woodland Trail, and Bur Reed Marsh. My certification for being a forest bathing guide required a three-day immersion in nature, and I chose the Morton Arboretum for my experience. It was very easy to connect with the natural world among the trees and flowers here.
The arboretum usually features an art exhibition of large-scale sculptures in various spots. It also conducts important research to help the conservation of and education about trees.
The garden is located about 25 miles from downtown, west on I-290 and I-88. You can save a little money on admission by purchasing tickets online in advance here.
Chicago Botanical Garden
When I travel, I love visiting local botanical gardens. The Chicago Botanical Garden is still one of my favorites and is worth the trip to the city’s north side.
With over 30 gardens and natural areas spread across 385 acres, the garden offers a wide variety in flowers, plants, and trees. My can’t-miss spots include the Japanese Garden, English Walled Garden, and Rose Garden.
Where to Stay
Chicago is a city of neighborhoods and offers many lodging options. You can stay in the heart of the bustle or choose a quiet residential area.
Downtown
Staying inside the Loop keeps you close to Millennium Park, The Art Institute, and the Chicago Theater. Grab an “L” to get to the airport or to other parts of the city.
River North/Magnificent Mile
If you want to be near the lakefront, the river, and Navy Pier, find a hotel in River North or along the Magnificent Mile of Michigan Avenue. There are many bars and restaurants in this area.
For a bit of a splurge, book an apartment with a fabulous view at Level Hotels & Furnished Suites.
North Side
For a more residential neighborhood and an easy trip to catch a Cubs game at Wrigley Field, stay on the North side of the city within walking distance of one of the beaches.
Hyde Park
The south side also offers easy access to the lakefront and beaches. Hyde Park is home to the University of Chicago, the Museum of Science and Industry, and the DuSable Black History Museum. The Obama Presidential Center is scheduled to open on June 19, 2026.
Oak Park
I lived in Oak Park for three years, so I may be a bit biased, but this is a wonderful, quiet area with nice restaurants and parks. I love walking around, looking at the beautiful houses and landscaping.
Evanston
Another place special to me is Evanston: the home of my alma mater, Northwestern University. A scenic lakefront, noble houses, and great cafes and restaurants await. The elevated Purple Line brings you into the city.
Where to eat
It is easy to find great places to eat wherever you are in Chicago. This article would go on forever if I started reviewing restaurants.
My first recommendation would be deep-dish pizza, either at a famous chain or a mom-and-pop place. Giordano’s or Gino’s East stuffed spinach is my go-to.
I also don’t feel like you can go wrong with Mexican food, especially at a cheap taco stand. For a snack, try an ice cream shop or Garrett’s Popcorn.
Conclusion
Truly, nothing beats summer in Chicago. A vacation in the Second City includes the lakefront, the Chicago River, your choice of zoos or gardens, many world-class museums, stunning architecture, and every type of food you can desire. Plan to spend at least a few days exploring this magnificently scenic and enchanting city.
