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Back in the day, Chicago, Illinois, was a stinky place. Onions growing on the banks of the Chicago River nailed its reputation in the early days. Its dominance as “Hog Butcher to the World” also didn’t help.
That was then. Today, Chicago received the 2023 Conde Nast Traveler Reader’s Choice Award for the Best Big City in the US. That was the first time any city had won for seven consecutive years in the 36-year history of the award. The reason becomes clear when you visit.
Exhaustion will overtake visitors trying to slip anywhere other than the downtown area into a visit to Chicago. We aren’t going to explore evening entertainment either. We’re going to focus on the sites available during the daytime because after trekking to many of them, you’re going to be spent in the evenings.
Be Entertained at the Historic Auditorium Theatre
However, if you want a taste of evening entertainment, you can get the ambiance by doing a behind-the-scenes tour of the Auditorium Theatre during the day.
Opened in 1889, the Auditorium Theatre is a venue that hosts concerts, musicals, performances and events. The Romanesque-style Auditorium Theatre follows Chicago’s history from the Great Chicago Fire and World’s Columbian Exposition of 1893, through the rock and roll era of the ’60s and ’70s still rolls into the present.
From opera to hip-hop, from political conventions to sporting events, the Auditorium Theatre has played a role in the lives of Chicago citizens for 130 years. That’s it for evening entertainment. Now to the vibrant downtown scene.
There are vast cultural opportunities, so we’ll focus on those with the widest appeal. We’ll start with the South Loop Neighborhood, where many attractions are within walking distance of each other.
Stroll Through Millennium Park
Millennium Park is one of the largest green roofs in the world. Built on top of a railroad yard, it’s three square blocks of open lakefront complete with a Ferris wheel, outdoor music pavilion and ice-skating rink.
The park is free. In addition, the Chicago Cultural Center’s Greeter Service offers free tours as well as guided tours of Lurie Garden. It may take 1 to 2 hours to cover the main highlights of the park, including Cloud Gate, Crown Fountain, Lurie Garden and Jay Pritzker Pavilion. However, take more time to explore the park’s sculptures, gardens and art installations.
Visit SUE at the Field Museum
Photo by Marcia McGreevy Lewis.
Celebrate nature by exploring the Field Museum, one of the world’s leading natural history museums. The Field has an all-ages appeal, from the littlest who enjoy pressing the buttons to hear bird sounds in the taxidermy halls to those drawn to inspect fossils.
When you enter the museum, one of its most famous residents–the largest dinosaur to walk the earth—greets you. And don’t miss SUE, the most complete T-Rex ever discovered. The Field Museum is home to 40 million artifacts and specimens. If you can’t find at least one that excites you, go somewhere else. Maybe an aquarium is more your style?
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Look Penguins in the Eye at Shedd Aquarium
The Shedd Aquarium holds about 32,000 animals, which will excite you. They’re alive. Look penguins in the eye as they fly through icy waters and hold onto your hat as sleek sharks cruise overhead.
The bluegills, stingrays, sea stars, sea otters and sturgeons are mesmerizing. Be sure to take time for a live show to view animals from around the world.
Get to Know Downtown Chicago On a Walking Tour
Next, let’s dive into the arts culture, starting the Chicago Architecture Center Walking Tour. It’s a quick introduction to Chicago’s imposing architecture. This 90-minute tour probes the city’s architectural history by viewing buildings from early skyscrapers to new high rises.
You’ll unearth the city’s early period on the Chicago River, its rebirth after the Great Chicago Fire of 1871 and its development into a commercial and cultural hub. Meander from the 1929 Chicago Motor Club to the 1989 NBC Tower.
Be Like Ferris Bueller and Visit The Art Institute
If The Art Institute of Chicago was inspiring enough for Ferris Bueller to visit it on his Day Off, chances are it will appeal to you too. You can follow in Ferris’s footsteps while visiting the museum’s best-known masterpieces.
Founded in 1879, the institute is one of the oldest and largest art museums in the United States. It also received Tripadvisor’s “Best of the Best” US attractions of 2023. Be ready to meander among 300,000 works ranging from the Byzantine Empire to contemporary American art.
I was most impressed by the impressionist collection, which features pieces from van Gogh, Monet, Cassatt, Seurat, and Renoir. Georgia O’Keeffe’s expansive collection, “My New Yorks,” was also on display when I was there recently.
See Chicago From the River On a Boat Tour
Photo by Marcia McGreevy Lewis
Warm breezes will waft over the river as you embark on the Chicago Architecture Center boat cruise to study the iconic buildings on the skyline.
A tour guide will point out the significant buildings on the Chicago River, from the Renaissance-inspired 1924 Wrigley Building to the sleek 2020 St. Regis.
You’ll see why it’s called “Skyscraper Canyon” and learn the history of buildings like 600 West, built in 1908 to become a warehouse for Montgomery Ward. Other former warehouses like the 1898 Fulton House are now condominiums.
Take a Tour of Chicago’s Golden Age
One more outing you might enjoy is the Historic Treasures of Chicago’s Golden Age tour. The tour features the architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s most memorable buildings: soaring skyscrapers, historic homes, magnificent churches, and glamorous hotels. All this only scratches the surface of Chicago’s architectural treasures.
Learn from the experts at the Chicago Architecture Center and discover the brilliant minds and incredible stories behind the city’s urban landscape.
More Sights to See
To throw in a few more excursions, you might want to consider the Chicago Crime Tour, which explores the true crime history of gangsters like Al Capone and John Dillinger.
You can also catch the contemporary art exhibition series at Driehaus Museum, go on the Frank Lloyd Wright Oak Park Tour or take the self-guided Oak Street Walking Tour. It’s considered part of the “Magnificent Mile,” and that’s worth exploring too. This vibrant, bustling area is home to upscale shops, deluxe fashion outlets, posh hotels and cool restaurants.
Where to Eat in Downtown Chicago
Restaurants—where do I start? There are many on the Riverwalk, and I had a luscious chicken sandwich at the Sheraton Grand Chicago Riverwalk’s Chicago Burger Company. Eataly presents an innovative alternative to that sandwich.
Eataly is a bustling three-story Italian marketplace featuring restaurants, a bakery, a cooking school, a fresh pasta market, a candy shop and a fresh vegetable stand.
The homemade salads, pizza and pastas are scrumptious. For more Italian cuisine, be prepared to devour mounds of pasta at Volare. It’s a great place for casual dining.
Other great options are Lizzie McNeill’s, Streeterville Social, Paris Baguette and The Northman Beer and Cider Garden.
Where to Stay in Downtown Chicago
There are plenty of accommodation options in downtown Chicago. Here are a few to check out:
Best Chicago Accommodation Options
- Sheraton Grand Chicago Riverwalk
- Loews Chicago Hotel
- Embassy Suites by Hilton
- Intercontinental Chicago Magnificent Mile
- The Gwen by Mariott
- Hyatt Regency Chicago
Mark Twain said, “She’s never the Chicago you’ll see when you pass by the next time.” So, get there now for soooo much to see . . . and the Chicago White Sox might be playing . . . and you’ll want to see the Alder Planetarium . . . and the Lincoln Park Zoo . . . get started!
Author Bio: Marcia McGreevy Lewis (she/her) lives in Seattle and is a retired feature writer for a Washington newspaper. She has written for literary journals, magazines, travel sites and books. Reach her on Facebook and Instagram: marcialewis25, Twitter: @McGreevyLewis and Linkedin: marcia-lewis. Clips: gravatar.com/profile/about Display name: mmcgreevylewis Show more
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