If you’re planning a trip to Chicago this summer, you’re in for a treat. With so much to see and do, it can feel a little overwhelming, but trust me, I’ve got you covered. From iconic tourist attractions like Millennium Park and Navy Pier to hidden gems like the Chicago Botanic Garden, the Windy City offers an unforgettable summer experience. And after a busy day of sightseeing, there’s nothing better than unwinding at one of the city’s incredible rooftop bars with a cocktail in hand, taking in the stunning views of the skyline.
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I’ve spent plenty of summers in Chicago, and over the years, I’ve developed a list of must-see spots that you absolutely can’t miss. Whether you’re a first-time visitor or a local looking for new things to do, this guide will help you craft the perfect summer day in the city.
Start Your Day with a Stroll through Millennium Park
No summer visit to Chicago is complete without a stop at Millennium Park. Located in the heart of downtown, Millennium Park is a sprawling green space that’s home to some of Chicago’s most iconic landmarks, including the famous Cloud Gate (also known as “The Bean”). If you haven’t seen it in person, trust me, it’s even more mesmerizing up close. Standing under the shiny, reflective surface, you’ll get a distorted view of the city that’s perfect for those Instagram-worthy shots.
But Millennium Park isn’t just about the Bean. You’ll also find the Jay Pritzker Pavilion, a stunning outdoor concert venue, and the beautiful Lurie Garden. In the summer, the park comes alive with outdoor concerts, theater performances, and special events, so check out the schedule before you go. I’ve attended a few of these concerts, and there’s nothing quite like listening to live music surrounded by the city’s skyline.
Wander Around Navy Pier
Next on your Chicago summer itinerary should be Navy Pier. This place is a bit of a tourist magnet, but for good reason. It offers a fantastic blend of entertainment, dining, and stunning views of Lake Michigan. Whether you want to ride the giant Ferris wheel, explore the interactive exhibits at the Chicago Children’s Museum, or just take a leisurely walk along the pier, it’s a great spot to spend a couple of hours.
I remember visiting Navy Pier on a warm summer evening and grabbing some fresh popcorn from one of the kiosks before sitting by the water to watch the boats glide by. It’s a perfect spot for a laid-back afternoon, and if you’re lucky, you might catch one of the weekly fireworks shows that light up the sky over the lake.
One thing to keep in mind is that while Navy Pier is undeniably a popular destination, it’s big enough to find quieter areas where you can relax and take in the beauty of Lake Michigan. And if you’re into boating, consider renting a kayak or taking a lake cruise to get a different perspective of the city’s skyline from the water.
Hidden Gem: The Chicago Botanic Garden
Now, let’s get to one of my favorite hidden gems in Chicago – The Chicago Botanic Garden. Located just north of the city in Glencoe, this serene oasis is often overlooked by tourists, which makes it even more special. With over 385 acres of gardens, nature trails, and lakes, it’s the perfect escape from the hustle and bustle of the city.
I visited the garden last summer and was absolutely blown away by its beauty. There are so many different themed gardens to explore, from the lush Japanese Garden to the vibrant Rose Garden. If you love flowers and plants, this place is a dream. Even if you’re not a gardener, it’s still worth the visit. The peaceful atmosphere is ideal for taking a slow walk, reading a book, or simply soaking in the natural beauty around you.
What I love most about the Botanic Garden is that it’s not just a place for relaxation – it’s also educational. The garden offers various seasonal events, educational programs, and gardening classes. Whether you’re an expert or a beginner, there’s always something new to learn.
Lunch at a Chicago Classic: Lou Malnati’s Pizzeria
By now, you’ve probably worked up an appetite, and there’s no better place to grab a bite than Lou Malnati’s for an authentic Chicago deep-dish pizza. Located in the Lincoln Park neighborhood, Lou Malnati’s is an institution when it comes to pizza. The crust is buttery and flaky, the cheese is rich and gooey, and the tomato sauce has just the right tanginess. It’s one of those things that you have to try when you’re in the city – and trust me, once you’ve had it, you’ll be hooked.
I always order the Malnati Chicago Classic, which features mozzarella cheese, Italian sausage, and the signature Lou Malnati’s tomato sauce. Don’t forget to pair it with a cold beer, and if you’re feeling adventurous, try one of their signature cocktails. It’s the perfect way to refuel before heading out for more adventures.
Afternoon: Take a Walk Along the Lakefront Trail
After indulging in some pizza, why not burn it off with a scenic walk along Chicago’s Lakefront Trail? This 18-mile path stretches along Lake Michigan, offering stunning views of both the water and the city skyline. It’s one of my favorite places to walk, run, or bike in the summer. The cool breeze coming off the lake, the sound of the waves lapping against the shore, and the view of the skyline make for an unforgettable experience.
Even if you’re not into biking or running, I highly recommend taking a leisurely stroll along the trail. You can stop at one of the many parks and beaches along the way to relax or even take a dip in the lake. If you’re feeling a bit adventurous, rent a bike or a tandem bike with a friend and make your way up and down the trail. Either way, it’s a peaceful and scenic way to spend part of your afternoon.
Hidden Gem: The Alfred Caldwell Lily Pool
While you’re at the Lakefront Trail, I have to share another hidden gem that’s just a short detour away from the trail – The Alfred Caldwell Lily Pool. Located in Lincoln Park, this tranquil oasis is a beautiful and often overlooked spot in the city. It’s a quiet, lush garden filled with water lilies, native plants, and a small pond. It’s the perfect place to escape the crowds and enjoy a little peace and quiet.
I stumbled upon this place a few summers ago when I was exploring the Lincoln Park area, and I was immediately taken by its charm. The architecture of the pool is also gorgeous, featuring a mix of Art Deco and Prairie styles. It’s a serene spot that feels worlds away from the busy city.
Cruise Through the City: Chicago River Architecture Boat Tour
No visit to Chicago in the summer is complete without hopping on a Chicago River Architecture Boat Tour. If there’s one touristy thing I’ll always recommend (and happily do over and over again), it’s this. I’ve done it multiple times, with family, friends visiting from out of town, even solo, and every single time, I walk away learning something new and falling more in love with the city.
The tour is a relaxing 60–90-minute cruise along the Chicago River, with a knowledgeable guide narrating the history behind the city’s most famous buildings. You’ll hear stories about the Great Chicago Fire, the rise of the skyscraper, and the city’s unique approach to urban planning. And let me tell you, even if you don’t consider yourself a history or architecture buff, it’s fascinating.
There’s something magical about floating down the river, surrounded by towering glass, steel, and stone, while the summer sun glints off the water. Plus, many of the boats have open-air decks, which means you’ll enjoy incredible photo ops and refreshing breezes the whole time.
Some even offer twilight or evening cruises, which are perfect if you’re looking to pair this with a sunset or pre-dinner experience. Imagine sipping a cocktail on deck while the city starts to glow, pure summer magic.
Pro tip: Book your tickets in advance, especially on weekends, because these tours fill up fast in peak season. And don’t forget your sunscreen!
End Your Day with Drinks at a Rooftop Bar
After an action-packed day of sightseeing, there’s no better way to wind down than with drinks at one of Chicago’s fantastic rooftop bars. Whether you’re in the mood for a craft cocktail or just want to enjoy a cold beer while taking in the city’s skyline, Chicago has a rooftop bar for every vibe.
Here are a few of my favorite rooftop spots:
- Cindy’s Rooftop: Located on the 13th floor of the Chicago Athletic Association, Cindy’s offers sweeping views of Millennium Park and Lake Michigan. It’s the perfect spot for an upscale drink with a view.
- The Aviary: If you’re looking for a more upscale experience, head to The Aviary in the West Loop. Known for its innovative cocktails, this rooftop bar offers a unique experience with expertly crafted drinks.
- The J. Parker: Situated atop the Hotel Lincoln in Lincoln Park, The J. Parker is a laid-back rooftop with great views of the city and Lake Michigan. It’s a fantastic spot to relax with a drink and watch the sunset.
- CloudBar at 360 CHICAGO: Perched 1,000 feet above the city at the top of the John Hancock Building, CloudBar gives you a drink with a side of wow. It’s part of the 360 CHICAGO observation deck, so while you sip on a cocktail or local beer, you’re also taking in jaw-dropping views that stretch across the skyline and Lake Michigan. I did this once on a clear evening, and the pinks and purples in the sky were unreal, totally worth the ride up.
A perfect summer day in Chicago is all about balancing the iconic attractions with the city’s hidden gems. From the reflective Cloud Gate to the serenity of the Chicago Botanic Garden, there’s no shortage of things to see and do. And of course, you can’t leave without enjoying the views from one of Chicago’s rooftop bars, where you can toast to a day well spent in this incredible city.
So, next time you’re in Chicago, be sure to follow this itinerary – it’s a perfect way to experience the best of what the city has to offer, whether you’re here for the first time or coming back for more.
With love,
Bri & Cat
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