Hey, planning a trip to Chicago this week? You've picked a fantastic time! Late August in the Windy City means brilliant sunshine, comfortable lake breezes, and a city alive with outdoor adventures, incredible food, and vibrant cultural experiences. Get ready to explore like a local and soak up all the magic Chicago has to offer before summer officially fades!
The Chicago Riverwalk is your personal urban oasis, stretching along the south bank of the Chicago River from Lake Shore Drive to Lake Street. It's perfect for a leisurely walk, offering stunning views of the city's iconic architecture. You can grab a drink, enjoy public art installations, or simply watch the boats glide by.
Tip: Rent a kayak from Urban Kayaks for a unique, water-level perspective of the skyline – especially fun on a sunny afternoon!
Home to the famous 'Cloud Gate' (affectionately known as 'The Bean'), Millennium Park is an absolute must-see. You can snap reflective selfies, cool off at the interactive Crown Fountain, or simply relax on the Great Lawn in front of the stunning Jay Pritzker Pavilion.
Tip: Take a moment to wander through the beautiful Lurie Garden on the park's south side for a peaceful escape with diverse plant life.
One of the oldest zoos in the country, Lincoln Park Zoo is a true Chicago gem and completely free! Nestled within Lincoln Park, you can spend hours observing animals like gorillas, rhinos, and seals, all while enjoying the lush, well-maintained grounds and gardens.
Tip: Aim to visit in the morning when the animals are typically most active, and be sure to check out the daily feeding and training demonstrations.
This iconic lakeside destination offers something for everyone. Take a ride on the Centennial Wheel for panoramic views of the city and Lake Michigan, explore Pier Park, or simply enjoy the fresh lake breeze from one of the many benches.
Tip: If you're looking for a lively evening, check out Offshore Rooftop & Bar, reportedly the world's largest rooftop venue, for drinks with incredible lakefront and city views.
You can't come to Chicago without trying a slice (or three!) of its legendary deep-dish pizza. This week, make a pilgrimage to Lou Malnati's, a Chicago institution renowned for its buttery crust and rich, cheesy goodness, or try Pequod's for its unique caramelized crust.
Tip: Be prepared for a wait, especially during peak hours. Order an appetizer like their famous bruschetta while you wait for your pizza, which takes a while to bake!
With gorgeous late summer evenings, Chicago's rooftop bar scene is buzzing. Head to LH Rooftop at LondonHouse for stunning views of the Chicago River and Michigan Avenue, or Cindy's Rooftop at the Chicago Athletic Association Hotel overlooking Millennium Park and Lake Michigan.
Tip: Many rooftops offer excellent brunch options on weekends, perfect for starting your day with a scenic meal.
Forget ketchup! Experience a true Chicago-style hot dog 'dragged through the garden' with mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers, and a dash of celery salt, all on a poppy seed bun. Portillo's is a classic spot to try this iconic street food.
Tip: If you're feeling adventurous, pair your hot dog with an Italian beef sandwich, dipped in gravy for the ultimate Chicago experience.
The Chicago Riverwalk isn't just for strolling; it's also a fantastic dining destination. You can find everything from casual bites to full-service restaurants. City Winery's Riverwalk wine garden is a popular spot for wine and small plates with great views.
Tip: Many spots along the Riverwalk have seasonal outdoor seating, so it's the perfect time to enjoy alfresco dining by the water.
Chicago is the birthplace of electric blues and has a legendary jazz scene. This week, immerse yourself in the city's musical heritage at a classic venue like Buddy Guy's Legends or Kingston Mines, where you can hear incredible live performances. Expect soulful music and an electric atmosphere.
Tip: Most blues clubs have cover charges and a two-drink minimum, so be prepared, and stay late – the best sets often start after midnight!
For a more intimate and sophisticated evening, seek out one of Chicago's renowned speakeasy-style cocktail bars. The Violet Hour in Wicker Park, known for its handcrafted cocktails and strict house rules (no phones, no standing), offers a truly unique experience.
Tip: Reservations are often recommended, especially for popular spots, and be sure to check their specific entry requirements or hidden doors!
With comfortable evenings, Chicago's rooftop scene is perfect for a night out. Joy District and I|O Rooftop Lounge in River North are known for their lively party atmospheres, stunning city views, and DJ sets, making them great spots to dance the night away.
Tip: Dress codes can vary, so it's always a good idea to check the venue's website beforehand to ensure you're dressed appropriately.
One of the oldest and largest art museums in the U.S., the Art Institute boasts an incredible collection spanning thousands of years. You can spend a day here admiring masterpieces like Grant Wood's 'American Gothic,' Georges Seurat's 'A Sunday on La Grande Jatte,' and Edward Hopper's 'Nighthawks.'
Tip: Take advantage of their free guided tours to get an insider's perspective on the museum's highlights and hidden gems.
Journey through billions of years of natural history at the Field Museum, home to world-famous exhibits. Come face-to-face with 'SUE,' the most complete T. Rex skeleton ever found, and 'Máximo,' the towering titanosaur that greets you in the main hall.
Tip: Dedicate at least four hours to ensure you hit the highlights, and consider visiting early in the day to avoid the biggest crowds.
Known as 'The People's Palace,' the Chicago Cultural Center is an architectural masterpiece offering a wide array of free public events. Admire the stunning Tiffany glass dome, browse art exhibitions from local artists, and catch free music or dance performances.
Tip: Don't miss the free building tours offered on Thursdays and Fridays to learn about the building's fascinating history and architecture.
Chicago is renowned for its architecture, and the absolute best way to experience it is from the Chicago River. A guided architectural boat tour provides fascinating insights into the city's iconic skyscrapers and their history from a unique vantage point.
Tip: Book your tour in advance, especially during peak season, and try a sunset tour for truly spectacular views as the city lights up.
No trip to Chicago is complete without a selfie with 'The Bean'! This iconic sculpture reflects the stunning city skyline and is a fantastic (and free) spot for photos and people-watching. You can also splash around in the nearby Crown Fountain, an interactive art piece.
Tip: Go early in the morning to avoid the biggest crowds and capture some unobstructed shots of 'The Bean' reflecting the sunrise.
As mentioned, the Lincoln Park Zoo is completely free to enter and explore. It's a fantastic way to spend a few hours enjoying nature and seeing a wide variety of animals without spending a dime.
Tip: Pack a picnic to enjoy on the zoo grounds, saving money on food while enjoying the beautiful surroundings.
This magnificent building is often called 'the most beautiful building in Chicago' and offers free admission to all its exhibits, performances, and architectural splendor. Don't miss the world's largest Tiffany stained-glass dome in Preston Bradley Hall.
Tip: Check their online calendar for free concerts and art exhibitions happening this week – there's always something new to discover.
Enjoy miles of scenic pathway along the shore of Lake Michigan, perfect for walking, jogging, or biking. You'll get incredible views of the city skyline, numerous parks, and beautiful beaches. It’s a wonderful way to experience Chicago’s natural beauty without spending a cent.
Tip: Rent a Divvy bike for an hour or two to cover more ground and see different parts of the trail, from Lincoln Park to Hyde Park.
Beyond the stunning city views, the Riverwalk often features public art installations and quiet spots to relax. At night, don't miss 'Art on theMART,' large-scale digital art projections displayed on the Merchandise Mart building.
Tip: Look for the Bridgehouse Museum at the Michigan Avenue Bridge for an interesting, albeit small, peek into the river's history (note: there's an entry fee for the museum itself, but viewing from the outside is free).
The Shedd Aquarium is a world-class institution where families can explore aquatic life from around the globe. Marvel at beluga whales, sea otters, penguins, and a vibrant array of fish in immersive exhibits like the Wild Reef and Amazon Rising.
Tip: Consider purchasing tickets online in advance to save time and sometimes money, and arrive early to beat the crowds, especially on weekends.
This massive museum is a playground for curious minds of all ages. Kids will love the interactive exhibits, from descending into a replica coal mine and exploring a captured German U-505 submarine to marveling at a 40-foot tornado.
Tip: Plan your visit to include one of their 3D films for an extra immersive experience, but be aware they are an additional cost.
Navy Pier is a fantastic spot for families, featuring the iconic Centennial Wheel, classic amusement rides in Pier Park, and the Chicago Children's Museum. There are also frequent free events and public programs that cater to kids.
Tip: Grab a sweet treat from JoJo's ShakeBAR at Navy Pier, known for its ultimate milkshakes that are a hit with kids and adults alike.
Just east of Millennium Park, Maggie Daley Park is a wonderland for families. It features an incredible playground with climbing walls, slides, and mini-golf. It’s a perfect place for kids to burn off some energy with plenty of unique structures to explore.
Tip: Wear comfortable shoes for both kids and adults, as you'll want to explore every corner of this expansive and creative play space.
See what's happening in Chicago today