Chicago is an ideal destination for a long weekend cityscape. I have been to Chicago countless times and have cherished memories, including getting proposed to ( I did say yes!) and having a girls’ weekend bachelorette party during St. Patrick’s Day. Chicago’s diverse array of endless things to offer has fashion enthusiasts, food adventurers, and museum-goers flocking to this city. Below I have outlined the top places to see and do within a four-day trip to this beautiful city.
Please note that due to the ongoing pandemic situation, Chicago does have a vaccine mandate in place currently. This mandate is for those five years and older to access some indoor attractions, restaurants, bars, gyms, and other venues offering food and drink. Before heading to the city or specific interests, check the Covid entry requirements.
Where to Stay
Before I begin listing the top attractions in the city, picking a place to stay might be your first choice. My husband and I have visited Kimpton’s Hotel Monaco a few times when we have ventured to Chicago.
This hotel is one of our favorites because the hotel overlooks the Chicago River, so make sure you opt for a river view room. There is a complimentary wine hour in the lobby, is only two blocks off of Michigan Ave, and is close to the city transit “L” stop. Since my husband and I are light sleepers, experience has proven to avoid staying directly on Michigan Ave.
Staying directly on Michigan Ave tends to be noisier due to General Hospital being down the road. If the Kimpton Hotel is not for you, there are many great hotels and Airbnbs to stay in the area. My advice would be to find accommodations within the loop. Staying within the loop will allow you to be closer to restaurants and nightlife, especially if you don’t want to continuously take an Uber or walk long distances towards the end of the evening after strolling around the city all day.
Chicago’s Daytime Attractions
Home to countless well-known luxury and upscale retail stores worldwide, along with a diverse array of restaurants and hotels. Magnificent Mile is where you will come if you’re looking to spend some money on yourself and update your wardrobe while visiting the city.
Whether it’s the view you seek of Lake Michigan or a nice meal. Visiting John Hancock will allow you to take an elevator to the 94th floor to observe the city’s high rises and skyscrapers by heading to the 360 CHICAGO experience observation deck. Recently, a new attraction has gained popularity on the top of the John Hancock building called Tilt. Tilt allows you to extend outward over the Chicago skyline and get a vantage point facing downward just over 1,000 ft. Make sure to buy your tickets early to ensure a spot at this high thrilling attraction. Only eight guests at a time can venture out to view this one-of-a-kind experience. If you’re looking for a nice place to sit down, have a snack, or drink, my husband and I usually head to the lounge and grab a drink to take in the views. Don’t forget to grab a slice of cheesecake at the Cheesecake Factory before leaving on the lower level!
The iconic skyscraper gives people an adrenaline rush. If you have ever wanted to be bold and daring, this experience is for you! Towering at 103- stories, this sky deck allows people to walk out on a glass balcony taking in the views of the surrounding area all around you. Do you dare to look down at the bustling streets below your feet? Waiting lines tend to be rather long, so try to avoid going during peak times and purchase your tickets early. Tickets are based on a timed entry and must be present at such time for the line to the elevators. Due to the limited capacity, guests are allowed 30 minutes to explore.
Museums
The beauty of Chicago is the city’s many museums they offer. The Field Museum is great for those who love history. It has also been in the movie “Night at the Museum,” featuring the world’s largest Tyrannosaurus Rex display. The Museum of Science and Industry is a short drive down Lakeshore Drive. This museum is great for kids with the many hands-on child-friendly exhibits. It will leave the generation in awe and wonder. The Art Institute of Chicago is an expansive museum that has nearly 300,000 works of art from worldwide. One could get lost for hours in here. Some other ones to enjoy are visiting the Chicago History Museum, Adler Planetarium, Museum of Contemporary Arts, Museum of Contemporary Photography, Museum of Illusion, WNDR Museum, and many more. To look more in-depth at each museum, visit my Chicago’s Top Museums blog.
Journey to the depths of the sea and get immersed in this massive aquarium located on Lake Michigan. Opening its doors in 1930, Shedd Aquarium was the first inland aquarium that held a saltwater fish collection. Now the aquarium is home to approximately 32,000 beautiful animals. Get your tickets ahead of time to not miss out on this experience.
Millennium Park is home to Cloud Gate, also known as “The Bean. ” Many visitors tour this park to take photo opportunities next to “The Bean.” Due to the reflecting mirror and the structure’s shape, you might capture the beautiful Chicago Skyline if you stand in the right spot. Continuing your journey through Grant Park, you will reach the Buckingham Fountain. In the TV series “Married with Children,” the Buckingham fountain can be seen in the opening credits. It was also where my husband proposed, making this extra special for us. This fountain is romantic during the evening time, with the water changing vibrant colors. Be sure to add this to your list to check out.
One of Chicago’s top attractions with things to do for the whole family to enjoy. Many people venture to Navy Pier to take in the views of Lake Michigan and the Chicago city skyline from taking a ride on Chicago’s Iconic Ferris wheel the Centennial Wheel or just sitting on a bench overlooking the water can bring peacefulness as well. Kids will have fun enjoying all the activities Navy Pier has to offer. It will surely tire out the little ones between arcade games, funhouse mazes, and theme park rides. To plan a fun day at Navy Pier reserve your tickets early. Navy Pier is also the place to see fireworks that light up the skies in the summertime from Memorial Day to Labor Day. If you plan on walking to the pier from Millennium Park, it took us about 2 hours. However, we did stop and get a few drinks on the way.
Wrigley Field is home to the Chicago Cubs baseball team. The stadium is located on the Northside of Chicago and is easy to get to even if you don’t have an accessible vehicle. The CTA Red Line is a direct route from downtown Chicago to Wrigley Field. Shuttle buses or taxis/Uber will get you to where you need to be as well. If you visit Chicago in the summertime, be sure to see if the Chicago Cubs are playing. Even if you’re not into baseball, it’s fun to walk around and take in the iconic baseball field.
Day Cruises
Take a boat ride down Chicago’s river and learn about the city’s architecture. Cruises are great for everyone to enjoy, especially on a beautiful sunny day in the spring and summertime. Sit back, relax and take in another perspective on Chicago’s city life. Other options are a sunset cruise, dinner cruise, or even a tiki boat river cruise. There are so many options that everyone can enjoy.
If you plan on visiting more than one attraction while in town, be sure to check out Chicago’s CityPASS card. This card will allow you access to Shedd Aquarium, Skydeck Chicago, and the Field Museum. You will also get to pick two additional attractions of visiting either the Art Institute of Chicago, 360 Chicago Observation Deck, and or the Museum of Science and Industry. Purchasing your Chicago CityPASS will save you up to 50% savings off regular pricing.
Chicago Nightlife
Chicago has many things to do in the daytime, but what about the nighttime for us adults? Here are my top choices to visit for an enjoyable evening out with friends or loved ones.
Head over to The Second City if you’re looking for a fun night out filled with laughs and cherished memories. The Second City Theatre is known for Improv-Comedy. Since the pandemic, they have reopened to the public and will be performing new shows Thursdays- Sundays. The theatre is pretty distant from the Loop area, so opt for an Uber and show your support for these talented up-and-coming stars.
Website: www.secondcity.com
This beautiful exotic lounge creates an inviting tropical vibe. There are over 200 rums to choose from, small Polynesian-themed bites to eat, and stunning tiki drinks, some of which could be on fire. Three Dots and Dash is a spot that has everyone talking. Reserve a private room for your group for a special night out and relax in paradise.
Website: www.threedotschicago.com
Redhead Piano Bar is one of the best piano bars in town. The piano bar does not charge for cover, which is a nice change since most establishments do for the live entertainment portion. The vibe has been great when we have gone, and the drinks were good but can be on the expensive side depending on what you end up ordering.
Website: www.redheadpianobar.com
Step back in time and visit the Untitled Supper Club. The craft cocktails and the ambiance, which took on a prohibition-era design in the restaurant/lounge, made this restaurant unique with a one-of-a-kind experience. The performer’s acts can range anywhere from burlesque to circus aerial shows. Put this place on your list for an evening out for food, drinks, and entertainment with Chicago’s finest performers.
Website: www.untitledsupperclub.com
Get ready for the Instagram-worthy photos of Sugar Factory’s crazy drink concoctions and colorful menu options. You will get a visual overload with all the sweetness in one area as you enter the restaurant! The floor-to-ceiling displays of candy options for purchase will make anyone feel like a kid again. As you dine, everyone will have no trouble finding the perfect snack or meal with the assorted menu options that range from burgers to sandwiches and plates of pasta to grilled entrees. Treat yourself to one of Sugar Factory Signature Drinks! Between candy-style martinis, infused goblets, and beautifully crafted shakes, you are bound to leave with a sugar high. However, it will be so worth it!
Website: www.sugarfactory.com
Chicago Food Scene
Chicago is best known for the deep-dish pizza, the Italian beef sandwiches, and the Chicago-style hot dog; however, Chicago has much more. The Chicago steakhouses have been a thriving metropolis over the years, along with fine dining establishments, burger joints, Italian restaurants, and sandwich shops. The specialty snacks range from gourmet Garrett’s Popcorn to delicious cheesecakes. Check out my Chicago Food Scene Blog for a list of excellent top-notch restaurants in and throughout the Downtown Chicago area!
Overall Thoughts
Chicago has so much to offer for daytime and nightlife attractions. It’s what you make out of your weekend getaway that will be worth the memories! What is on your list when visiting?
