The weather in Chicago is unpredictable and often harsh, but this weekend I’m asking myself what to do in Chicago. Chicagoans don’t let the temperature stop them from having a good time. If you’re a visitor, just hug the weather and continue. Chicago has architecture, museums, art, food and more that offer an unforgettable weekend getaway.
Whether you’re renting an apartment in Chicago, looking for a nearby home or looking for rent in this Redfin article, we’ve put together expert advice to show you the must-see tourist spots, hidden gems and delicious bites that will make the most of your weekend.
Discover Chicago neighborhoods
Chicago’s iconic landmarks are a must-see, but the city’s neighbourhoods offer an equally fascinating experience. Skip normal tourist attractions and challenge areas like Hyde Park where history, culture and charm come together in unexpected ways.
The co-founder of Shakamichel, who was named Chicago’s best gym at Antos Training Club, wrote: When it’s warm, head to Promontory Point, one of Chicago’s best parks, for a scenic run, walk or picnic with fantastic skyline views and the breezes of the lake front.
In winter, ice skating on the Midway Plays is a must. For brunch, after an active morning, then take yourself in a delicious South-style brunch at AM’s eatery at dawn. Fortunately, Hyde Park has several great museums, including the Science and Industry Museum and the Dusable Museum, and it’s the next stop. Finish the day at the cape. From comedy shows and dance parties to live music, they always do something cool. ”
Dana and Strong’s personal trainer Dana Buccheri suggests a northerly exploration. Dana said: “I lived in Uptown, north of Chicago for nearly a decade. Here are some hidden gems I have enjoyed recently. Chicago founder Jean Baptist Point du Sable was Haitian. You can learn about the city’s roots and Haitian art, history, culture and community at Chicago’s Haitian-American Museum. Stop by the Crema Shop on Wilson Avenue for sweet treats, drinks and enjoy the lovingly decorated atmosphere. Qideas in Argyle is a nearby plant store, a great place to grab souvenirs while supporting local businesses! Then pop across the street to Pho 888 for the best Pho in town. Get affordable professional color analysis from the Color Studio for wardrobe refreshment. A must-see experience.”
Coach Greg Robbins at Feast Fitness is also encouraged to explore the north. His perfect day looks like this:
“Are you looking for the perfect weekend in Chicago’s North Side? Kick out things at a delicious Filipino Cuban dinner in Bayanco and drink craft spirits at Cobal Distillery in Ravenswood Corridor. We started Saturday hard with a sweat at Feast Fitness and voted “the best place to relax” from the Ravenswood community.
Next, enjoy a specialist latte or Ube matcha with side practice coffee. Spend the afternoon and explore fem-owned gems such as Bonfem, Molasses and Ponnopoz before indulging in real Neapolitan pizza in Spaccanapoli. Do you need a night cap? Victor Bar has high quality cocktails in a chic and cozy lounge. Good food and great company make Chicago feel like home, so we close the weekend off with a Brynmer Breakfast Club on Sunday brunch. ”
Must see art, museums and experiences
Chicago is a city full of artistic treasures, from world-class museums to galleries and immersive cultural experiences. As an art lover, or simply looking for a unique weekend activity, the city offers something for everyone.
To begin your exploration of Chicago, Hummingbird Studios suggests: At home, the Chicago Museum of Art is our favorite cultural sanctuary, allowing you to get lost for hours in the largest collection of works grown throughout world history. River North has many art and design galleries that host monthly events that are frequented in spring and summer. Additionally, our favourite event, the annual Expo Chicago, held at Navy Pier every April, presents cutting-edge contemporary works by international galleries and artists.
Terryboyd of the Food Blog states, “The Griffin Science and Industry Museum is most Chicagoan and while visitors are related to the South, there is a small, world-class wife museum that pays small amounts of world-class salaries. It was previously an Oriental Institute, but was filled with ancient times in North Africa and West Asia. According to their website, one thousand years of humanity is under one roof: Egypt (yes, including mummies), Persia, Babylonian, Schmeria, and more.
Cesar’s killer margarita Chefrul Duran offers a great way to spend the weekend in Chicago. Another favorite is the National Museum of Art in Mexico. It offers an insightful exhibition and a shop with unique Mexican items. While the Navy Pier and the Lincoln Park Zoo are popular destinations for hidden gems, some of our favorite hidden gems are the Bahai Worship House, with the top floor of the Harold Washington Library and stunning gardens. ”
Oksana of Oksana Kami portraits said, “If you’re spending a weekend in Chicago, here’s what I recommend! First, check out the Chicago Art Institute. This is one of my favorite museums and you can’t miss out on seeing Gan Gogh and Gauguin meet in person. After that, head to 360 Chicago at Hancock Tower for an insane skyline view (it’s a bit scary if you feel brave, but it’s worth it). If you’re aiming for it, a night walk along the evening Chicago River Walk or Chicago Architectural Boat Tour is a great way to finish your day. There are so many things in Chicago, but these are my absolute favorites!”
Anne Oleinik of Anne & Cam Photography & Cinema said, “Chicago is a great city and there’s a lot more to do here than visiting beans and eating pizza. First, take a boat ride on the Chicago River. Historians will talk about the architecture and history of the city. This is the favorite Chicago activity of all guests. If you want to explore the river yourself, you can rent a small boat or a floating hot tub while cruising up and down the river!”
Lisa Kay Photography photographer Lisa Kay Covilic agrees with Anne. The number one is the Chicago Architectural Boat Tour. Even locals want to do this once a year.
This boat takes you on a stunning tour through all three branches of the Chicago River, covering some fun facts about the history of Chicago architecture and mob. Number 2 is the rooftop restaurant of Cindy, the Chicago Athletic Association Hotel. This rooftop restaurant overlooks Millennium Park and Lake Michigan and offers the best views of the city. Finally, I recommend going to the Cubs Game! I’m in Wrigley Field on a great summer day and don’t feel the energy that fans’ energy cheers on in my hometown team. ”
Enjoy the best Chicago
When you’re planning a weekend in Chicago, it’s always helpful to hear from locals who know the city best. Michael Scaletta of Windy City Sports Cards shares his perfect Chicago itinerary, packed with iconic spots and unforgettable experiences. He writes: “If you’re spending a weekend in Chicago, start with the classic deep-dish pizza from Lou Marnati and Pecod, both of which are iconic. A walk along the Riverwalk will allow you to drink at the City Winery or take an architectural boat tour for a stunning skyline view. In the evening, head to the Green Mill Cocktail Lounge for a touch of live jazz and an old-fashioned Chicago charm.”
Abby in the photo of Len and Bara said, “If you’re looking for a spot with atmosphere, great drinks and great food, I would recommend the best intentions (for burger lovers), maple and ashes.
Additionally, Terry Boyd of Blue Kitchen said, “When you’re ready to eat, it’s a place in 57 days of small Cheval and Medici Hyde Park. The former picks generous outdoor seating, a small burger joint that serves nice, delicious burgers, some of the best fries you can find anywhere, and some of the best adult (and child-friendly) drinks. A neighborhood staple for almost 60 years, Medici offers pizza, sandwiches, breakfast, soups and more.
South Loop Strength & Conditioning recommends several shops to shop, followed by your favorite spot to grab a bite. They write: “Dusty grooves for funk, soul, jazz & Brazilian vinyl, meteor gems for heavy metal – I recommend stopping at some record stores. Of course, there are plenty of great restaurants in Chicago too. Some stand out: Georgian’s Chicago diplomat cafe (like the Caucasus), tastes of Northern Chinese cuisine, Denden in Eritrea. Alice & Friends Vegan Start your day with a plant-based east feast at Kitchen. Enjoy signature dishes like rainbow rolls and sweet and sour chainan. It’s a must-see for food lovers! The flashy plants in Boystown, the vegan plates in Lincoln Park, and the Bloom Kitchen in Backtown are a must-see. If you’re visiting in the summer, discover the local market. For more information about fresh produce and artisanal products, check out Green City Market. A great way to support local businesses and try out unique flavors.”
