Things to Do in Chicago This Weekend, From Locals

The weather in Chicago is unpredictable, often harsh, but you’re still asking yourself what to do in Chicago this weekend. Chicagoans don’t let the temperature stop them from having a great time, and if you’re a visitor, embrace the weather and carry on. Chicago has its architecture, museums, art, food, and more to offer for an unforgettable weekend getaway.

No matter if you rent an apartment in Chicago, are looking for a home nearby, or rent, in this Redfin article, we have compiled expert advice to take you through the must-see sights, hidden gems, and tasty bites that will ensure you get the most out of your weekend.

Discover Chicago’s neighborhoods

While Chicago’s iconic landmarks are a must-see, the city’s neighborhoods offer equally captivating experiences. Skip the usual tourist spots and venture into areas like Hyde Park, where history, culture, and charm come together in unexpected ways. 

Shaka Mitchell co-founder of what was voted the best gym in Chicago, Anthos Training Clubs, writes, “We’re biased but highly recommend spending a day in Hyde Park. When it’s warm, head to Promontory Point, one of the best parks in Chicago, for a scenic run, walk, or picnic with amazing skyline views and the lakefront breeze. 

In the winter, ice skating at Midway Plaisance is a must. For brunch, treat yourself to a delicious, southern-style brunch at Dawn A.M. Eatery after an active morning. Luckily, Hyde Park is home to some incredible museums, like the Museum of Science and Industry or the DuSable Museum, making it an easy next stop. End your day at The Promontory; they always have something cool going on, from comedy shows and dance parties to live music.” 

Dana Buccheri, a personal trainer at Strong With Dana, suggests exploration of the North Side. Dana states, “I’ve lived in Uptown on the north side of Chicago for nearly 10 years. Here are some hidden gems I’ve enjoyed recently. The founder of Chicago, Jean Baptiste Point du Sable, was Haitian, and you can learn about the city’s roots and Haitian art, history, culture, and community at the Haitian American Museum of Chicago. Stop by Crema Shop nestled on Wilson Avenue for a sweet treat, a drink, and to enjoy the lovingly decorated ambiance. Qideas on Argyle is a nearby plant shop and a great spot to grab souvenirs for your stay while supporting a local business! Then, pop into Pho 888 across the street for the best pho in town. For a wardrobe refresh, get an affordable professional color analysis from Your Color Studio – a must-try experience.”

Greg Robbins Coach at Feast Fitness also recommends exploring the North Side. His perfect day looks like this: 

“Looking for the perfect weekend on Chicago’s North Side? Kick things off with a delicious Filipino-Cuban dinner at Bayan Ko, then sip craft spirits at Koval Distillery in the Ravenswood Corridor. Start your Saturday strong with a sweat session at Feast Fitness, voted the “Best Place to Unwind” by the Ravenswood community. 

Then, treat yourself to a specialty latte or ube matcha at Side Practice Coffee. Spend the afternoon exploring femme-owned gems like Bon Femmes, Molasses, and Ponnopozz, before indulging in authentic Neapolitan pizza at Spacca Napoli. In need of a nightcap? The Victor Bar’s got quality cocktails in a chic, cozy lounge. Wrap up the weekend with a leisurely Sunday brunch at Bryn Mawr Breakfast Club because good food and great company are what make Chicago feel like home.”

Deciding between renting or buying your next home? Explore your options.

Compare the costs of renting vs buying and find a lender to secure your mortgage.

Deciding between renting or buying your next home?

Compare the costs of renting vs buying and find a lender to secure your mortgage.

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 aficionado or simply looking for a unique weekend activity, the city offers something for everyone. 

To begin your Chicago exploration, Hummingbird Studios suggests, “We at Hummingbird Studios are avid art lovers and enthusiasts who enjoy visits to world-class museums and contemporary art galleries wherever we find ourselves. At home, The Art Institute of Chicago is our favorite cultural sanctuary where we can get lost for hours among the largest collection of cultivated works throughout world history. River North is home to many art and design galleries that host monthly events we like to frequent in the spring and summer. There is also our favorite event, the annual “Expo Chicago”, which takes place every April at Navy Pier and showcases cutting-edge contemporary works from international galleries and artists.

Terry Boyd of Blue Kitchen, a food blog notes, “While the Griffin Museum of Science and Industry is the museum most Chicagoans and visitors associate with the South Side, there’s a smaller, world-class, pay-what-you-wish museum where we take guests to wow them: The Institute for the Study of Ancient Cultures (ISAC). Formerly the Oriental Institute, it is filled with antiquities of North Africa and West Asia — 1,000 years of humanity under one roof, as their website says. Egypt (including, yes, mummies), Persia, Babylonia, Sumeria, and more. 

Chef Lulu Duran of Cesar’s Killer Margaritas provides great ways to spend a weekend in Chicago when he says, “For a cultural experience, the Museum of Science and Industry is a great option, and don’t miss their beautiful Japanese Gardens. Another favorite is the National Museum of Mexican Art, which offers insightful exhibitions and a shop with unique Mexican items. While Navy Pier and Lincoln Park Zoo are popular destinations for hidden gems, some of our favorite hidden gems are the Winter Garden on the top floor of the Harold Washington Library and the Bahai House of Worship, which has stunning gardens.”

Oksana of Oksana Kami Portraits says, “If you’re spending a weekend in Chicago, here’s what I’d recommend! First, definitely check out The Art Institute of Chicago — it’s one of my favorite museums, and you can’t miss seeing Van Gogh and Gauguin in person. After that, head to 360 Chicago at the Hancock Tower for some insane skyline views (and if you’re feeling brave, try Tilt—it’s a little terrifying but so worth it). If you’re up for it, a nighttime walk along the Chicago Riverwalk or a Chicago architecture boat tour at night is the perfect way to end the day. Chicago has so much to offer, but these are my absolute favorites!” 

Ann Oleinik from Ann & Kam Photography & Cinema also recommends taking an architecture tour, by saying, “Chicago is an amazing city, and there is so much more to do here than visit the Bean and eat pizza. First, take an Architectural boat tour where you will ride a boat on the Chicago River. A historian tells you about the city’s architecture and history, which is every guest’s favorite Chicago activity by far. If you want to explore the river on your own, you can rent a small boat or even a floating hot tub while you cruise up and down the river!” 

Photographer Lisa Kay Kovilic of Lisa Kay Photography agrees with Ann stating, “As a Chicago native, I have a growing list of things that I love to do in my city.  Number one is the Chicago Architecture Boat Tour, even as a local, I like to do this once a year. 

The boat takes you on a stunning tour through all 3 branches of the Chicago River covering the history of Chicago’s architecture and even some fun facts about the Mob. Number 2 is a hidden gem – Cindy’s Rooftop Restaurant in the Chicago Athletic Association Hotel. This rooftop restaurant overlooks Millennium Park and Lake Michigan for one of the best views in the city. Lastly, I would recommend going to a Cubs game! There is nothing like being at Wrigley Field on a nice summer day and feeling the energy of the fans cheering on their hometown team.” 

Taste the best of Chicago

As you plan your weekend in Chicago, it’s always helpful to hear from the locals who know the city best. Michael Scaletta from 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 a classic deep-dish pizza at Lou Malnati’s or Pequod’s — both are iconic. Stroll along the Riverwalk, where you can grab a drink at City Winery or take an architecture boat tour for some stunning skyline views. At night, head to Green Mill Cocktail Lounge for live jazz and a touch of old-school Chicago charm.”

Abby of Wren And Rose Photography, adds, “If you are looking for spots with ambiance, fantastic drinks, and great food I would highly recommend Best Intentions (for the burger lovers), Maple and Ash if you are looking for a meal worth every penny, and Gilt Bar the best ambiance and vibes.”

Additionally, Terry Boyd of Blue Kitchen recommends, “When you’re ready to eat, two area go-tos for us are the Hyde Park location of Small Cheval and Medici on 57th. The former is a tiny burger joint with generous outdoor seating, weather permitting, that serves up delicious burgers, some of the best fries you’ll find anywhere, and a selection of adult (and kid-friendly) beverages. Medici on 57th, a neighborhood staple for almost 60 years, serves pizza, sandwiches, breakfast, soups, and more in a funky, welcoming college town atmosphere.”

South Loop Strength & Conditioning recommends some stores to shop at, followed by their favorite places to grab a bite. They write, “I’d recommend stopping in a few record stores — Dusty Groove for funk, soul, jazz & Brazilian vinyl and Meteor Gem for heavy metal. Of course, there are a ton of amazing restaurants in Chicago as well. A few that stand out: Chicago Diplomat Cafe for Georgian (as in the Caucasus), Northern Taste for Northern Chinese food, and Denden for Eritrean.”Mun of Alice & Friends Vegan Kitchen invites you to “Explore Chicago’s Vegan Scene. Start your day with a plant-based feast at Alice & Friends Vegan Kitchen, where you can enjoy our signature dishes like Rainbow Rolls and Sweet & Sour Chi’kn. It’s a must-visit for food lovers! Fancy Plants in Boystown, Vegan Plate in Lincoln Park, and Bloom Kitchen in Bucktown are a must-visit. If you’re visiting in the summer, discover the local markets. Check out Green City Market for fresh produce and artisan goods. It’s a fantastic way to support local businesses and try unique flavors.”