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NEW YORK DAWN™ > Blog > Real Estate > Issues to Do in Chicago This Weekend, From Locals
Issues to Do in Chicago This Weekend, From Locals
Real Estate

Issues to Do in Chicago This Weekend, From Locals

Last updated: February 26, 2025 9:43 pm
Editorial Board Published February 26, 2025
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The climate in Chicago is unpredictable, typically harsh, however you’re nonetheless asking your self what to do in Chicago this weekend. Chicagoans don’t let the temperature cease them from having a good time, and in the event you’re a customer, embrace the climate and keep it up. Chicago has its structure, museums, artwork, meals, and extra to supply for an unforgettable weekend getaway.

Irrespective of in the event you hire an residence in Chicago, are in search of a house close by, or hire, on this Redfin article, we’ve compiled skilled recommendation to take you thru the must-see sights, hidden gems, and engaging bites that can make sure you get essentially the most out of your weekend.

Uncover Chicago’s neighborhoods

Whereas Chicago’s iconic landmarks are a must-see, town’s neighborhoods supply equally fascinating experiences. Skip the standard vacationer spots and enterprise into areas like Hyde Park, the place historical past, tradition, and attraction come collectively in sudden methods. 

Shaka Mitchell co-founder of what was voted the very best fitness center in Chicago, Anthos Coaching Golf equipment, writes, “We’re biased however extremely suggest spending a day in Hyde Park. When it’s heat, head to Promontory Level, probably the greatest parks in Chicago, for a scenic run, stroll, or picnic with wonderful skyline views and the lakefront breeze. 

Within the winter, ice skating at Halfway Plaisance is a should. For brunch, deal with your self to a scrumptious, southern-style brunch at Daybreak A.M. Eatery after an lively morning. Fortunately, Hyde Park is house to some unimaginable museums, just like the Museum of Science and Business or the DuSable Museum, making it a straightforward subsequent cease. Finish your day at The Promontory; they at all times have one thing cool occurring, from comedy reveals and dance events to dwell music.” 

Dana Buccheri, a private coach at Robust With Dana, suggests exploration of the North Facet. 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 Health additionally recommends exploring the North Facet. His good day seems 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 group. 

Then, deal with your self to a specialty latte or ube matcha at Facet Observe Espresso. Spend the afternoon exploring femme-owned gems like Bon Femmes, Molasses, and Ponnopozz, earlier than indulging in genuine Neapolitan pizza at Spacca Napoli. In want of a nightcap? The Victor Bar’s acquired high quality cocktails in a classy, cozy lounge. Wrap up the weekend with a leisurely Sunday brunch at Bryn Mawr Breakfast Membership as a result of good meals and nice firm are what make Chicago really feel like house.”

Should-see artwork, museums, and experiences

Chicago is a metropolis filled with creative treasures, from world-class museums to galleries and immersive cultural experiences. As an artwork aficionado or just in search of a singular weekend exercise, town gives one thing for everybody. 

To start 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 each April at Navy Pier and showcases cutting-edge modern works from worldwide galleries and artists.

Terry Boyd of Blue Kitchen, a meals weblog notes, “Whereas the Griffin Museum of Science and Business is the museum most Chicagoans and guests affiliate with the South Facet, there’s a smaller, world-class, pay-what-you-wish museum the place we take company to wow them: The Institute for the Research of Historic Cultures (ISAC). Previously the Oriental Institute, it’s crammed with antiquities of North Africa and West Asia — 1,000 years of humanity underneath one roof, as their web site says. Egypt (together with, sure, mummies), Persia, Babylonia, Sumeria, and extra. 

Chef Lulu Duran of Cesar’s Killer Margaritas gives nice methods 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 Pictures & Cinema additionally recommends taking an structure 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 Pictures agrees with Ann stating, “As a Chicago native, I’ve a rising listing of issues that I like to do in my metropolis.  Primary is the Chicago Structure Boat Tour, at the same time as an area, I like to do that every year. 

The boat takes you on a surprising tour by way of all 3 branches of the Chicago River overlaying the historical past of Chicago’s structure and even some enjoyable information in regards to the Mob. Quantity 2 is a hidden gem – Cindy’s Rooftop Restaurant within the Chicago Athletic Affiliation Lodge. This rooftop restaurant overlooks Millennium Park and Lake Michigan for probably the greatest views within the metropolis. Lastly, I’d suggest going to a Cubs sport! There’s nothing like being at Wrigley Area on a pleasant summer season day and feeling the power of the followers cheering on their hometown staff.” 

Camera, shake, and fries on the table

Style the very best of Chicago

As you intend your weekend in Chicago, it’s at all times useful to listen to from the locals who know town greatest. Michael Scaletta from Windy Metropolis Sports activities Playing cards shares his good Chicago itinerary, filled 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 Pictures, provides, “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.”

Moreover, 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 Power & Conditioning recommends some shops to buy at, adopted by their favourite locations to seize a chunk. 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 & Pals Vegan Kitchen invitations 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.”

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