15 Non Touristy Things to Do in Chicago (From a Local’s Perspective)

Chicago is one of those cities where you could visit ten times and still miss its quieter charms. Most visitors flock to the Bean, Navy Pier, and the Magnificent Mile but there’s a softer, more local side to the city if you know where to look. As someone who’s spent countless weekends exploring Chicago beyond the guidebooks, here are some of my favorite non touristy things to do in Chicago.

Whether you’re looking for cozy coffee spots, peaceful parks, or indie bookshops, this guide will help you experience the city like a local.

Where to Stay in Chicago (Away from the Crowds)

If you’re looking to skip the tourist traps and stay somewhere that actually feels like part of the city, here are my favorite non-touristy hotel picks in Chicago. Each one is nestled in a neighborhood I love  perfect for slow mornings, local cafés, and evening walks.

Sophy Hyde Park – Culture & Comfort Near the Lake

This boutique hotel in Hyde Park feels like a hidden retreat. It’s walking distance to the Museum of Science and Industry, the lakefront, and Promontory Point (my favorite sunset spot). The design is modern with artistic touches inspired by local writers and musicians.

Why I love it: It feels like staying in a stylish library-meets-loft space, with Hyde Park charm all around. Perfect for culture lovers and couples.

The Robey – Rooftop Views in Wicker Park

Located right at the crossroads of Wicker Park and Bucktown, The Robey is one of those places that blends cool design with real Chicago neighborhood vibes. You’re surrounded by boutiques, record stores, and indie coffee shops, with the Blue Line nearby for easy access downtown.

Why I love it: Their rooftop lounge, Up & Up, has amazing skyline views. I love waking up here and walking straight to brunch on Milwaukee Ave.

Publishing House Bed & Breakfast – Cozy and Artsy

If you want something truly personal and tucked away, this West Loop B&B is a gem. It’s inside a converted publishing house (hence the name) with 11 rooms, each named after a famous author. The vibe is intimate, stylish, and full of character.

Why I love it: The homemade breakfast, friendly hosts, and walkability to Fulton Market make this one of my favorite hidden stays.

Hotel Lincoln – Lincoln Park Vibes & Lake Views

Overlooking Lincoln Park Zoo and just a short walk from the Alfred Caldwell Lily Pool, this hotel feels like it’s tucked between city life and nature. The rooms are bright and quirky, and there’s a rooftop bar with lake and skyline views.

Why I love it: You can walk to the beach, kayak on the lake, or hang out in the park  then grab dinner at one of the neighborhood’s casual spots.

Ruby Room Inn & Spa – Quiet and Restful

Located in Wicker Park, this guesthouse and spa is a perfect pick for travelers who want peace and healing energy. No TVs, no noise  just beautiful rooms, aromatherapy, and a leafy garden patio.Why I love it: It feels like a wellness retreat in the middle of the city. Ideal for solo travelers or couples needing a reset.

Explore Local Neighborhoods (Like a Local Would)

Andersonville’s Swedish Roots and Indie Shops

Every time I wander through Andersonville, it feels like I’m visiting a small town tucked inside the big city. Located on Chicago’s North Side, this neighborhood has deep Swedish roots you’ll see it in the flag colors on street signs and the charming Swedish American Museum, which tells the story of immigrant life in Chicago through old photos, traditional costumes, and folk art.

But what I love most is how progressive and welcoming Andersonville feels. It’s a haven for the LGBTQ+ community and packed with independent businesses. Spend a Saturday browsing through vintage stores like Brown Elephant or unique home shops like Foursided.

Don’t leave without stopping at Women & Children First, one of the most beloved feminist bookstores in the country. I always end up buying more than I planned here and the staff picks are gold.

Local Tip: Grab brunch at Lost Larson (their cardamom buns are heavenly), then stroll down Clark Street with a coffee in hand.

Pilsen’s Street Art, Culture, and Soul Food

If you’re into colorful murals, authentic Mexican food, and creative energy, Pilsen should be at the top of your list. This neighborhood on the Lower West Side has become one of my favorite places to wander on a sunny afternoon.

The walls here tell stories, many tied to social justice, heritage, and identity. The 16th Street murals are a must-see outdoor gallery that changes frequently with new artists adding their touch. I’ve spent hours walking, stopping for photos, and soaking in the messages.

Hungry? Grab a plate of carnitas at Carnitas Uruapan (go early they sell out), or just follow your nose to a local tamale stand. For dessert, I usually head to La Michoacana Premium for a mango chamoy paleta.

Evenings are best spent catching a show at Thalia Hall, a beautifully restored 1892 opera house that now hosts indie concerts, comedy, and local events. I once saw a folk band there with string lights above and mezcal cocktails in hand it felt like a scene from a movie.

Local Tip: Visit the National Museum of Mexican Art (it’s free!) to understand the deeper cultural roots of Pilsen before exploring the streets.

Hidden Cafés and Quiet Hangouts (Where I Go to Slow Down)

The Understudy – Books, Coffee & Theater Vibes

The Understudy isn’t just a café it’s an experience. Located in Lakeview just steps from the Belmont stop, this space feels like a creative hideaway. It doubles as a bookstore and casual performance venue, and the vibe here is cozy-meets-eclectic.

The coffee is seriously good (their cortado is my go-to), but it’s the atmosphere that makes me linger. Walls lined with indie plays, comfy chairs, occasional live readings or monologue nights this place feels like it belongs in a Nora Ephron movie.

On quiet weekday afternoons, you’ll often find me here journaling by the window or chatting with strangers about Chicago theater life.

Local Tip: Check their Instagram for pop-up events and limited-edition zines by local artists.

Gaslight Coffee Roasters – Chill Meets Cool in Logan Square

Tucked on Milwaukee Avenue in Logan Square, Gaslight is equal parts café and neighborhood hangout. The first time I visited, I was drawn in by the old-school espresso machine and the smell of fresh roast but I stayed because it felt like a calm bubble away from the city noise.

There’s no rush here. People sip slowly, type away on novels, or sit outside on the wooden benches chatting about records or bike routes. The vibe is effortlessly cool without being pretentious.

The menu is short and curated think single-origin brews, flaky pastries, and a killer matcha latte if you’re not in the mood for espresso.

Local Tip: Come on a weekday morning if you want a quieter experience. Weekend brunch crowds tend to spill in, but it never loses its local charm.

Nature Without the Crowds (Chicago’s Quiet Green Escapes)

Promontory Point at Sunset

Promontory Point, tucked away in Burnham Park near 55th Street, is hands-down my favorite place to watch the sunset in Chicago. It’s located in Hyde Park, far from the tourist-heavy stretches of the lakefront, and feels like the kind of spot only locals know about.

The path curves through tall grasses and old stone steps, eventually leading to a rocky shoreline with open views of Lake Michigan and the skyline beyond. In summer, you’ll find people sunbathing, grilling, or just lying on blankets with books.

I usually come here late in the afternoon with a coffee or picnic, find a flat rock to sit on, and just let the waves drown out the city noise. It’s romantic, calming, and ideal if you need a breather from downtown chaos.

Local Tip: Bring snacks and stay past sunset. The view of the skyline lighting up is worth every mosquito bite.

Alfred Caldwell Lily Pool – A Secret Garden in Lincoln Park

The Lily Pool is one of Chicago’s best-kept nature secrets and I almost don’t want to share it. Nestled behind the Lincoln Park Conservatory, it’s a peaceful, landscaped haven designed in the Prairie School style. Think winding stone paths, trickling waterfalls, shaded benches, and wooden bridges arching over lily-filled waters.

I stumbled into it one summer while escaping the Lincoln Park Zoo crowds, and now it’s one of my go-to spots for solo walks or reading breaks. It feels like a portal into another world quiet, green, and full of hidden nooks where you can just sit and be.

The pool is also home to turtles, dragonflies, and birds, so it’s a favorite for urban nature lovers and photographers.

Local Tip: It’s free and open to the public, but has set hours (usually 7:30am–7pm). Go early for soft morning light and no crowds.

Culture, Music, and the Unexpected (Beyond the Big Stages)

Catch a Show at The Hideout

If you’re into live music with zero pretension and maximum soul, The Hideout is your place. This tiny bar and venue is literally tucked in between industrial warehouses in West Town, and it has one of the most intimate music scenes in the city.

It looks like a dive bar from the outside, but inside you’ll find everything from indie rock and folk to stand-up comedy and storytelling nights. The performers here are talented but raw often on the cusp of being discovered, or already cult favorites.

I once watched a local band play while the bartender handed out popcorn and people danced like no one was watching. It’s that kind of vibe.

Local Tip: Tickets sell out fast for bigger names, but the weeknight shows are often cheap or donation-based. Cash-only bar, so come prepared!

The Magic Parlour with Dennis Watkins

If you’re into old-world glamour and close-up magic, The Magic Parlour is unlike anything else in Chicago. It’s held in a historic private dining room at the Palmer House Hotel, and only 40 people attend each show which makes the experience super intimate and unforgettable.

Dennis Watkins, a third-generation magician, puts on a performance that blends sleight-of-hand, mind-reading, and storytelling. I honestly didn’t expect to enjoy it as much as I did but I was completely drawn in.

It’s sophisticated without being stuffy, and feels like something out of a 1920s Chicago speakeasy.

Local Tip: Dress up a little and grab a pre-show drink at Potter’s Lounge inside the Palmer House. It makes the whole evening feel extra special.

Eat Where the Locals Do (No Deep Dish Required)

Birrieria Zaragoza – Worth the Trip

This is hands-down one of the best meals I’ve had in Chicago and it’s nowhere near downtown. Birrieria Zaragoza is a family-run spot in Archer Heights, and it’s entirely focused on one thing: birria de res.

When I say they do one thing and do it exceptionally well, I mean it. The meat is slow-cooked until tender, served on housemade tortillas with consommé that’s rich, spicy, and addictive. Every table gets a basket of tortillas, lime wedges, salsa, and instructions on how to eat birria the “proper” way (they’ll gently walk you through it if you look lost, like I did the first time).

You’ll likely be the only tourist there, and that’s the beauty of it. No frills, no hype just phenomenal food that locals swear by.

Local Tip: They close by early afternoon or when they sell out. Go early (11am-ish) and come hungry.

90 Miles Cuban Café – A Party on Every Plate

Tucked away on Clybourn Avenue, 90 Miles Cuban Café brings the energy of Havana straight to Chicago. It’s BYOB, strung with fairy lights, and always buzzing whether you sit inside or on the patio, it feels like a celebration.

The ropa vieja is my go-to it’s slow-cooked, spiced, and melts in your mouth but honestly, you can’t go wrong with anything here. They also do brunch with Cuban coffee strong enough to power your whole day.

One night, I brought a bottle of rum, ordered a guava pastry for dessert, and stayed for hours chatting with strangers at the next table. That’s the kind of place 90 Miles is.

Local Tip: Bring your own wine or rum, and ask for a table on the patio during warm months. Don’t skip the maduros (sweet plantains)!

Relaxing and Slowing Down (Perfect for Solo Travelers or Sunday Mornings)

Browsing at Myopic Books

There’s something incredibly calming about getting lost in a used bookstore, and Myopic Books in Wicker Park is my favorite spot for it. It has three floors of floor-to-ceiling shelves, creaky wooden stairs, and that perfect old book smell.

The sections are loosely organized (which I secretly love), and it always feels like I’m on a treasure hunt. I’ve found vintage cookbooks, out-of-print plays, and handwritten notes tucked inside dog-eared novels.

The quiet upstairs reading loft has huge windows, and I’ve spent entire rainy afternoons here flipping through travel essays or poetry.

Local Tip: Bring cash if you can. Their card reader sometimes has issues, and prices are super affordable so it’s easy to walk out with a bag of books for under $20.

Chill at Humboldt Park Lagoon

Most tourists have never heard of Humboldt Park, which makes it one of my favorite green spaces in the city. The park is massive, located on the West Side, and has a totally different feel from Millennium or Grant Park it’s more relaxed, more diverse, and more community-oriented.

There’s a gorgeous lagoon with paddle boats, arched bridges, and even a boathouse that feels straight out of a Wes Anderson film. In the summer, you’ll find families barbecuing, teens playing soccer, and artists painting by the water.

I like to bring a picnic blanket, pick up an agua fresca from a street vendor, and just people-watch for hours.

Local Tip: Visit the Puerto Rican flag sculptures at the entrance they mark Paseo Boricua, a culturally rich strip of Division Street worth exploring too.

Bonus: Quirky and Unexpected Stops (If You Love the Unusual)

International Museum of Surgical Science

It sounds weird and it is but this museum is absolutely fascinating. Set in a historic Gold Coast mansion, the International Museum of Surgical Science walks you through centuries of medical history: old surgical instruments, medical illustrations, even a re-creation of an operating room from the 1800s.

It’s not crowded, very offbeat, and you’ll walk away with stories to tell (some mildly gross, some deeply moving). I once spent an entire afternoon here and barely saw five other people.

💡 Local Tip: It’s right near Lake Shore Drive, so pair it with a walk along the lakefront or a quiet lunch in the Gold Coast.

Green Mill Cocktail Lounge – Vintage Jazz Vibes

Stepping into Green Mill in Uptown is like time traveling. This cocktail lounge has been around since the Al Capone days literally, he used to hang out here and it hasn’t changed much since. The booths are velvet, the lighting is low, and the jazz? World-class.

It’s not just music either. They host spoken word nights, cabaret, and poetry slams that give the space a beautifully gritty, underground feel. I’ve come alone and with friends, and it always feels like a classic Chicago night out.

Local Tip: There’s often a line on weekends, and they don’t allow phones during performances. Come early, bring cash, and be present.

Montrose Point Bird Sanctuary – Hidden in Plain Sight

Right by the lake, just north of downtown, is a quiet haven filled with chirping birds and wildflowers: Montrose Point Bird Sanctuary, also known as “The Magic Hedge.” If you’re into nature, this spot is a dream.

It’s especially popular with birdwatchers during spring and fall migration, but I just love it for its peacefulness. A curved trail winds through prairie plants and leads to a sweeping lakefront lookout I’ve seen some of my favorite skyline photos taken from here.

Local Tip: Early mornings are best. Bring binoculars if you’re even a little curious about birding this place is full of surprises.

My Tips for Exploring Non-Touristy Chicago

• Ride the CTA buses instead of just the L trains way better for neighborhood hopping.
• Plan mornings in quieter spaces and evenings for music or food.
• Look for community events on neighborhood Facebook groups or local bulletin boards markets, pop-ups, and porch concerts are common in summer.

Conclusion: Skip the Bean, Find the Soul

Chicago’s magic doesn’t just live in its landmarks. It’s in a cup of coffee from a hidden café, the stillness of a lakeside trail, and the laughter echoing from a backyard jazz set. If you want to experience the Windy City like a friend is showing you around not like a tourist start with these spots. They’ve stayed with me long after the skyline faded from view.

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