Want To Experience Chicago Like A Local? Start With These Must-Visit Spots

I first fell in love with the idea of moving to Chicago 11 years ago, on a visit to the city while I was in college. Chicago sure has changed a lot since then, from its riverfront, which has transformed its grim industrial zone into a pedestrian's paradise, to now boasting 20 Michelin-starred restaurants. Having finally made the move to settle in the Windy City in 2024 and experiencing, on a daily basis, just how much there is to see and do, I'm becoming its biggest fan.

As someone who routinely travels to every corner of this metropolitan marvel — drawing on my experiences in the real estate industry — I've been making notes on neighborhoods I love, gathering recommendations for eateries to try, and visiting places of interest. Although there are way too many spots to check out and things to experience, here is my non-exhaustive list of places I haven't seen too many people obsess over, but for those who know them, they love them. 

These five spots are all located within Chicago, Illinois, proper. And although well known, they are not overwhelmingly popular among routine visitors to the Windy City. Chicago locals know about them because they're either institutions that have stood the test of time or have earned a reputation as places well worth a visit.

Lawrence and Broadway in Uptown is home to a favorite hangout spot of the infamous Chicago legend, Al Capone. The Green Mill — opened nearly 120 years ago and originally named Pop Morse's Roadhouse — is an institution of jazz and cabaret that has hosted legends such as Billie Holiday and Al Jolson. More recently, greats consistently gracing the stage at this storied venue include The Chicago Cellar Boys and Chris Foreman.

A no-frills ambience that remains true to a bygone era, the music is complemented with a layout featuring booths and first-come, first-served seating. Al Capone's favorite booth still sits smack-dab in the center of the space. The interiors are reminiscent of a style I can only describe as Art Deco meeting unapologetic nostalgia — a softly lit, high-energy room that is bold yet vaguely familiar. The waitstaff is friendly, but here's a tip: tip well. Here's another tip: don't talk during performances, or else you will get called out (I didn't, but a friend definitely did). Oh, and if you're sitting in a booth, don't go up to order at the bar. Someone will definitely come and help you get what you need.

A cash-only policy further cements The Green Mill's insistence on belonging to a time beyond the present. Don't worry, though, there is an ATM inside. Its hours range from 4 p.m. to 1:11 a.m. (yes, you read that correctly), Sundays through Thursdays; 4 p.m. to 2 a.m. on Fridays; and 1 p.m. to 2 a.m. on Saturdays. There's also a poetry slam on the third Sunday of every month.

If you like magic, get ready to cater to the inner child in you that is obsessed with a good time and hours of wonder. Some of the performers at the Chicago Magic Lounge are top entertainers at the height of their craft, including Justin Purcell, Abby Segal, and Al James. Once you enter through the "secret" entrance via the laundry on Clark and Winnemac in Andersonville — located in Chicago's "Little Sweden" – the interiors and dim lighting set the mood for a great time.

Table service is available throughout, and it's always a good idea to arrive before the time listed on your ticket so you can enjoy a couple of drinks, a plate or two of snacks, and prepare for the show. The Lounge offers an extensive drinks menu, including cocktails and wines, and a food menu featuring shareable portions of classics such as flatbreads, potato pancakes, and tenderloin sliders, among other items. There are also plenty of non-alcoholic options, including coffee and tea.

Although I highly recommend getting premium front-row tickets so you're as close to the performances as possible, you're bound to have a terrific time regardless of where you sit. If you attend the Performance Bar show, you'll basically be sitting at the bar watching the magic unfold. Depending on the type of show and how close you want to be to the action, tickets will range from $35 to $90 per person. The Chicago Magic Lounge is open from 5 p.m. to 11 p.m. Mondays through Wednesdays, from 5 p.m. to midnight on Thursdays, from 5 p.m. to 2 a.m. on Fridays and Saturdays, and from 3 p.m. to 11 p.m. on Sundays.

Chicago has some fantastic bars. You have Aba, known for its skyline views decorated in lush Mediterranean interiors, and there's also a personal favorite of mine: The Hi-Lo, located on the corner of California Avenue and Thomas Street. Although The Hi-Lo is not generally known for its extensive menu, what it lacks in food, it makes up for in atmosphere and layout. The establishment is separated by an inside and an outside seating area, and summertime is a vibe if you manage to snag a seat outside.

I got the impression that this spot was designed to position itself somewhere between a swanky cocktail bar in the heart of New Orleans and a secret neighborhood gem in South Goa. The Hi-Lo has delicious cocktails and classic bar beverages on its menu. The heavier bourbon-based Dolce Vita and the light and refreshing gin-based Cucumber Rickey are must-tries. The good people at this cocktail bar have perfected their experimentation with the use of masalas, or spices, and this shows up frequently on their list of both alcoholic and non-alcoholic beverages. 

The fact that I got to hang around with in-house pups who were roaming around eagerly pestering patrons for pets made for a very well-rounded afternoon. And if you're lucky, Chicago's favorite tamale guy, Claudio Velez, aka the "Tamale Guy," will put in an appearance so you can try some of his lip-smacking tamales between drinks. The establishment is open from 4 p.m. to 2 a.m. Mondays through Fridays, 3 p.m. to 3 a.m. on Saturdays, and from 3 p.m. to 2 a.m. on Sundays. Just know, though, that the outside area, which comes fully packed with bar seats and wrought-iron patio furniture, sometimes closes before the rest of the bar does.

Although not the biggest secret anymore, given the coverage it's received from local media outlets, the Chicago Secret River Show offers a fun day experience for locals and visitors alike, if outdoor music is something you're into. The pier beneath the Belmont Bridge in Avondale works as a makeshift stage for secret summer shows, featuring a number of different bands. The lineup changes every week, and the initiative is the brainchild of the "River King," Lawrence Tome.

You can catch the shows from the bridge or make your way down below. If you do have a kayak, though, floating it down the river offers you the chance to have the best seats in the house. You can sign up for updates on when the next Secret River Show will take place by visiting the artist's website. Tome's Facebook page also provides routine updates. Shows usually take place from late Spring or early Summer to the end of Fall, weather permitting.

Given that Chicago was recently named "The World's Most Beautiful City" in 2025, it should come as no surprise to anyone that it's home to vibrant neighborhoods full of great eats, cool shops, and lakefront vibes like Hyde Park and Logan Square. However, Chicago also has a spooky edge and is home to some magnificent cemeteries. Specifically, the Graceland Cemetery and Arboretum.

This is a 155-year-old cemetery that was designed by the renowned landscape architect Ossian Simonds and H.W.S. Cleveland, among others. The cemetery spans 119 acres and sits hugging Montrose to its north, Clark to its west, and Irving Park to its south. Famous Chicagoans resting here include Charles Wacker, John Jones, and Alan Pinkerton.

Graceland Cemetery offers anything but a morbid time to visitors, and I think it's a beautiful place to take a walk at any time of the year. However, it is especially magical during the summer and fall months, given the splendid greenery and change of colors later on in the year. You could walk around birdwatching or just take in the pastoral and Victorian-era architecture. Just be mindful of not disrespecting or disturbing mourners during your time there.