iconic Chicago River and surrounding buildings

You’ve Seen the Bean. Now Let Me Show You Chicago.

The places I’d send a friend who’s already done the big sights and wants to experience more of the city.

I have two friends coming to Chicago soon. They’ve been here before, they’re frequent travelers, and they’ve already done the Bean, Willis (Sears) Tower, the Art Institute, and the other big sights.

This time, they want good food, history, interesting neighborhoods, and places with a story. Basically, more of the Chicago that Chicagoans actually live in.

I’ve lived in Chicago for over 30 years, and this is the guide I’m giving them.

 A quick disclaimer: This is NOT meant to be a definitive “Best of Chicago” list.

These are simply places I love, things I actually do, and the little tips I’d give a friend who asked me, “OK, I've done the tourist stuff. What should I do this time?”

Let's go.

Where to Stay:

If this is your second trip to Chicago, I’d get off Michigan Avenue and stay in one of the neighborhoods.

For a first visit, staying right in the center of everything makes sense. But once you know the city a little, we like to branch out. Gold Coast and Old Town are both good choices — still close to downtown and easy to get around, but you get more of a neighborhood feel.

We also tend to choose smaller, boutique-style hotels when we can. We like places with some personality, where you can actually get to know the people who work there.

A few I'd look at:

  • The Robey, Wicker Park: A true boutique hotel right in the middle of one of my favorite Chicago neighborhoods.
  • Viceroy Chicago, Gold Coast: This is a polished, full-service option, but still off Michigan Avenue and in a neighborhood.
  • SOPHY, Hyde Park: A little farther afield, near the University of Chicago, but an interesting choice if you want to experience a completely different part of Chicago.
  • The Sono, Old Town: Very small and more B&B-ish, in a great residential location.

Bucktown/Wicker Park Neighborhook

Also worth mentioning is Hotel Lincoln. It’s in a terrific neighborhood, very walkable and right across from Lincoln Park. It’s close to the lake, and Old Town is nearby. The hotel itself is a little dated in spots, so it wouldn’t be my first choice if having a newer, more polished room is important to you. But you can’t beat the location.

I wrote a whole article about exactly how we choose hotels, including location, what amenities actually matter to us, and what we don't care about at all. Read my exact hotel booking system here.

What to Eat:

Best Bakery

Mindy’s Bakery, Wicker Park

It’s not far from where I live, and I know the line starts forming before they open. Prepare to wait, but I promise you it’s worth it.

What to order:

Everything you order will be good. I’m completely serious. There aren’t many places I’d say that about, but Mindy’s is one of them, and Mindy Segal is a James Beard Award winner for a reason.

That said, my husband Edwards and I have favorites.

  • Twice-baked almond croissant - how do they even make it like that??? My eyes are rolling in the back of my head just thinking about it…
  • Hot fudge babka (Danish dough) - no words. And no one should speak when you eat it. It’s a religious experience
  • Smoked brisket & Swiss chard - this comes under the category of “sour cream dough tarts”, whatever that is. I never bothered to ask, I just eat ‘em.
  • Hot chocolate grand au lait - their signature drink made with rich, house-made hot chocolate ganache.
  • My friend Jane gets half decaf coffee / half hot chocolate - She swears by it and says they’re “really nice about it” and don’t even roll their eyes at her when she orders.

Insider Tip: There’s nowhere to sit and eat your treats, and I see people on the sidewalk leaning against a building, shivering (or sweating) while they eat. No bueno.

Here’s what to do instead (you didn't hear it from me):

Walk across the street to the other side of Milwaukee Ave. Go right on the corner at North Avenue to the Robey Hotel (you’ll see a Valet Parking sign - that’s the entrance). When you enter the Robey, the check-in area will be on your right. Don’t go that way. Stay straight into the hall and look for stairs on your left. Head up one flight and voilà! There are a few couches there by the windows to sit and enjoy your feast, and there’s a bathroom nearby as well.

Middle East Bakery and Grocery, Andersonville

Not your typical spot. It’s part bakery, part grocery, all delicious. It’s been an Andersonville staple since 1981, selling Middle Eastern, Turkish, and Persian foods.

What to buy:

  • Roasted garlic hummus
  • Goat cheese balls
  • Important! Mix these two together in one bite for an explosion of delight in your mouth. I’m not kidding.
  • Hand pies: there's a counter in the back (left as you walk in). Ask the guy for the best ones. He knows, and he’s honest! He turned me on to the Olive with Parsley & Cheese, and it’s unbelievable.
  • Turkish Delight: it’s handmade, and there are 15 different flavors to choose from! Pistachio baklava
  • Pita: it’s usually still warm sitting on the shelf, and it lasts for days in the fridge w/o getting stale.

Note: There’s a small restaurant attached to the market, but I’ve never eaten there because I love Taste of Lebanon so much. It’s across the street on Foster Ave. If you go, order the shawafel wrap and lentil soup (omg!) and don't miss the tabouleh. There are a few tables, and they are really, really friendly. You may want to skip their hummus, though. IMO, it’s not nearly as good as Middle East Bakery.

Restaurants

No shortage of great places to eat in Chicago, but here are a few I highly recommend.

1. La Luna Pilsen (Mexican, on Racine Ave)

Order the quesabirria! Three juicy shredded-beef quesadillas with pickled onion and cilantro, and the consommé for dipping is so smooth. The guac is very fresh and delish, and it has fresh pomegranate seeds on top. They have the best cocktail ever! It’s called the Mata Miel and something about this spicy mezcal margarita makes me crave it and think about it more often that I’d like to admit. Maybe the way the habanero flavor mixes with the pineapple? Don’t miss it.

Around the corner, it’s fun to grab a drink at Punch House, a basement bar inside Thalia Hall on 18th Street. Go early, when the place is pretty empty, and you can be mesmerized by the gigantic aquarium and 1970s paneling vibe for hours, undisturbed. Just sayin’...

Make an afternoon/evening out of Pilsen: Before dinner, go to the National Museum of Mexican Art. Admission is always free, and Pilsen is one of Chicago’s most interesting neighborhoods. Walk around Pilsen and check out the murals before heading to dinner.  

So, if you want the whole outing: National Museum of Mexican Art → Punch House → wander around Pilsen → La Luna.

Warning: parking gets very tight on weekend evenings, so go early or take a cab or rideshare.

2. Tanta in River North (Peruvian)

This place feels like a night out with a lively vibe, dark velvet booths, and beautiful decor. 

There’s a lot more going on here than just “Peruvian food.” The menu is inspired by different regions of Peru, as well as by the Japanese and Chinese influences that have become part of Peruvian cuisine.

Ceviche is a big deal here. Chef Jesus Delgado, born and raised in Peru, was the Cebiche Chef at La Mar. Eater says the ceviche tasting at Tanta “is the best way to sample the restaurant’s raw offerings; while it’s a financial commitment at $54, these are substantial bowls of raw fish.” 

The rooftop views are awesome and seasonal. So check before you go if that's part of your plan.

3. Mi Tocaya Antojería in Logan Square

If you want Mexican food outside the usual downtown restaurant circuit, this is where you should be. It’s in Logan Square, so it also gives you an excuse to spend time in another great Chicago neighborhood.

Also worth a stop: Bang Bang Pie in Logan Square. Go for breakfast, it’s delish and (obviously) get some pie.

Catch a movie: While you’re nearby, check out the Logan Theater, a neighborhood favorite with a $9 matinee, an Art Deco lounge with a full bar, and snack prices that won’t break the bank.

Hot Dogs

Superdawg

The #1 best place for a hot dog is, and always will be, on the far NW side of Chicago. 

Fun Fact: My husband, Edwards, and I celebrated our engagement there 22 years ago, on Labor Day. This year we were in London, if that gives you any idea how awesome the Dawg really is.;) In fact, Superdawg is listed in the book, “1,000 Places to See Before Die”. 


Superdawg shown in 1948

Look, I have a lot of respect for Gene’s and Jude’s, and have happily eaten my share of late-night Wiener’s Circle dogs. I’m not dissing any of the other places. But the Superdawg is different. In a class by itself. And for those of you who scour Reddit and hear that Portillo’s is the best for hot dogs, I heartily disagree. It’s mid at best. I honestly don’t understand why people like it so much.

When you go to Superdawg, here’s what you need to know:

  1. It’s a drive-in. You can also walk up and order in the small building.
  2. It’s far on the NW side of the city and is a great place to stop when you’re going to or from the airport, especially if you have a car.
  3. There are a few picnic tables next to the parking lot.
  4. There’s a great forest preserve across the street (on Devon) where you can eat outside and watch birds and stuff.
  5. The hot dog comes nestled cozily with warm french fries and a full pickle that seemingly floats on the side.
  6. Order it the way it comes. Do NOT freelance or think you know better about the balance of flavors. Do NOT mess with The Dawg.
  7. When you order, they’ll ask, “Do you want peppers?” Your choice, it’s good with or without the hot sport peppers. That part you can choose.
  8. It’s best to eat it right away. I wouldn’t take it to go, or you risk soggy fries, and you lose the unique steaminess of the entire experience.

Note: Chicagoans don’t put ketchup on their hot dogs, and they will shame you for doing so.


Frank's husband, Edwards, in front of Superdawg.

There are a bunch of theories about this, and I'm not going to pretend I know which one is true.

My favorite answer is this:

“Nobody really knows. I just know you'll be judged. Don’t embarrass me.”

Look, you can put ketchup on it. Just don’t tell anyone, OK?

Pizza

Lou Malnati’s deep dish cheese with Buttercrust

It’s a classic. Just good ol’ cheese. “The Lou” is also good if you’re in the mood, but I swear they use a different cheese on it.

If you’re inclined to say “it’s not pizza, it’s casserole,” I hear you. And you’re not wrong.

Deep dish is its own thing, so don’t expect “pizza” the way you’re used to. Our friend Ellen describes it as “cheese and tomato pot pie”. I wouldn't go that far (the crust is NOT like a pot pie!), but she has a point.

Also, Lou Malnati’s has very little actual “sauce,” but lots of tomato topping - more like chunks of real food than a sugary tomato sauce flavor. I love that about it.

The mozzarella is another part of what makes Lou’s great. They’ve sourced it from the same Wisconsin dairy for more than 40 years. 

Oh, and ordering Buttercrust is optional, highly recommended, and it’s a whole dollar extra. ;)

Music

The Green Mill, Uptown

This one’s on every Chicago list, and I'm including it anyway because it really IS that awesome.

When you enter, you immediately feel like you’re in a different era. And in this case, you pretty much have.

You can read about the Al Capone connection, the (alleged) Capone booth, and the trap door behind the bar leading to underground tunnels for a quick exit if needed. Who knows what’s really true? The spot was first known as Pop Morse's Roadhouse, a saloon founded in late 1898. Apparently, it was a popular spot for mourners from nearby Graceland Cemetery, which only adds to the lore and appeal of the place, if you ask me.

What you need to know before you go: 

  • There’s a great mix of age groups here. If you think you’re too old or too young for this jazz place, you’re not. 
  • They only take cash.
  • Drinks are cheaper than the average place IMO (bring cash).
  • On Fridays, the live music starts at 5 pm and goes for a few hours - no cover. Great for early birds.
  • Uptown is an urban environment, to state the obvious. Be mindful of where you park (you can sometimes find meters on Broadway) and make sure it’s well lit. Pay attention to your surroundings if you’re leaving the Green Mill late at night. Basically, don’t make yourself an easy target.


The Green Mill- Photo courtesy of Explore

Don't just go to the Green Mill. Make a night of it.

This is one of my favorite parts of this recommendation.

You're right by Argyle St., which means you have some terrific options for dinner before (or after) the music.

My top three:

  • Demera for Ethiopian.
  • Nhà Hàng Vietnam for authentic Vietnamese food.
  • Sun Wah for Hong Kong-style BBQ (winner of a James Beard “American Classics” award).

A walk around Argyle St. and the surrounding neighborhood, plus amazing ethnic food, plus the Green Mill for jazz - it’s a perfect experience.

That's a much better Chicago night than driving to the Green Mill, checking “historic jazz club” off your list, and driving back downtown.

Culture

History / Art / Museums…Here are 3 places that don’t get a lot of coverage in the media, but are well worth visiting.

1. National Museum of Mexican Art, Pilsen

This one fits perfectly with the Pilsen outing above. Admission is always free, and it's a chance to see Mexican art and culture while spending time in a neighborhood. 

Insider plan: Museum → walk around Pilsen and see the murals → Punch House → La Luna

2. The Driehaus Museum, near the Magnificent Mile

This is a good one if you're already going to be around Michigan Avenue and want something besides shopping and the usual tourist spots.

It’s inside the historic Nickerson Mansion, which is a gorgeous Gilded Age home built in 1879 and designed by Edward J. Burling to replace the original home that was destroyed by the Great Chicago Fire. The architecture and interiors of the building are just as interesting as the pieces in the museum’s collection. 

Insider tip: Don’t miss the view from the top floor. The view of the surrounding buildings is really special and offers a different perspective than I ever notice from the street level.

Also, Wednesdays from 4 to 7 are “Pay What You Wish”. Check the current schedule before you go to confirm. 

A nice neighborhood outing: The Driehaus Museum → Tanta for Peruvian food. I suggest you walk there (about 10 minutes) and see the architecture of the Medinah Temple and the former Chicago Historical Society building.

Medinah Temple and the former Chicago Historical Society building

When you leave the museum, walk south on Wabash to check out the Medinah Temple first. Then head west on Ontario to see the amazing structure at the corner of Dearborn and Ontario (The building is now a restaurant/nightclub, but it’s still gorgeous, plus…how thick are those outside walls?!? You gotta see it). Then continue your stroll to enjoy your feast at Tanta.

Tao restaurant/nightclub

If Gilded Age Chicago is your thing, put Glessner House on your list, too. It’s on Prairie Avenue, which was essentially Chicago’s version of Fifth Avenue when some of the city’s wealthiest families lived there. It gives you a completely different look at Chicago history than you’ll get downtown.

3. Wrightwood 659, Lincoln Park

Wrightwood 659 is an exhibit space that hosts rotating, special exhibits. It focuses on contemporary art and is generally only open during exhibits and mostly on weekends.

From the outside, this Lincoln Park building looks like any ordinary older Chicago building. Walk inside, and it’s all light and steel, concrete and brick. The interior was designed by Japanese architect Tadao Ando, and it does NOT disappoint.

You’ll want to get advance tickets on the website, and tickets are timed, so you can't just wander in whenever you feel like it. It’s in a quiet neighborhood on a tree-lined street, near Lincoln Park.

They offer “First Friday” and “Second Saturday” tours with a curator (you pay the usual admission fee), and those sell out quickly, so plan ahead if you want that experience.

Make a day of it: A great day would be Wrightwood 659 in the morning → lunch at The Brunchery on Clark St. (open from 9 - 3) → the Peggy Notebaert Nature Museum.

One more idea if you’ve already done Chicago’s famous architecture riverboat tour and couldn’t get enough, the Chicago Architecture Center offers walking tours that let you dig into individual neighborhoods, buildings, and parts of the city you may have missed from the river. Their tours are excellent. 

Are you coming to visit Chicago? Let us help! 

We’ll plan the perfect trip for YOU, based on your preferences, the focus of your trip, and who you’re traveling with.

You may be traveling with an elderly parent who needs special pacing and attention to mobility issues…

You might want to geek out at museums with an eye on spooky or gory stuff…

Or maybe you want a trip designed around architecture and history…

Whatever it is, we’ll find it for you. Save yourself hours of online searches and generic ChatGPT advice about “the hidden gems” that are trending on TikTok right now.

Today’s article was all about some of my favorite things in Chicago, but at Depth and Discovery Travels, we know every person is unique, and there are no cookie-cutter itineraries. Ever. We only focus on certain locations, ones that we know very well.

You can start with answering a few questions about what you like and don’t like. Click here to get started!


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