5 Chicago Restaurants My Family Tried and Loved, From French and Italian to Tacos and Chicago Classics

Chicago is known for its incredible food scene and on our recent family trip, we were fortunate to try restaurants at a variety of price points, thanks to recommendations from Choose Chicago, the city’s tourism board.

The good news? The food was fantastic. The bad news? I’m pretty sure I put on a few pounds in just four days. We ate a lot.

From a gorgeous French brasserie and a bustling Italian restaurant to a casual Rick Bayless spot where my son begged us to order more tacos, here are five Chicago restaurants we tried and what we thought of each one.

La Grande Boucherie

431 N. Dearborn Street, Chicago, IL 60654

We had lunch at La Grande Boucherie after spending some time around Millennium Park, which is only about a mile away.

The restaurant is beautiful. It’s an elegant French brasserie inspired by Belle Époque Paris, with soaring ceilings and an Art Nouveau-style interior. When we arrived for a late lunch so it wasn’t particularly busy.

We kept lunch fairly classic. The kids had ham and cheese baguettes with fries, while I ordered the Croque Madame, the classic French ham and cheese sandwich topped with an egg.

Of course, we couldn’t leave without dessert. That’s when we met chef Michael Taus. He’s a pastry chef who has also worked as a private chef for a number of celebrities. Naturally, I had to ask him which celebrities were the coolest to work for. His answer: David Bowie and his wife Iman. He also told me who wasn’t so cool, but I’ll keep that one to myself.

If you’re wondering why the restaurant wasn’t packed when we were there, apparently we were just early. We drove by a few hours later around dinner time and the place was hopping. Chef Taus told us they’d served around 450 dinners the previous night.

The Dearborn

145 N. Dearborn St., Chicago, IL 60602

The Dearborn is an urban American tavern in the heart of Chicago’s Loop and was perfectly located for our plans that evening. We had tickets to see & Juliet through Broadway In Chicago, which, by the way, was hilarious. But we were running late.

We arrived at The Dearborn around 6:20 p.m. and the restaurant was packed. The only table they could immediately offer us was in a bright, sunny spot, but we didn’t have time to wait for something else, so we took it.

Fortunately, we had one of the best waiters of our entire trip, which is exactly what you want when you’re trying to get a family fed and out the door in time for a show.

We were also still stuffed from lunch, so Natalie and I went relatively light and shared the burrata salad and Parker House rolls ($12). The kids kept things simple with a cheeseburger and grilled cheese.

The Dearborn is a great option if you’re seeing a show in the Theatre District since you can have dinner and then walk to many of the nearby theaters.

Olio e Più

445 N. Dearborn St., Chicago, IL 60654

Olio e Più is right next door to La Grande Boucherie in River North and across the street from RPM, where we ate on a previous Chicago trip.

The whole area was buzzing when we went for dinner. Both restaurants were hopping and there were tons of people out, including a noticeably young crowd.

Olio e Più is an Italian trattoria inspired by Southern Italy, with house-made pasta, Neapolitan-style pizzas, seafood and an energetic atmosphere.

The food and service were both excellent, but one of the highlights was the cacio e pepe, which was prepared tableside. I’m always a sucker for a little tableside theater, especially when the end result is a bowl of pasta covered in cheese and pepper.

One of my favorite endorsements of the restaurant, though, didn’t come from anyone working there. While we were outside, I overheard a woman walking down the street telling a visitor, “This is a great place to eat.” I have to agree.

Harry Caray’s Tavern at Navy Pier

700 E. Grand Ave., Chicago, IL 60611

You can’t visit Chicago without getting at least a little taste of the city’s legendary sports culture and Harry Caray’s Tavern at Navy Pier delivers plenty of it.

It’s located right on Navy Pier, next to Flyover, so it’s an easy lunch stop if you’re spending the day exploring one of Chicago’s most popular attractions.

For anyone who didn’t grow up watching baseball, Harry Caray was the legendary Chicago Cubs broadcaster famous for leading the crowd at Wrigley Field in singing Take Me Out to the Ball Game during the seventh-inning stretch.

The restaurant is filled with Chicago sports memorabilia, so there’s plenty to look at while you’re eating.

I ordered the Italian beef sandwich, which was huge. Natalie went with a Chicago hot dog, while the kids had grilled cheese with their choice of fries or carrots.

Between the location, the sports memorabilia and the classic Chicago food, Harry Caray’s is a fun stop, especially for families or baseball fans visiting Navy Pier.

Xoco

65 W. Illinois St., Chicago, IL 60654

Our most casual dinner of the trip ended up producing one of our kids’ favorite meals.

Xoco is chef Rick Bayless’ casual Mexican restaurant in River North, inspired by Mexican street food and markets. It’s not a fancy sit-down restaurant like some of the other places we visited. It’s relaxed, relatively inexpensive and they appeared to do brisk Uber Eats business while we were there.

First, get the agua fresca. The flavor changes and on the night we visited, it was raspberry lime. It was excellent.

I ordered the chicken tinga tacos, which I thought were very good, although our waiter kept encouraging us to try the beef or pork.

He knew what he was talking about. Natalie and Jack ordered the carnitas tacos and loved them. In fact, Jack declared Xoco his favorite meal of the trip and begged us to order more tacos. Fortunately, at just $8 for two tacos, giving in was an easy decision.

Jeni’s Splendid Ice Creams

Across the street from our hotel, the Sofitel Chicago Magnificent Mile, was an ice cream shop that had a line out the door every night. I wasn’t about to wait in a long line for ice cream, so I went back the next day when there were only a few people waiting to see what all the fuss was about. Jeni’s Splendid Ice Creams is known for its creative flavors and super-creamy texture.

They serve everything from classics like Salty Caramel to more adventurous seasonal creations, including a limited-edition Ted Lasso collaboration featuring crumbly shortbread cookies in buttery sweet cream. They’re generous with samples, so you can try a few flavors before deciding, and they use reusable silver spoons for sampling.

Instead of spending $7 on one scoop, I ordered the four-scoop flight with four spoons, which worked out to about a quarter of the price per scoop. Jeni’s has multiple locations in Chicago and across the U.S., and they ship their ice cream, too.

Chicago is a great city for eating

One of the things I love about Chicago is just how much variety there is when it comes to food. Over the course of a few days, we went from a beautiful Parisian-style brasserie to Italian food prepared tableside, a bustling downtown tavern, an iconic Chicago sports restaurant and a casual taco joint where our 10-year-old was ready to order round two before everyone else had finished eating.

And these were just five restaurants. If you want more recommendations, check out the four family-friendly Chicago restaurants we ate at during our last visit to the Windy City.

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