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My Chicago Restaurant Guide

Updated: Feb 24

Every couple has activities that are special to them. Some couples go golfing, some watch old films, some go camping. But my husband and I? We go out to restaurants. A lot. We are blessed to live in one of the best cities in the country for foodies. Bon Appetit Magazine has continually hailed Chicago as the “Best Restaurant City in America”, and I can’t agree more. Whether you’re after Italian, a steakhouse, a coffee shop or a famous Chicago hot dog I can promise you that you won’t go hungry. Even though our bank accounts aren’t always pleased with us, my husband and I are always planning our next meal out in the city. In the past 3.5 years since living here, we have created a list of some of our tried and true favorites. I’m so excited to share this restaurant highlight with you all to use next time you’re dining in Chicago, whether you’re a resident or just an occasional visitor! Bon appetit!


Basil Leaf:

I have to start out on a personal favorite of DeAndre and I’s. We first discovered Basil Leaf back when we were both still living in Michigan, but traveled to Chicago for a weekend to see if we wanted to move there. We stumbled across Basil Leaf when out exploring the city, and just so happened to move in to apartments right down the street from them. We can’t get enough of their low-key atmosphere and delicious Italian food. It is one of our favorite regulars.

What We Ordered: We always get the same thing every time, because its so tried and true! Cocktails & calamari to start, then our favorites: the angel hair with grilled chicken, tomatoes and basil; chicken piccata with linguine.

We What Loved: All of it. Every time.

What We Didn’t Love: Nothing. You can’t go wrong at Basil Leaf!

Summer House Santa Monica:

If you’re a Chicago resident, you know exactly what restaurant I’m talking about. Summer House is a very popular place to dine in the city, offering California-inspired dishes in a super cool airy atrium space. I have to say that I was also very impressed with their COVID protocols when we dined there in the pandemic. They also have an amazing in-house bakery, so save room for dessert!

What We Ordered: Homemade guac & chips to start, with cocktails (I LOVE their margaritas); Crispy Chicken Sandwich and Grilled Salmon for dinner; Homemade cookies for dessert!

What We Loved: I honestly think we can say we loved absolutely everything! Summer House makes delicious food and really generous portion sizes, so you definitely don’t leave hungry.

What We Didn’t Love: Service was bit slow when we went, but I know that is happening most places due to the labor shortage.

Photo from the restaurant’s Instagram account

The Dearborn:

The Dearborn is another long time favorite of DeAndre & I’s. It’s located right in the theatre district in the downtown Loop, so if you’re searching for a place to eat before or after seeing a show, I really recommend it! Their cocktails are super unique, and their menu offers upscale American but with a twist.

What We Ordered: Cocktails and their Parker house rolls (a must have!) & Midwest fried chicken to start; Fish n’ chips, The Dearborn Burger & for dinner.

What We Loved: Their cocktails are always amazing, and we love the food every time we go there.

What We Didn’t Love: Service was definitely slow, but also again that’s a lot of places most days. The Parker house rolls used to be a super delicious cheddar and chive, but they changed them to Everything But The Bagel. They were still good but not as amazing as the old ones.

Photo from the restaurant’s Instagram account

Morton’s Steakhouse

Although Morton’s is technically a chain, their original restaurant was founded in Downtown Chicago, right along the river. If you’re in the city and looking for a true steakhouse experience, I recommend Morton’s. You get a lot for your money, the atmosphere is laidback and romantic, and the waitstaff is really on their game. DeAndre and I didn’t know much about it before we tried it, and were pleasantly surprised!

What We Ordered: Cocktails & their Waygu Meatballs to start; Filet Mignon and Bone-In Ribeye, with grilled asparagus and lobster mac n’ cheese for dinner

What We Loved: Everything! The food was absolutely delicious, and portions were huge, and the service was impeccable.

What We Didn’t Love: The prices, haha! But in all honesty, we loved everything, but just be prepared to spend a bit more than you would at other places.

Photo from the restaurant’s Instagram account

A Few Honorable Mentions

Here are a few other favorites of mine, both casual and upscale:

  1. LUXBAR

  2. Mastro’s

  3. Steak 48

  4. Colectivo Coffee

  5. Francesca’s on Chestnut

  6. Yolk

  7. Tarascas

I hope this list brings you some food inspiration, and you can use it the next time you’re dining out in Chicago! And my biggest piece of advice is this: make a reservation. Now that COVID restrictions have started to lift and people are eager to get out, restaurants are packed. The OpenTable app is your best friend, trust me. But like I said, whether you’re on the hunt for some quick lunch to go, or want to enjoy a leisurely meal with your best friend, Chicago has everything you could want and more when it comes to food.

XO Meg

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