My husband, Bill, and I were recently in Chicago for a week, celebrating our 7th wedding anniversary. We had an amazing time. Think of all of the offerings of New York City but in a friendlier, cleaner, more laid back environment.

That’s Chicago.

We believe in really celebrating each year of our marriage and travel to a new city each year to eat, explore, rest, and spend most of each day outdoors. We splurge in just about every way because we believe our relationship is worth it.

Our trip to Chicago was no exception.

We had beautiful weather (apparently, August is the time to go…not so much in February or one of the winter months). Most of the time when we travel, we go for less time or have other commitments like weddings to break up the trip. This time was the most like our honeymoon – seven days with just the two of us!

One of the things that surprised me most was that Chicago is one of the cleanest cities I’ve ever been to and one of the most beautiful.

There were flowers and parks at every turn! I felt like I was in a cute European city at times.

Dozens of people shared recommendations with us and we followed quite a few of them. I thought I’d put together a post with all of the places we ate, things we did, and where we stayed. If you are ever planning a trip to Chicago or know someone who is, you’ll have it all in one place!

Because of my dietary restrictions (no gluten or milk products), I could have been limited in Chicago – the city of deep dish pizza – but I’m happy to say we had lots of incredible meals that both of us enjoyed. Everywhere we went was accommodating and many places had gluten-free menus, so I didn’t feel the least bit deprived. Here’s the scoop on places to eat and fun things to do! Click on the red hyperlinked titles to go to each place’s website to learn more.

Where We Ate

Beatrix

The Scoop: With multiple locations throughout the city, this place is a solid pick for any meal, and it was our very first stop once we arrived. According to their website, Beatrix is a neighborhood coffeehouse, restaurant and meeting place in Chicago’s River North, Streeterville, and Fulton Market neighborhoods. The menu features healthy meets delicious options, and also includes an iconic coffee and pastry counter, including signature cookies and in-house bakery favorites. That was enough to sell us, so we went for lunch.

What We Ate: Bill had the Kennebec fries with crispy lemons and chilis and Dr. Bob’s turkey burger served with poached egg mayo and a quinoa & almond kale side salad. I wanted something simple, so I opted for the grilled chicken kebab served on top of English pea hummus with lemon vinaigrette and a cucumber salad. I could have eaten an entire bowl of the hummus. The flavors were on point. Visit their website here for menus and a list of their locations.

The Purple Pig

The Scoop: When one of my coworkers found out I was going on a trip to Chicago, without hesitating, she said: “You HAVE to go to The Purple Pig.” She had recently been and said the trip wouldn’t complete without a meal there. Another Facebook friend also recommended it, and even our Uber driver was jealous as he dropped us off because he hadn’t been in some time. Since opening in 2009, The Purple Pig has been named one of the “10 Best New Restaurants in America” by Bon Appétit magazine, showcasing the flavors of Italy, Greece and Spain. They don’t take reservations, so it’s best to go as early as possible because they’re pretty much always busy.

What We Ate: Despite its name, there are a bunch of vegetarian and seafood options available in addition to their signature trio of “cheese, swine and wine”. I had my eye on the octopus appetizer because it was so highly recommended, but we arrived so early that the chef hadn’t fully prepared all of that day’s octopus.

Womp womp. Bummer.

We started with an appetizer of shaved carrots with kumquats (a small citrus fruit) and spinach served on top of a tahini-based spread and sprinkled with pumpkin seeds and peanuts. The flavors and textures were out of this world amazing. We had another seasonal appetizer of mussels served with cauliflower, mushrooms, and rice, and Bill had the milk-braised pork shoulder (the best he’s had, he said).

Just as we were closing out our check, our waitress came up to us with a smile, “The octopus is ready!” We knew we had to try it, and OH MY GOODNESS are we glad we did! It was Bill’s first time eating octopus, and he devoured it along with me.

The grilled octopus was served with fingerling potatoes, green beans, and the best salsa verde I have ever had in my life. It was one of our top three dishes of the entire trip! Check out The Purple Pig’s menu and learn more here.

Hi-Vibe Superfood Juicery

The Scoop: After getting pretty stuffed the night before at The Purple Pig, we wanted something light to get the day started on the day of our anniversary, so we jogged to Hi-Vibe Juicery, which was about a mile from our hotel. I had stalked their website and knew they had a variety of elixirs, smoothies, juices, and broths that would nourish my body (and they’re all paleo and 100% organic, too!).

What We Drank: We started the day with a Kill Shot (camu camu berry, oil of oregano, echinacea, ginger, turmeric, black pepper, lemon, green apple) to get our immune system and digestion going. We also had one of the coconut and apple cider vinegar drinks (the name is escaping me!) to rehydrate.

I ordered a serving of their activated bone broth made with these nourishing and immune-boosting ingredients: 100% grass-raised beef + pastured chicken bone broth spiked with a signature blend of ginger, turmeric, apple cider vinegar, coconut cream, and sea salt, brain octane, MCT, oil of oregano, black pepper extract, cayenne, grass-fed butter, and dulse (seaweed). It was so full of flavor, and introducing a warm, healing liquid like that to your stomach first thing in the morning can really help rev up your digestive system to take on the day. I also stopped by their second location a few days later and grabbed the Mood Mylk, but I’d love to try their Shaman Shake and Golden Mylk. This place is one of the best juice and smoothie bars in Chicago. For more info and the full menu, click here.

Wildberry Pancakes & Cafe

The Scoop: Bill and I love breakfast food, so we wanted to go to a top-rated spot for brunch on our anniversary. What drew me to this place was the variety in the menu and the fact that they have gluten-free breakfast options. Apparently, the waits can run nearly 90 minutes on weekends, so get there early!

What We Ate: We had a delicious meal, and I was even able to have gluten-free pancakes (you wouldn’t even know they’re gluten-free!) as a side to my meal. I got the vegan breakfast hash served with hash browns, spinach, wild mushrooms, avocado and their homemade gluten-free veggie burger. I topped off the burger with an overeasy egg.

Bill had the Fresca omelet made with sundried tomatoes, provolone, basil and avocado. I had a bite, and it was delicious! He also got a side of their cinnamon roll pancakes, and both of our bellies were happy when we left. Here’s their full menu and website with locations.

Maple & Ash

The Scoop: We wavered between several options when deciding where to spend our anniversary dinner but ended up picking Maple & Ash because of their high reviews online. What an experience! From the photo booth (which included a GIF-maker!) on the first floor to the buzz and vibe of the main restaurant, we knew we’d made the right choice.

What We Ate: Everything! At least that’s what it felt like when we left 🙂 We were welcomed with a dish of blistered shishito peppers and radishes served with sea salt and chilled butter along with a welcome cocktail made with vodka, blood orange bitters, lemon juice, elderflower, and vermouth. I’m a bit of a teetotaler and usually get mocktails when we go out to eat, but this drink was one of the best I’ve ever had. It was so light and smooth that I ended up having two.

Dinner was over the top delicious and fun. Bobby was the best waiter and really made the meal special. We started with the roasted beet and shaved greens salad served with rosemary roasted almonds and ordered their signature fire-roasted seafood tour (YOU HAVE TO DO THIS), and it was divine. I had the halibut for my main course, and Bill had the Skuna Bay salmon. Despite how majorly stuffed we were, we had to say “yes” to the make your own sundae dessert bar. I opted for blueberry sorbet, and Bill had ice cream.

Girl and the Goat

The Scoop: Bill and I have been fans of the Bravo show, Top Chef, for years, so when a friend recommended this restaurant and we saw that Top Chef’s first female winner was in charge, we knew we had to go. Reservations are tough to get at this place, so I would suggest booking at least a month out or do what we did and stop by at the start of dinner service at around 5pm on a weekday. We were seated immediately and just had to be out by 6:30, which wasn’t hard.

What We Ate: Girl and the Goat is a small plates restaurant (think tapas-style), so we ordered a few different dishes to share before heading to see Hamilton in downtown Chicago. We started with the kohlrabi salad, which was served with fennel, evalon (on the side – this is cheese), toasted almonds, roasted shiitake mushrooms, and blueberries. It was a neat combination of flavors and textures but was a bit salty for me. We tried the roasted cauliflower served with pickled peppers, pine nuts, and mint and enjoyed that.

Our favorite dish was pan-roasted halibut served with marcona almond butter, white asparagus, blueberry nuoc cham (a Vietnamese dipping sauce), and beech mushrooms. The marcona almond butter was out of this world. We wanted to lick the bowl when we were finished. We also ordered the sautéed green beans topped with a fish sauce vinaigrette and crunchy cashews and the seared scallop & sausage summery succotash served with green harissa. This place is a must-stop dining spot on a trip to Chicago, so check it out!

Real Good Juice Co.

The Scoop: I love food puns, and this place was full of them (how about the Kal E. Kapowski Smoothie…Saved by the Bell, anyone?). For more punny names, check out their full menu here. According to their site, this is what they do: “We are a company that makes juices that are real good. Cold pressed juices, locally sourced and organic smoothies, salads, granola and other stuff.” I’m in.

What We Ate: We stopped by for a late lunch after our day at the spa (info below!) on our anniversary. We shared an order of their avocado toast served on gluten-free bread, and I had one of their elixirs. What really brought us there was the promise of dairy-free frozen yogurt (chocolate!). We shared a serving of that topped with chocolate avocado mousse (like this recipe on my blog) and cacao nibs, which I’ve written about here. We swung by again on another morning midway through a run to have a juice to start the day. I always look for less than 10 grams of sugar in juices and make sure they are cold-pressed. Check the label because a lot of “healthy” juices can be super high in sugar.

Wheat’s End Cafe

The Scoop: If you are gluten-free and miss things like biscuits, donuts, bread, muffins, and even bagels, Wheat’s End Cafe has you covered! The cafe is located in the Lakeview area of Chicago and is 100% gluten-free. In 2007, a friend of Wheat’s End co-owners Susan McMillan and Amelia Fonti was diagnosed with Celiac Disease. Soon after, Amelia learned that she, too, was gluten intolerant. They became aware of the growing unmet need for gluten-free food that did not compromise taste and texture.

What We Ate: We started with a warm cinnamon roll because who doesn’t love cinnamon rolls?? Bill ordered avocado toast with an overeasy egg on top and gobbled his up. I ordered the shakshuka pizza, which is basically eggs on a pizza (all dairy-free, too!), served with a vegan pesto sauce. I wanted to love it, but the crust was a little tough to cut through, and the cheese slid off pretty easily. The flavors were great, but I’d definitely order a biscuit, avocado toast, or a pumpkin donut next time since those were all highly rated…and more breakfast-like. The menu was so extensive, I’d definitely want to go back to try more!

Left Coast Food & Juice

The Scoop: This place was recommended by my boss’s daughter, Ann, who recently moved to Chicago. After checking out their website and learning a bit more about their story, I was sold. Here’s what they have to say: Left Coast was created from the idea that eating healthy should be quick and easy and still taste delicious […] Our philosophy is to change the perception that eating healthy is dull and flavorless.

YES. YES. YES to all of that.

What We Ate: I wanted something light and refreshing, so I ordered the Jimmy Ching salad made with napa cabbage, romaine hearts, snow peas, crunchy quinoa, cashews, green onion, mint, sesame seeds, and a Chinese mustard vinaigrette. I added some tofu to my dish for a bit of protein. It was the perfect summer salad. Bill ordered the morning buzz smoothie: espresso, cacao, peanut butter, maca powder, banana, and dates. I had a few sips, even though I don’t love the taste of coffee and really liked it. This is a great place to check out for a salad, bowl, juice or smoothie!

Ēma

The Scoop: My friend Sara, who is a fellow gluten-free foodie, enthusiastically recommended this tapas restaurant after a recent trip to Chicago. I’m so glad she did! Everything was delicious. When we arrived at the hostess stand, I saw a business card with the name “Aaron Covert, Executive Chef” on it and instantly recognized the name. We graduated from college together, and he has clearly made a name for himself, so we were that much more excited to eat there.

What We Ate: It was so hard to choose from their menu, but we were happy with everything. To simplify things for you a bit, we had the following dishes:

  • Basmati and Beluga Lentil Salad served with crispy shallots, yellow tomatoes, cucumbers, pistachios, and an orange vinaigrette. It was a light, refreshing summer salad and a great start to the meal.
  • Green Falafel with garlic tahini (I asked for a side of their garlic hummus, too – AMAZING!
  • Brussels Sprouts with crispy shallots, pumpkin seeds and sherry glaze
  • Black Lime Shrimp served with tomatoes and aleppo pepper.
  • Sea Bass special served with thinly sliced summer squash

We could have easily ordered five other dishes because everything sounded so amazing. We will definitely be back! Make sure you get a reservation, as this place gets quite busy.

The Chicago Diner

The Scoop: Because of its gluten-free options and focus on plant-based eating, The Chicago Diner was recommended by several friends. It’s in a cool artsy area of Chicago that we hadn’t been to and was within walking distance of Wrigley Field, so it was a great stop before the game. The diner is 100% vegetarian and full of vegan and gluten-free options.

What We Ate: I went with the potato tempeh hash, which consisted of crumbled tempeh, sliced potato, roasted red peppers, and onions seasoned with crushed red pepper and fennel seed. I ordered it with scrambled tofu that looked like and actually had the texture of scrambled eggs. Even Bill was surprised and approved of it, and he doesn’t even like tofu. You have to try it. It was so full of flavor and well seasoned. If we weren’t feeling so pleasantly full (but not stuffed) from brunch, we might have gone for one of their signature vegan milkshakes or their vegan and gluten-free cheesecake. Maybe next time!

Summer House Santa Monica

The Scoop: Our host at the Thompson Hotel recommended this place and we were so glad he did! What a beautiful spot. You feel like you’ve been transported to California and are hanging out in a Santa Monica summer house! It was about a mile and a half from Wrigley Field and served as our post-Cubs game meal. We had a fantastic experience and can’t say enough about how the generous and hospitable staff there treated us as we celebrated our anniversary.

What We Ate: We love guacamole but hadn’t had any yet on our trip, so we started with the guac appetizer (freebie as a result of using the Yelp! app!). We shared a few small plates including caramelized Brussels sprouts served with pancetta, whole grain mustard, and balsamic vinegar and the Emerald Kale Salad made with shredded brussels sprouts, local apples, toasted cashews, and mustard-citrus dressing. We also shared the wood-grilled fish taco platter served with black beans and rice, cilantro, salsa, and guacamole. Everything was on point, and even though we were full by the end, we each snagged a cookie from their pastry bar on our way out. They have a talented pastry chef onsite, who also happens to make gluten-free and dairy-free cookies as well, so I got the chocolate walnut cookie, which tasted just like a brownie. It was decadent and no one would possibly know it was gluten and dairy-free. 

The Little Beet Table

The Scoop: We checked out one of these on a recent trip to NYC, and after scoping out the menu, we decided to go there for our final brunch. We got there just as they were opening, so we were served quickly and had a wonderful experience. It helps that the restaurant is 100% gluten-free, which meant my options for ordering were endless!

What We Ate: We started with their banana bread served with housemade hazelnut butter. Oh my goodness. We ate the whole thing. If you can’t tell that I have a deep affinity for Brussels sprouts, you’ll know that now because we ordered them for the third time in one week – roasted Brussels sprouts served with salsa verde and sea salt. For our main entree, Bill had the avocado toast with bacon (some of the best he said he has ever had – perfectly cooked bacon), and I opted for something out of the ordinary – crispy spirulina rice. It was a round of jasmine rice served with shishito peppers, garlic, soy, ginger and topped with a farm egg. It was one of my top three favorite meals of the entire week. Perfectly seasoned, packed with flavor and fun textures, and covered with a sauce that put it over the top, this meal was a winner.

Brightwok Kitchen

The Scoop: This was our final food stop in Chicago and definitely the right choice. Brightwok Kitchen is a veggie-focused, Asian-inspired restaurant. Think of Chipotle for Asian food or sweetgreen for salads and add some on-the-spot wok preparation, and you’ve got Brightwok Kitchen.

What We Ate: It was hard to decide what to get, but I went with the Earth, Curry and Fire bowl served with chili coconut curry (I asked for mild), brown rice, tofu, kale, onions, carrots, bell peppers, and a crispy egg on top. Bill ordered the Everyday Eat Right Bowl with thai basil dressing – holy flavorville! That thing was the best. With so many options, many of which are gluten-free, you can’t go wrong!

What We Did

So, it might seem like all we do on vacation is eat, but we also love to explore new places. I’ve listed below some of the places we went to and things we did. Feel free to click each title to be linked to the website, so you can learn more.

For more recommendations in and around Chicago, visit Time Out Chicago Magazine.

  • Allyu Spa: Bill took me here for our anniversary for their couples retreat package complete with a 90-minute couple’s massage and sauna treatment. It was incredibly relaxing and one of the highlights of my week.
  • Wrigley Field: If you’re in Chicago, go see a Cubs game. It was the first time in years that I’d been in a full stadium (the Orioles are pretty terrible!), and the fans there are passionate and die hard. The chant they sing at the end when they win and the real organ that plays at each game are worth the price of admission!
  • Wendella Architectural Boat Tour: You absolutely have to go on one of these if you are in Chicago. Our tour guide was entertaining and incredibly knowledgable as he taught us about the history and architecture of the city. There are other boat tour companies that you can get deals to on Groupon.
  • Millennium Park and Cloud Gate: This is where you’ll find the famous reflective bean, tons of green space and outdoor events happening throughout the summer. 
  • The Escape Game Chicago: This was one of the coolest escape rooms we’ve ever been to. We did Gold Rush by ourselves and got out with 13 minutes to spare and teamed up with another group to escape Mission Mars. I highly recommend this place for an hour of fun!
  • The Great Escape Room Chicago: Can you tell we are a bit addicted to escape rooms? This one was one of the most unique experiences we’ve had. We did the Sherlock Library and escaped with under two minutes to spare!
  • CIBC Theater: We had to see the broadway show, Hamilton. It was amazing. The music is stuck in our heads days later. Go if you can!
  • io Improv: The improvised Shakespeare shows are phenomenal. A member of the audience gives the cast the title of a play and in 60 minutes, the actors come up with a completely improvised play. It was so fun and full of laughs.
  • Navy Pier: This is the most visited spot in Chicago and for good reason. It was one of the first places we walked to when we arrived in the city and offered a beautiful view of the city. From the new ferris wheel to the botanical garden and award-winning theater, it’s a spot you won’t want to pass by on a trip to Chicago.
  • Lincoln Park Zoo: We stopped by the zoo for about an hour or so before heading out on the boat tour, so we didn’t see much, but going to the monkey house was enough for me! I could watch the monkeys and gorillas for hours. The best part about the zoo? Admission is FREE!
  • Division Street Farmer’s Market on Saturdays from May-October. From the gluten-free crepes to the dozens of produce and flower vendors, this is worth a stop on a Saturday!

Where We Stayed

I have to admit. We did it up with hotels this trip. We usually stay in Airbnbs for the bulk of our trips and use Hotels.com or HotelTonight to book one night. I had a connection in Chicago who was kind enough to help me coordinate our stay at two of Chicago’s best hotels in the Gold Coast neighborhood. Both were in the best absolute best locations.

  • Thompson Hotel: Nicholas, who was at the front desk, gave us great recommendations for where to eat, including Summer House Santa Monica. We also had a treat in our room on our anniversary sent by a colleague, so that was a special touch!
  • The Talbott Hotel: We were warmly greeted by Perry when we arrived at The Talbott, which is run by the same group as the Thompson. Perry made us feel so welcomed and special, and he is one of the kindest people I’ve met and always had a smile on his face. We received two free drink coupons and food vouchers upon arrival and had a lovely stay for our final three nights of the trip.

I highly recommend both of these hotels! If you’re looking for regions to stay, try for east of Route 90 and North of Roosevelt Road. There’s a lot going on in North Chicago as well, like in the Lakeview area, but it’ll be a little more of a drive to the heart of downtown.

Reader Feedback

That’s a wrap, my friends! A labor of love to share with you all of the greatness and deliciousness we found on our trip to Chicago. Feel free to chime in with anything we’re missing below!