Check Into the Rainbow: 3 Chicago Hotels That Make Us Feel At Home

Chicago is a mosaic of distinct neighborhoods, rich architectural history, and a legendary queer culture that beats at the heart of the Midwest. Whether you are looking to dance the night away in the country’s first officially recognized gay village, sip cocktails with panoramic lake views, or step out right onto the city’s glittering downtown pulse, your choice of home base sets the tone.

 

Here is an insider’s guide to three standout stays that anchor you in Chicago’s most vibrant, stylish, and welcoming neighborhoods. NOTE: We were there in early October so you’ll see some Halloween decorations in many of the pictures. 

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1. Wrigleyville & Lakeview: Hotel Zachary

If your ideal getaway blends historic character with immediate access to Chicago’s iconic LGBTQ+ epicenter, Hotel Zachary is a home run. Located directly across from Wrigley Field, this design-forward boutique property is steeped in neighborhood warmth and sits just a short 8-minute scenic stroll or very quick rideshare away from Northalsted (historically known as Boystown), America’s first officially recognized gay village.

• The Vibe: Sophisticated vintage meets neighborhood living room. Named after Zachary Taylor Davis, the visionary architect behind Wrigley Field, the hotel channels a timeless, mid-century residential aesthetic.

• The Neighborhood Scene: You are minutes from the pulsing heart of Chicago’s queer nightlife. Spend your evening exploring Northalsted’s legendary drag bars, dance clubs, and welcoming pubs, then retreat to the North Side. Closer to the hotel, grab handcrafted cocktails and Mediterranean-infused bites at the hotel’s own Alma, or wander the independent cafes and vinyl shops lining Lakeview.

Our stay at Hotel Zachary was actually the fifth night of our Chicago trip and we only stayed there one night. We took our little 8-minute walk to the gayborhood and enjoy a great night at Sidetracks and Roscoe’s and finish the evening off with the pizza slice or two from Big Gay Sal’s Pizza. We were surprised the pizza joint had a bouncer, but they sold alcohol, too.

I will say it’s been about 16 years since I’ve been to Chicago. Roscoes was still great, a different set up than when I was there last, but still pretty functional. And Sidetracks is still a great spot, but I think their dj wanted to clear out the crowd as he started playing a lot of K-pop which did not match the clientele that evening, so that’s why we left and got pizza.

2. Lincoln Park & Old Town: Hotel Lincoln

Tucked right where urban energy meets leafy tranquility, Hotel Lincoln (a JDV by Hyatt hotel) places you in one of Chicago’s most picturesque, art-forward districts.

• The Vibe: Indie-chic, artistic, and effortlessly cool. It’s a favorite for creatives, design lovers, and travelers who want a boutique feel with killer views.
• The Neighborhood Scene: Wake up and cross the street to explore the multi-mile green expanse of Lincoln Park, the historic Lincoln Park Conservatory, and the beloved Lincoln Park Zoo. Walk down the gorgeous, boutique-lined blocks of Armitage Avenue for local shopping, or head up to the hotel’s crown jewel: The J. Parker, a stunning rooftop lounge serving up inventive cocktails against a backdrop of Lake Michigan and the downtown skyline. Plus, you’re just a quick transit hop away from both the North Side gay scene and downtown.

We bounced over to the hotel Lincoln because of its great location and we knew they were going to be great views of the lake as well as the famous Lincoln Park. Out of the three hotels, we think the attention to our stay, the greeting, making sure we were settled in and knew of some of the options in the area, we felt really at home with the staff. They made sure we knew there was a farmers market across the way the next day and of course, remind us of the free Lincoln Park Zoo.

Of course, they mentioned the J. Parker Rooftop Bar which we had on our list to dine at already and we’re so glad we did. Dinner there was a simple evening enjoying a new space and a great time people watching. And the people were of all different demographics, which I loved. To have a great hotel right next to a great natural resource and zoo, we are very happy. We chose to stay at Hotel Lincoln for two nights. We were there for two nights so we also had some nice bites at the attached but not associated restaurant Americano. Next time, maybe we will check out Sushi Suite 202.

We were also close to the Koval Distillery. We had a great tour and tasting, and had drinks before and after, and almost joined a festive birthday party of 20 gay men. So we did pick a good gay friendly place to enjoy. 

And this is a hotel we originally came to for this Chicago trip. We had a conference that was being held there and decided to double in the other two areas of Chicago to get a good feel of the city. But this was a great spot as it is right near Magnificent Mile, a lot of shopping, Chicago River experiences, Millennium Park, and great transportation to other spots in the city.

We were able to check of a massive bucket list item this trip – a tour of the Chicago River. Thanks to the Chicago Architecture Center, we had am epic time seeing a side of Chicago we never knew. Ten thumbs up!

For 90 captivating minutes, guests travel all three branches of the Chicago River, surrounded by open-air, 360-degree views and the stories behind more than 50 iconic buildings. Along the way, passengers glide beneath 13 historic bascule bridges and learn about the visionary architects and engineers who shaped Chicago’s skyline. From art deco and neoclassical landmarks to mid- century modern and postmodern towers, the tour reveals how bold ideas helped shape one of the world’s most influential architectural cities.

Since we were downtown, we were also close to Union Station, and an inexpensive and quick train ride west to Brookfield Zoo, Chicago. We will need to go again and plan better timewise for when we walked around, we saw people feeding the kangaroos and the giraffes. we want to do that!  We actually did get to do the giraffes as that was a walk-up station, but the others, plan ahead, just in case.

There are Wild Connections: Feeding the Animals (penguins, giraffes, flamingoes), and Wild Connections: Animal Encounters (penguins, kangaroos, jellyfish), so check out Brookfield Zoo Attractions to plan your close and personal times with the animals. We may pop back next month to see Chicagoland’s Longest-Running Holiday Lights Festival at the Brookfield Zoo. 

We’ve been lighting up the night for 45 years! Explore 3.5 million lights, themed areas, light tunnels and a glowing maze. Meet Santa, warm up with the animals, and make new memories just west of downtown Chicago.