Chicago is a city that does it all—skyline views, lakefront breezes, Michelin-starred dining, and soulful neighborhoods that invite exploration. Whether you’re visiting for a romantic weekend, a cultural escape, or a city adventure with your favorite person, where you stay can make all the difference. These places to stay in Chicago have their own vibe, personality, and way of capturing the city’s spirit.
Best Places to Stay in Chicago, Illinois
For Sports Fans: Hotel Zachary
Hotel Zachary felt like the heartbeat of Wrigleyville—baseball nostalgia with polished charm and a front-row seat to all the action. I remember sipping coffee on the balcony, Wrigley Field just across the street, thinking, "This city doesn’t just show up—it shows off."
What I Loved Most: The blend of vintage Cubs history and fresh, modern style—it felt timeless without trying too hard.
My highlight? A crispy pork belly sandwich and frosé at Big Star downstairs, followed by an evening stroll through Clark Street.
Plan your trip:
- Vibe: Sporty-chic, vibrant, neighborhoody
- Highlights: Balcony rooms, Wrigley Field views, walkable dining, bar on site
- Best For: Baseball fans, weekenders, local explorers
- Address: Hotel Zachary, 3630 N Clark St, Chicago, IL
Chicago Hotel For Budget-Conscious Travelers: FOUND Chicago River North
FOUND Chicago River North felt like a secret clubhouse—industrial finishes, vintage flair, and that unshakable feeling of being somewhere creative. I remember lounging in the lobby with a record spinning nearby, thinking, "This is the cool kid’s version of home."
What I Loved Most: The affordability without sacrificing style—every detail felt intentional.
My highlight? Ramen and a negroni at the on-site speakeasy-style bar Steingold's of Chicago—cozy, moody, and delicious.
Plan your trip:
- Vibe: Urban, affordable, creative
- Highlights: Shared or private rooms, café, bar, central River North location
- Best For: Budget-conscious couples, solo travelers, indie spirits
- Address: FOUND Chicago River North, 613 N Wells St, Chicago, IL
For Young Creatives: Acme Hotel Company
Acme Hotel Company felt like a rock concert wrapped in boutique luxury—bold colors, smart tech, and cheeky energy at every turn. I remember blasting Spotify through the in-room speakers while getting ready, thinking, "This is where the night starts."
What I Loved Most: The personality—every hallway, mirror, and mug had something clever to say.
My highlight? Morning espresso from the lobby’s West Town Bakery, paired with a vanilla-glazed cruller and a smile from the barista.
Plan your trip:
- Vibe: Edgy, upbeat, modern
- Highlights: High-tech rooms, on-site bakery, walkable to Mag Mile, social energy
- Best For: Young couples, music lovers, playful stays
- Address: Acme Hotel Company, 15 E Ohio St, Chicago, IL
Chicago Hotel For Artsy Urbanites: Freehand Hotel
Freehand Hotel felt like a downtown artist’s loft—warm woods, shared stories, and soft jazz rolling out of the lobby bar. I remember sipping a mezcal cocktail at the counter, thinking, "This is the kind of place that doesn’t need to shout to be cool."
What I Loved Most: The social energy—friendly faces, bohemian spirit, and that feeling that everyone has a story to tell.
My highlight? Dinner at The Broken Shaker: cauliflower shawarma, citrusy cocktails, and fairy lights strung across the ceiling beams.
Plan your trip:
- Vibe: Warm, artsy, social
- Highlights: Cocktail bar, cozy design, shared or private rooms, near the Red Line
- Best For: Creative couples, travelers who love community, casual adventurers
- Address: Freehand Hotel, 19 E Ohio St, Chicago, IL
For Tech-Lovers: Hotel EMC2
Hotel EMC2 felt like sleeping inside a science experiment—sleek, whimsical, and filled with playful curiosity. I remember the moment the robot butler delivered extra towels, thinking, "This is the future—and it’s fabulous."
What I Loved Most: The fusion of art and science—Edison bulbs, glass showers, and a sense of delight in every detail.
My highlight? Dinner at The Albert: black truffle tagliatelle with mushroom foam and a side of live jazz from the corner booth.
Plan your trip:
- Vibe: Tech-forward, artsy, futuristic-chic
- Highlights: Robotic butler, in-room Alexa, fine dining, inspiring design
- Best For: Curious minds, design lovers, creative couples
- Address: Hotel EMC2, 228 E Ontario St, Chicago, IL
For Stylish Couples: Viceroy Chicago
Viceroy Chicago felt like a modern masterpiece—marble accents, rooftop reflections, and skyline views that made everything feel cinematic. I remember stepping onto the rooftop at dusk, thinking, "This is where city dreams go to glow."
What I Loved Most: The pool overlooking the skyline—swimming with skyscrapers all around was surreal.
My highlight? Brunch at Somerset: lemon ricotta pancakes, grapefruit mimosas, and sunshine streaming through tall windows.
Plan your trip:
- Vibe: Sophisticated, glamorous, elevated
- Highlights: Rooftop pool, upscale dining, Gold Coast location, luxury design
- Best For: Special occasions, stylish couples, luxury weekenders
- Address: Viceroy Chicago, 1118 N State St, Chicago, IL
Kinzie Hotel
Kinzie Hotel felt like a true urban basecamp—cozy rooms, buzzing neighborhood, and everything within a short walk. I remember looking out over River North with a nightcap in hand, thinking, "This city has rhythm—and we’re in the middle of it."
What I Loved Most: The balance—affordable without compromise, warm without pretense.
My highlight? Complimentary evening drinks and snacks in the lounge, followed by a deep-dish nightcap at Lou Malnati’s next door.
Plan your trip:
- Vibe: Central, inviting, unpretentious
- Highlights: Free evening reception, breakfast delivery, walkable location
- Best For: Couples who love exploring, practical travelers, first-time visitors
- Address: Kinzie Hotel, 20 W Kinzie St, Chicago, IL
Conclusion
From rooftop cocktails to cozy rooms in the heart of the city, these Chicago hotels offer something special for every kind of traveler. Whether you're planning a romantic retreat, a girls’ getaway, or a solo city break, there's a stay here that feels just right.
Looking to explore more of the state? Don’t miss these romantic getaways in Illinois and discover the top resorts across the state. Want some summer inspiration? Check out the best Illinois beaches or plan one of the ultimate girls’ weekend getaways in the U.S..
No matter how you experience it, Chicago makes it easy to fall in love—with the city, and maybe with each other all over again.