Best Hotels in Chicago: Where You Stay Shapes What You Remember

Chicago is a city that gives you options. River cruises and rooftop bars, art museums and dive bars, fine dining and deep-dish pizza served on paper plates. It’s a place of contrasts, so it makes sense that choosing where to stay can feel a little overwhelming. Your hotel isn’t just a place to sleep. It’s your base, your reset button, your view of the city.

The best hotels in Chicago don’t just offer clean rooms and good Wi-Fi. They enhance the trip. Some give you skyline views and world-class amenities. Others offer walkable access to the neighborhoods that make the city feel real. Lakeview, Wicker Park, West Loop. You can stay in a five-star high-rise or a hidden boutique with charm in every corner. It all depends on how you travel.

Budget matters. So does vibe. Are you here for a work trip or a weekend escape? Do you want to be in the middle of the action or tucked away somewhere quiet but close? Whether you care about valet parking or local coffee in the lobby, the right hotel can turn a good trip into a great one.

This guide breaks down the best hotels in Chicago based on what travelers actually look for: comfort, location, atmosphere, and value. From polished luxury to laid-back cool, there’s a place on this list that fits the way you move through a city like Chicago.

The Peninsula Chicago

Stepping into The Peninsula Chicago feels less like checking into a hotel and more like being quietly welcomed into another standard of living. Located just off the Magnificent Mile, it’s close enough to the city’s best shopping and dining to be convenient, but quiet enough to feel like a retreat. The service here is famously seamless. Staff seem to remember your name after a single interaction and the attention to detail from turndown service to how your coffee is served, borders on telepathic.

The rooms are spacious, high-tech, and incredibly well soundproofed. You can control everything from lighting to temperature to curtains from a tablet next to the bed. Bathrooms come with deep soaking tubs and TVs embedded in the mirrors. If you’re looking to unwind, the spa and indoor rooftop pool are consistently rated among the best in the city. The whole place manages to be grand without ever feeling overdone.

The Peninsula makes the case for why some hotels really are worth the splurge. It’s elegant without being cold, luxurious without being flashy. If you’re searching for the best hotels in Chicago that deliver on every promise and then some. This is a top-tier contender, especially for those who want a stay that’s just as memorable as the city itself.

📍 Location: Magnificent Mile, Near Water Tower & Michigan Ave

💰 Price Range: $$$$ (starting around $600/night)

👥 Best For: Luxury travelers, romantic getaways, high-end business stays

🌟 Notable Perks: Indoor rooftop pool, 24-hour room service, top-tier spa, Rolls-Royce house car

The Robey

The Robey is what happens when great design meets a great neighborhood. Housed in a restored Art Deco building that once served as an office tower, it blends historic architecture with cool, modern minimalism. You won’t find grand ballrooms or doormen in tuxedos here but you will find floor-to-ceiling windows, clean lines, and a rooftop that turns golden at sunset.

Located in the heart of Wicker Park, the hotel is surrounded by local coffee shops, vintage stores, record shops, and some of the best casual dining in the city. It’s ideal for travelers who don’t want to be in the thick of downtown, but still want quick access via the nearby Blue Line. You’ll see fewer selfie sticks and more locals walking their dogs, sipping cortados, or biking to a gallery opening.

The vibe is relaxed but thoughtful. Staff are casual but warm. The rooms are bright and uncluttered, with thoughtful touches like hardwood floors and vintage-style radios. If you’re looking for one of the best hotels in Chicago that feels more like a neighborhood hangout than a corporate chain, The Robey delivers charm, comfort, and a real sense of place.

📍 Location: Wicker Park (North Milwaukee Ave & Damen)

💰 Price Range: $$–$$$ (starting around $220/night)

👥 Best For: Boutique hotel fans, solo travelers, couples, creatives

🌟 Notable Perks: Rooftop bar with skyline views, Art Deco design, easy L train access

The Langham, Chicago

Walking into The Langham, Chicago feels a bit like stepping into a museum, if museums smelled like fresh orchids and had beds you never want to leave. Designed by Mies van der Rohe, the building is a modernist masterpiece, and the interiors follow suit: warm tones, clean lines, and a quiet kind of elegance that never tries too hard.

The riverfront location is one of the best in the city. You’re a short walk from Millennium Park, Michigan Avenue, and the Loop, but the hotel itself is so peaceful you almost forget you’re in the middle of it all. Rooms are large, and almost every one has stunning views of the Chicago River. The Chuan Spa is a destination in itself, regularly voted among the best in the U.S., and the afternoon tea in the Pavilion Lounge is a nod to the brand’s British roots.

Where The Langham really excels is in its consistency. Every interaction. From front desk to housekeeping feels polished and sincere. If you’re looking for the best hotels in Chicago that blend impeccable service with sleek, contemporary comfort, The Langham is hard to beat.

📍 Location: River North, right on the Chicago River

💰 Price Range: $$$$ (starting around $550/night)

👥 Best For: Design lovers, spa enthusiasts, business travelers

🌟 Notable Perks: Award-winning spa, floor-to-ceiling river views, exceptional service

LondonHouse Chicago

LondonHouse Chicago blends old-world elegance with new-world energy. The hotel is housed in a beautifully restored Beaux-Arts building, where the classic façade hides sleek interiors and floor-to-ceiling views of the Chicago River and Lake Michigan. Step into the lobby and you’re greeted with bold design, moody lighting, and a sense that you’ve just entered somewhere distinctly urban but unmistakably Chicago.

Its biggest claim to fame is the rooftop. Arguably the best in the city. Whether you’re sipping a cocktail at sunset or just taking in the skyline with a camera in hand, the 22nd floor terrace delivers a view that belongs on postcards. Rooms are modern and comfortable, with plush beds and smart layouts that make even the standard categories feel elevated.

If you're looking for the best hotels in Chicago that give you unbeatable access to landmarks, restaurants, and those once-in-a-trip views, LondonHouse checks all the boxes. It’s stylish without being too serious, and luxurious without pushing into intimidating territory. Just right for a city break you’ll actually remember.

📍 Location: Downtown Chicago, at the corner of Michigan Ave & Wacker Dr

💰 Price Range: $$$ (starting around $300/night)

👥 Best For: Couples, first-time visitors, skyline lovers

🌟 Notable Perks: Panoramic rooftop bar, historic architecture, spa with river views

Hotel Lincoln

Hotel Lincoln doesn’t try to be flashy and that’s exactly why it works. Located across from Lincoln Park and the free zoo, this hotel leans into its quirky, laid-back character. From vintage-inspired furniture to colorful art by local creators, everything about the space feels handcrafted and lived-in. It’s the kind of place where you can walk in wearing jeans and still feel like you belong.

The rooftop bar, J. Parker, offers sweeping views of Lake Michigan and downtown without the velvet rope energy. Downstairs, the neighborhood itself is the real draw. You’re steps away from quiet running trails, family-friendly spots, and great brunch options that locals actually go to. The Red Line is nearby if you want to head downtown, but chances are you’ll enjoy staying in the area just as much.

For travelers who care more about vibe than valet service, Hotel Lincoln is one of the best hotels in Chicago to get a feel for the city beyond the postcard highlights. It’s casual, creative, and full of character. Exactly what a neighborhood stay should be.

📍 Location: Lincoln Park, across from the park and zoo

💰 Price Range: $$–$$$ (starting around $180/night)

👥 Best For: Casual travelers, families, local explorers

🌟 Notable Perks: Rooftop bar, neighborhood charm, walkable to lakefront

The Hoxton, Chicago

The Hoxton, Chicago is more than just a place to sleep. It’s where locals and travelers blur together over cocktails, art, and playlists that make you Shazam every five minutes. Located in West Loop’s buzzing Fulton Market District, this hotel brings together mid-century aesthetics, open workspaces, and a social vibe that feels alive from morning coffee to late-night bites.

The rooms aren’t huge, but they’re thoughtfully designed: smart lighting, rich textures, and floor-to-ceiling windows that frame the neighborhood’s industrial charm. Downstairs, the lobby doubles as a co-working and social space, often filled with a mix of laptops, espresso cups, and informal meetings. Upstairs, the rooftop pool and cabana area offer a refreshing break during Chicago’s summer months and a rare outdoor bonus in the city hotel scene.

For guests who travel light but live loud, The Hoxton is one of the best hotels in Chicago to soak up the city’s creative energy. It’s where style meets substance, with enough personality to make you feel like you found a city within the city.

📍 Location: West Loop, steps from Fulton Market

💰 Price Range: $$$ (starting around $260/night)

👥 Best For: Creative professionals, city explorers, foodies

🌟 Notable Perks: Stylish rooms, rooftop pool, buzzing lobby scene

The Gwen, a Luxury Collection Hotel

The Gwen is a hotel that knows how to make an entrance. Tucked inside a landmark 1920s building with ornate Art Deco detailing, it blends classic glamour with modern hospitality. From the sculptural lobby to the curated artwork throughout, every corner feels intentional. And the best part? You're literally connected to one of Chicago’s best shopping centers, making retail therapy easier than ever.

The rooms are generously sized, with plush beds, high ceilings, and windows that showcase either the glittering skyline or the vibrant Michigan Avenue bustle. The rooftop terrace is a quiet highlight, perfect for evening cocktails or just watching the lights bounce off the city’s iconic architecture. Service is polished but not stiff. Exactly what you’d expect from a Luxury Collection property.

If you’re looking for one of the best hotels in Chicago that lets you live out a classic city fantasy. Shopping bags in hand, cocktails at dusk, and elegant comfort after a long day. The Gwen offers that dream with a gold-trimmed ribbon.

📍 Location: Magnificent Mile, adjacent to the Shops at North Bridge

💰 Price Range: $$$$ (starting around $400/night)

👥 Best For: Luxury seekers, design lovers, couples on a city escape

🌟 Notable Perks: Art Deco elegance, rooftop terrace, direct mall access

Viceroy Chicago

Viceroy Chicago makes a strong first impression. From its sleek glass tower to the golden accents inside, it’s clear this isn’t your standard city hotel. The design is bold but warm, mixing mid-century glamour with sharp, modern touches. Located in the Gold Coast, it gives you easy access to the lakefront, high-end boutiques, and some of the city’s most beautiful residential streets.

The rooms are polished and plush, with floor-to-ceiling windows that make the most of the city views. The rooftop pool is a summer magnet, and the on-site restaurant, Somerset, is a favorite not just for guests but for locals who appreciate well-executed New American cuisine. From the artwork to the scent in the lobby, everything here feels curated.

For travelers who want one of the best hotels in Chicago that balances style, location, and livability, Viceroy hits that sweet spot. It’s youthful without being loud, luxurious without being cold, and effortlessly cool without even trying.

📍 Location: Gold Coast, near Oak Street Beach & upscale shopping

💰 Price Range: $$$ (starting around $280/night)

👥 Best For: Design-conscious travelers, couples, modern luxury fans

🌟 Notable Perks: Rooftop pool, bold interiors, top-rated on-site restaurant

The Publishing House Bed and Breakfast

The Publishing House feels more like staying at a friend’s elegant city loft than a traditional hotel. Housed in a beautifully restored building that once held a printing press, it now offers a warm, artistic space with just 11 individually designed rooms. Each named after a famous author. It’s small, it’s soulful, and it doesn’t try to be anything other than deeply personal.

Mornings begin with a breakfast that’s closer to a brunch you'd pay $30 for elsewhere, made from scratch in an open kitchen. The communal living space encourages conversation, reading, or just sipping coffee by the fireplace. And when you’re ready to explore, you’re steps away from Chicago’s best restaurants, markets, and galleries in the ever-evolving West Loop.

If you’re the kind of traveler who values atmosphere over amenities and conversation over concierge apps, this might be one of the best hotels in Chicago for you. It’s cozy, thoughtful, and filled with the kind of charm that lingers longer than checkout time.

📍 Location: West Loop, near Randolph Street & Fulton Market

💰 Price Range: $$–$$$ (starting around $250/night, includes breakfast)

👥 Best For: Couples, solo travelers, boutique hotel lovers

🌟 Notable Perks: Gourmet homemade breakfast, literary-themed rooms, intimate setting

Freehand Chicago

Freehand Chicago is the perfect mix of affordability and personality. It’s housed in a historic building but redesigned with vibrant decor, local artwork, and a social energy that’s hard to find in bigger hotels. With both private rooms and shared bunk-style dorms, it’s an ideal choice for backpackers, solo travelers, or anyone who prefers spending more on experiences than on where they sleep.

What makes Freehand stand out is its community feel. The on-site cocktail bar, Broken Shaker, has won awards and regularly draws a local crowd, so you’re just as likely to meet Chicagoans as fellow travelers. The shared spaces like the lobby lounge and communal kitchen are full of people working, chatting, or planning their next move.

For travelers who value creativity, conversation, and cost savings, Freehand is one of the best hotels in Chicago in its price range. It’s proof that budget doesn’t have to mean boring.

📍 Location: River North, close to public transit and nightlife

💰 Price Range: $–$$ (starting around $100/night for shared, $170+ for private)

👥 Best For: Budget travelers, solo explorers, digital nomads

🌟 Notable Perks: Hostel-style shared rooms, lively cocktail bar, creative common areas

Waldorf Astoria Chicago

Waldorf Astoria Chicago is elegance with the volume turned down. Tucked into the refined Gold Coast neighborhood, it trades the buzz of downtown for leafy streets, quiet cafes, and a sense of calm that’s rare in a city hotel. From the moment you enter the grand courtyard, you feel like you’ve stepped into a different rhythm. Slower, softer, and deeply luxurious.

Rooms here are some of the largest in the city, many with private terraces, deep soaking tubs, and even working fireplaces. It’s one of the few places where you can genuinely escape within the city. The spa and wellness offerings are also standout features, with a 14,000-square-foot facility that includes a lap pool, eucalyptus steam rooms, and a full-service salon.

For travelers seeking the best hotels in Chicago not just for luxury, but for tranquility, the Waldorf offers a level of privacy and refinement that’s hard to top. It’s less about being seen, and more about feeling completely cared for.

📍 Location: Gold Coast, near Oak Street and the lakefront

💰 Price Range: $$$$ (starting around $600/night)

👥 Best For: Luxury travelers, couples on a romantic trip, wellness seekers

🌟 Notable Perks: In-room fireplaces, private terraces, upscale spa & lap pool

Picking the Right Place to Stay in a City That Never Sits Still

The best hotel in Chicago isn’t about finding the one perfect hotel. It’s about knowing what kind of trip you want to have. This city has as many personalities as it does neighborhoods. Whether you're drawn to the architectural heart of downtown or the artsy calm of a local district, where you stay shapes how you experience Chicago.

If you're splurging and want to be wrapped in luxury from check-in to checkout, a place like The Peninsula or Waldorf Astoria will more than deliver. But if you’d rather save that money for food tours and museums, options like Freehand or Hotel Lincoln offer comfort, style, and prime location without the premium price tag.

Some hotels in this guide are made for those who never stop moving. Others are built for slowing down and soaking in the skyline. The good news? In a city like this, the right place isn’t hard to find. It just depends on whether you want to see Chicago like a guest or live in it like a local, even if it’s just for a weekend.