Boutique Hotels in Chicago → 24 Unique Places with Pools and Rooftops!

Boutique Hotels in Chicago

Traveling to the big old Windy City? Well, you’re in for a treat, because this place is truly special, just like its boutique accommodations! There are many places to stay in Chicago but I’ve looked for hours and found the top ones.

Scroll below, and find the best boutique hotels in Chicago, which I hand-picked myself, and only included the ones with amazing reviews. I also added them from most to least expensive so you can easily pick them.

Since the city is packed with unique hotels, I’ve thought I’d make 2 more bonus sections for anyone who’s looking for something a bit more specific. The first one has the top hotels for couples and the second one has a list of the best accommodations with a pool.

NOTE: If you’re planning to visit Chicago during the summer then you should know that hotel prices are higher during that time (June, July and August) by US$100 to US$200. So I would recommend booking way up in advance if your holiday is then.

Yep, we’ve got lots to see today so buckle up and let’s start!

Quick Picks for Your Stay

If you’re looking for a short summary of the post. Check out the list below! It has the best boutique hotels in Chicago:

I’m lost without some sort of digital map! If you also need something visual to guide you, then check out the map below, which will be super helpful!

Luxury (US$250 and up)

1 1 Hotel Zachary best luxury hotels in Chicago
  • Hotel Zachary – There’s nothing like booking a unique boutique hotel for your trip! Especially in Chicago’s Lakeview area. Beautifully decorated with elegant furniture and soft color palettes the hotel has spacious rooms with floor-to-ceiling windows (some even come with hardwood floors). With 2 restaurants on-site, room service and a fitness center this place is surely a keeper!
  • Nobu Hotel Chicago – Loving this boutique property that has such modern amenities and looks! Once here, you’ll feel as if you’re in one of those Pinterest minimalistic houses! The hotel offers simple yet chic guest rooms, an indoor pool and a restaurant. But the crown jewel is definitely their rooftop bar which has the most amazing city views (especially at night)!
  • Hotel Blake – If you’re a lover of old buildings then you’ll love this historic boutique hotel that’s set near Grant Park and Millennium Park. The accommodation offers private rooms that have a private bathroom with a rainfall showerhead, and a restaurant where you can enjoy a yummy breakfast in the morning! Don’t forget to book your boutique hotels in Chicago ASAP, these ones will sell out super fast!
1 2 hotels with free parking Chicago USA
  • Soho House – Beautifully combining the old with the new, this Chicago hotel (which is set in a former belt company) offers rooms with custom-made furniture that will have you ask them for their designer’s number, rainforest showers and a dining area. A local hub for musicians and artists, the Soho House knows how to entertain its guests with their fun music shows and incredible rooftop lounge.
  • Sophy Hyde Park – A boutique hotel where art lovers will feel in their element! This sophisticated accommodation will make you feel like you’re staying in an Art Institute! Everything is so well-picked especially in the rooms which have plush lounge seating and a marble-tiled bathroom.
  • Chicago Athletic Association – Set in a landmark building that boasts a grand ballroom with 19th century stained glass windows, this boutique hotel in Chicago offers rooms with such unique furniture! You’ll never want to leave! Nor will the kids when they see the game room on site!

Mid Range (from US$150 – US$250)

2 1 boutique Chicago hotel for romantic honeymoon
  • Hotel EMC2 – Want to be close to all the dining and shopping on the famous Magnificent Mile street? Then book a room at this boutique hotel that stands out with its one of-a-kind designs! Every room features such cool features like paintings, and large windows that overlook the city lights! But make sure you don’t just stay in your room because I hear the crafted cocktails at their tavern are unmissable!
  • Silversmith Hotel – Set in a historic building that was originally built in the 1800s in Downtown Chicago, near Millenium Park and not too far from Wicker Park, this hotel has a contemporary design yet the elegant elements so specific to most hotels in the city aren’t missing. All the rooms here also come with a coffee maker and free wi-fi.
  • Thompson Chicago – Class, elegance and fabulous views of the Chicago skyline! This boutique hotel set in the Gold Coast, Chicago’s historic district, sure knows how to make one feel at home! Featuring rooms with floor-to-ceiling windows and a fabulous restaurant where you can indulge in handmade pasta and their signature cocktails, this fancy hotel is one of the best places to stay in the city!
2 2 The Publishing House Bed and Breakfast
  • Ivy Boutique Hotel – I like hotels that know how to make a simple decor look special! Located near the Magnificent Mile, Ivy Boutique Hotel is so perfect for a Chicago getaway. Wake up each morning to the most amazing views from the floor-to-ceiling windows, and head out to the rooftop lounge terrace for the first coffee of the day and some breakfast!
  • The Guesthouse Hotel – Designed to make guests feel right at home this super cozy hotel is set a bit further away from Downtown Chicago but closer to the beach (yay)! Each suite here is equipped with a small kitchen, a balcony (and some even have a fireplace). After a day of exploring Lincoln Park and the other attractions in the city, make sure you drop by the spa on-site to relax and prepare for a new day in the city!

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Budget (up to US$150)

3 1 Where to stay for cheap in boutique Chicago hotel
  • The Publishing House Bed and Breakfast – I love how diversified this place is! It kind of resembles an office building turned into a place where everyone can crash! You can definitely feel the chill atmosphere and of course the furniture and all the other elements contribute to that as well. The accommodation offers a free breakfast in the morning and some suites with a dining area and a flat-screen tv.
  • The Talbott Hotel – Preparing for a fun trip in Chicago? Then you’ll need a fabulous hotel that’s right in the middle of the action! This awesome place is just steps away from all the bars and restaurants on the Magnificent Mile and from Oak Street Beach. The hotel has such lovely rooms decorated with good-taste (simple yet chic, just how I like it). And of course it has a bar where you can enjoy your nightcap and mingle with some friendly guests!
  • Acme Hotel Company Chicago – Quirky paintings and wallpapers, amazing rooms with the latest visual and audio technology and an awesome location near the Magnificent Mile and not too far from the Wicker Park area! What more could you wish for? This amazing hotel has it all plus a fabulous lounge bar where you can try the craziest cocktails that will get you started for the evening!
3 2 Unique places to stay in Chicago
  • Staypineapple, An Iconic Hotel – Who’s a big pineapple fan? Well, if you are then I think this hotel is for you! Decorated with pineapple motifs, mosaic floors and marble ceilings, the boutique hotel is set only a short walk away from Michigan Avenue and Millennium Park. The rooms have mahogany furnishings and modern amenities (some even offer views of Millennium Park and Lake Michigan).
  • Hotel Lincoln – Located not too far from the North Side area and right near the beach this awesome hotel has such amazing rooms decorated with art pieces by local artists. Plus they also offer bike rentals during the summer so you can explore the town! Wow, and I’m not done! La pièce de résistance is surely their rooftop bar, where you can enjoy a few cocktails at the end of the day after a long day of visiting attractions!
👑 Luxury price:$200
🏨 Mid Range:$180
🛏️ Budget:$120
🛎️ Best luxury hotel:Hotel Zachary
🧳 Best mid-range hotel:Hotel EMC2 
👛 Best budget hotel:The Publishing House Bed and Breakfast
💌 Top hotel for couples:The Peninsula

BONUS 1: Cool hotels for couples

Cool hotels for couples

Planning a romantic getaway to Chicago? Then you’ll need some amazing hotels to stay in with your partner! Although the list above is pretty amazing, I’ve decided to add some special places that will offer you all the privacy and facilities you need, so let’s have a look.

All the hotels below are luxury and mid-range with prices from US$200 to US$450:

  • The Peninsula – Start your day with a spa sesh at this amazing hotel that’s located near the Museum of Contemporary Art. Once you’re both feeling more relaxed you can head for a swim in the indoor pool which overlooks the city and then get ready to hit the town (by the way, your room will have a soaking tub)! End your day with a romantic dinner at the award-winning restaurant on-site.
  • Virgin Hotels – What better way to celebrate your holiday then with some drinks on the rooftop bar with your significant other at sunset? This amazing hotel also offers 5 restaurants and a nightclub! Combining both leisure and fun, the accommodation has a nice leisure room with a fireplace where you guys can relax and read some books borrowed from the library!
  • Kimpton Hotel Monaco – Class, elegance and such amazing services! Leave it to Kimpton Hotel to offer all tourists an unforgettable experience in Chicago! Relax with your partner your fabulous rooms which have spa facilities and yoga mats (in case you need a good stretch after your flight)! The eco-friendly hotel offers a daily evening reception in the lobby and a restaurant.
  • Sofitel Chicago Magnificent Mile – The French art de vivre furnishings and décor, will definitely spark the romance and make you feel like you’ve traveled to Paris, the city of love! Set in a prism glass building, this hotel offers the most amazing view over Chicago. Once you get settled in, head to their restaurant to enjoy a French-inspired dinner and some wine!

BONUS 2: Top boutique hotels with a pool

Top boutique hotels with a pool in Chicago

Looking for some fabulous hotels in Chicago that have a pool? Then you’re in the right place! There’s nothing like a nice long swim to start your day or to end it before you head to bed. Luckily I’ve found some amazing places in the city that offer this possibility and I’ve compiled the best ones in the list below.

All the accommodations are mid-range and luxury with prices from US$200 to US$400:

  • The Langham – Rooms with large windows, incredible views and a pool that’s waiting to be used! Oh how I love holiday time! This amazing hotel near the United Center and Wicker Park area, is set in a skyscraper designed by renowned architect Mies van der Rohe. The accommodation offers an award-winning wellness retreat and rooms with a deep soaking bathtub.
  • Viceroy Chicago – Save the best at the end! This historic hotel has the most fabulous rooftop pool! Set near the Gold Coast, the accommodation comes with rooms that have floor-to ceiling windows and a restaurant. Start your morning with some coffee and breakfast and then head to the rooftop pool for a quick dip to start your day right!
  • The Hotel & Athletic Club – Looking to combine a holiday filled with activities with some relaxation as well? Then book a room at this hotel which offers spa services, an outdoor pool and a yoga studio. There’s nothing like relaxing in the steam room after a long stretch in the yoga class!
  • The Robey – Set in the heart of Chicago’s Wicker Park neighborhood, this accommodation offers a seasonal outdoor swimming pool, and simple but beautifully decorated rooms. Enjoy your day exploring Wicker Park and then come back to the hotel to catch the sunset on the rooftop lounge of the hotel.

FAQs about Boutique hotels in Chicago

chicago usa

💸 What is the average cost of a hotel room in Chicago?

The average cost of a hotel room in Chicago is around US$180 in general, and in the summer US$300 as hotels are much more expensive during that time.

🤩 Which is the best boutique hotel in Downtown Chicago?

Hotel EMC2 is one of the best boutique hotels in Chicago Downtown! The accommodation is near all the major attractions and it has so many cool facilities.

📸 Where do celebrities stay in Chicago?

Celebrities usually stay at The Peninsula hotel. Famous people like Jennifer Aniston and Aaron Eckhart were seen here.

🏊 Which are the best boutique hotels in Chicago with a pool?

The Langham and Viceroy Chicago are some of the best boutique hotels in Chicago with a pool. Both accommodations have great reviews and amazing amenities.


chicago sculpture

Wow! How amazing are these boutique hotels in Chicago? I’m sure now you feel much more excited for the trip!

Before we wrap up and everyone goes back to planning their trip I think we should do a short recap of what we’ve talked about today.

The post has the best boutique hotels in Chicago, listed from most to least expensive, plus 2 bonus sections, the first one with some amazing accommodations for couples and the second one with unique hotels with a pool.

Decisions, decisions! I know it’s hard to make one when you’ve got so many possibilities. But don’t worry, I’m here to help you as much as I can. So if you’re not sure which one to pick, check out my 2 favorite boutique hotels in Chicago:

  • Hotel Zachary – Set in the beautiful Lake View area this amazing hotel has amazing decor which include hardwood floors and floor-to-ceiling windows
  • Hotel EMC2 – A fabulous hotel in Downtown Chicago that offers a great atmosphere, rooms with unique paintings, and yummy cocktails

This city may be big, but it’s also packed with tourists. I recommend booking your boutique hotels in Chicago super early (especially in the summer when the prices are higher). Otherwise, you may end up paying way too much or not finding the room you want!

What an adventure! I hope you have as much fun visiting this city as I had writing this post on the best boutique hotels in Chicago!

I’ll leave you to your business now but don’t forget I’m always here if you need some guidance. Just pop a comment below and I’ll make sure to answer as soon as I can!

Safe travels,


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