Iconic attractions, fabulous dining and incredible architecture is the best way to describe Downtown Chicago. If you are looking to take a city break filled with glamorous shopping, exploring around famous landmarks and relaxing around a rooftop pool whilst soaking up the sun, then this is the destination you are going to want to check out. With so many great accommodations to choose from, this article is going to take you through the 20 best Downtown Chicago hotels with rooftop pools so that you can find the perfect one to book for your stay.
20 BEST DOWNTOWN CHICAGO HOTELS WITH ROOFTOP POOLS
Within this article I have compiled a list of the 20 best Downtown Chicago hotels with rooftop pools to help make it easier for you to find the ideal accommodation for your trip to this vibrant city. These hotels have been hand picked by me because of their fabulous locations, breathtaking rooftop pools and on-site amenities.
My two personal favourite Downtown Chicago hotels with rooftop pools are The Hoxton, Chicago for its hip roof top pool and trendy interior décor, alongside The Robey, Chicago, a Member of Design Hotels with its impressive bar area and spacious rooftop pool.
QUICK PICKS: 3 BEST DOWNTOWN CHICAGO HOTELS WITH ROOFTOP POOLS
If you haven’t got the time right now to read through this entire article, don’t worry I have your back. Below I have noted the 3 best Downtown Chicago hotels with rooftop pools to make booking your accommodation even easier. However, I would suggest saving this article for later as the hotels listed throughout are incredible and not to be missed.
DoubleTree by Hilton Chicago Magnificent Mile
- Chic rooftop pool
- Nearby popular attractions
- On-site restaurant
ACCOMODATION COMPARISON TABLE
Throughout this article you will discover the best Downtown Chicago hotels with rooftop pools. The table below showcases the current cost per night for two adults which may change. You can choose from breathtaking views, in-house spa facilities with fabulous rejuvenating treatments and sunset dining opportunities. With so many options you are ensured to find the most ideal hotel to suit you travel plans in Downtown Chicago.
20 BEST DOWNTOWN CHICAGO HOTELS WITH ROOFTOP POOLS
When it comes to finding a fabulous hotel in Downtown Chicago it isn’t difficult. The options you have to choose from are endless which is why I have accumulated this list of the 20 best Downtown Chicago hotels with rooftop pools to take away some of the stress you can endure when booking a trip. The perks of booking one of Downtown Chicago hotels with rooftop pools is that it adds that extra bit of vacay feel that you will most definitely want to indulge in.
The Hoxton, Chicago
This is the hotel that you are going to call your home away from home. The Hoxton invites you to soak up the gorgeous sun rays on their rooftop pool, wine and dine at their three on-site restaurants and bars, and be within walking distance of popular Chicago attractions. The trendy hotel is filled with fine detailed décor and fabulous furnishings. Added bonuses to a stay here include floor-to-ceiling windows, a yoga studio and even a co-working space for those who are travelling for business.
The rooftop is what it’s all about at The Hoxton. You will discover their lively dining experience at the restaurant Cabra, where you can indulge in Peruvian-inspired dishes created by chef Stephanie Izzard, after an afternoon of relaxing around the pool. This hotel makes the list for being one of the best Downtown Chicago hotels with rooftop pools because of its pop of hip stylings and breathtaking views overlooking the city. I would say this is one of the best Downtown Chicago hotels with rooftop pools.
Click here to check out the current rates and availability at The Hoxton, Chicago.
Viceroy Chicago
Viceroy is situated in the exclusive area of the Gold Coast neighbourhood and just steps away from the fantastic shopping, dining and entertainment on the Magnificent Mile – What a location. The interior décor of this hotel is upscale, sleek and stylish, providing you with a luxury stay through their exquisite hospitality. A great feature of this accommodation which is housed in a 120 year old landmark building is its rooftop pool. Surrounded by the city’s skyline you will have stunning views when lounging under the sun. This property rates high when it comes to Downtown Chicago hotels with rooftop pools.
Another great benefit to this rooftop pool is that you are able to order food and drinks to the poolside, meaning you can spend hours here without having to move. Viceroy offers its guests a modern Midwest inspired restaurant, Somerset, where you can be treated to breakfast, lunch and dinner either inside or out on their exterior patio. Keeping fit whilst being away is made easy with their state-of-the-art gym and you can pop around the corner to the Milk + Honey Spa for some rejuvenating treatments.
Click here to check out the current rates and availability at Viceroy Chicago.
The Robey, Chicago, a Member of Design Hotels
The Robey is a historic hotel with a hip twist and part of the world-renowned Design Hotels. Inside this urban hideaway is creative, art-deco stylings that blend modern day trends with past time décor, boasting fabulous on-site amenities and fancy features, ensuring that you have a unique stay. One main moment to love about this hotel is the cool Clever Coyote that is a 90’s inspired bar, serving up tiki drinks, steamed buns and classic sandwiches. It is definitely a spot within the property that you are going to want to hang out in.
Other places on-site include Café Roby with its seasonal comfort food, The Up Room where you will be sitting at one of the highest points for miles, and Canava Club that is part of the rooftop pool. The rooftop pool at The Robey offers a great chill out zone for you to take some time to relax after a fun filled day, with 180 degree views overlooking Downtown Chicago and mouth watering drinks from the bar. You can lounge across the comfortable cushions or take a pew at one of the soft chairs with every area showing off the gorgeous city. Something else to love about this property is its fantastic location which is ideal experience well known attractions.
Click here to check out the current rates and availability at The Robey, Chicago, a Member of Design Hotels.
The Robey, Chicago, a Member of Design Hotels
- Quirky design
- Impressive bar area
- 180 degree city views
DoubleTree by Hilton Chicago Magnificent Mile
In the heart of the city you will find DoubleTree by Hilton that boasts sleek furnishings, modern décor and a chic rooftop pool. Within the hotel you can enjoy HotHouse which is their restaurant for breakfast and dinner, serving delicious dishes in a communal environment paired with refreshing cocktails. There is also another spot to grab food, Made Market, with an on-the-go concept for you to take with you whilst exploring the city or to head up to the rooftop pool with.
After a morning of wandering around top attractions such as Chicago Lakefront Trail, Lake Point Tower and Time Life Building, you can then go up to the rooftop pool for a few hours of downtime. DoubleTree by Hilton has a spacious pool featuring sun loungers around the edge, and providing you with wonderful views looking out at the skyscrapers of Chicago.
Click here to check out the current rates and availability at DoubleTree by Hilton Chicago Magnificent Mile.
DoubleTree by Hilton Chicago Magnificent Mile
- Chic rooftop pool
- Nearby popular attractions
- On-site restaurant
Level Chicago River North
On the doorstep of this luxury accommodation is some of the best shopping in Chicago, so if you are ready to get lost wandering around the stores and fall into a purchasing haven then this is the hotel you will want to stay at. The Level is also surrounded by fabulous galleries, fantastic restaurants and exciting nightlife, meaning you are in a prime location to have a memorable vacation. This property offers its guests the choice between upscale apartments or a boutique hotel, which both show off a sophisticated design and stylish furnishings.
At Level you can soak up the sun on their rooftop pool area, which provides a sanctuary to hide away from the hustle and bustle of the ever moving city. Within the rooftop area you can enjoy a dip in the pool with views overlooking the towering buildings, as well as comfortable cabanas, a family lounge and BBQ grill stations – adding a touch of uniqueness to this space. Other amenities in this hotel include a fitness centre, entertainment spaces, arcade games and meeting rooms, leaving you spoilt for choice when you take a stay here. Another great addition to this property is their on-site sauna and steam room facilities where you can unwind after a busy day of exploring.
Click here to check out the current rates and availability at Level Chicago River North.
Kasa River North Chicago
This accommodation prides itself on providing its guests with a classy, convenient and comfortable stay. Kasa River is housed in a brand new high rise building located between the Old Town and River North. Due to its recent development, the property hosts state-of-the-art amenities, modern design and chic furnishings. The rooms are bright with tall ceilings and large windows, allowing in lots of natural light and great views. All apartments provide you with your own kitchen, so if you don’t feel like leaving the hotel to get food then you can just stay in and cook up your own feast.
As Kasa River has a fantastic location, it means you are also blessed with brilliant views whilst relaxing on one of the sun loungers around their rooftop pool. The area is spacious and gives you the option to soak up the sun or rejuvenate in the shade. More wonderful amenities of this hotel include complimentary toiletries, a business centre, and personalised concierge services.
Click here to check out the current rates and availability at Kasa River North Chicago.
The Penthouse at Grand Plaza
Here you have an upscale top floor apartment with sweeping views overlooking the fabulous Chicago skyline through the floor-to-ceiling windows. You are moments away from the Magnificent Mile and are surrounded by wonderful attractions. The layout at The Penthouse provides you with two bedrooms, a fully equipped kitchen, beautiful dining and living area, plus three separate balconies, you are going to be staying in pure bliss. You will also have access to basketball courts and fitness centre.
The best part about The Penthouse is that you are able to use the rooftop pool and sun terrace. This is going to add that extra bit of luxury to your stay. You can spend hours up here laying underneath the sunrays, going for a few laps in the pool and gazing at the breathtaking city views. The interior of this apartment is stylish, sleek and modern with great furnishings and amenities to ensure that you will have everything on-site which you may need.
Click here to check out the current rates and availability at The Penthouse at Grand Plaza.
Radisson Blu Aqua Hotel, Chicago
Located in the Chicago Loop is the Radisson Blu Aqua Hotel, just moments away from fabulous attractions such as the Chicago Riverwalk, Millennium Public Park and Bridgehouse and Chicago River Museum. This hotel was created with a contemporary design and provides a modern, bright and stylish interior. The rooms offer its guests gorgeous views of Lake Michigan and the lush green parks, with the rooftop pool showing off a 360 view of the city’s skyline. You can also enjoy an outdoor whirlpool alongside being able to swim laps outside on a sunny day.
Their restaurant, FireLake Grill House and Cocktail Bar, will treat you well from a delicious breakfast each morning to fine dining and an aperitif in the evening. They serve up mouth watering farm-to-table dishes of American cuisine. A great highlight of Radisson Blu Aqua Hotel is their on-site spa being steps away from your room. You can relax with high-quality treatments, facials and massages.
Click here to check out the current rates and availability at Radisson Blu Aqua Hotel, Chicago.
Homewood Suites by Hilton Chicago Downtown – Magnificent Mile
Here you have the ideal accommodation if you are looking for a self-catering hotel. At Homewood Suites the rooms are spacious, bright and come well-equipped with a full kitchen. The location of this accommodation is brilliant, it is moments away from premium shopping, great Chicago attractions such as the Museum of Contemporary Art, and even though this is self-catering, each morning you are welcomed to a complimentary hot breakfast.
At Homewood Suites on-site amenities include a rooftop pool, fitness centre and fun activities like their social evenings. The rooftop pool gives you views looking out across the city’s skyline and will be a place for you to escape the hustle and bustle of Downtown Chicago. There is also a pet-friendly policy at this accommodation, so if you need to travel with your furry friends it’s no problem.
Click here to check out the current rates and availability at Homewood Suites by Hilton Chicago Downtown – Magnificent Mile.
Homewood Suites by Hilton Chicago Downtown – Magnificent Mile
- In room full kitchen
- Pet-friendly
- Great location
Hampton Inn Chicago Downtown/Magnificent Mile
Steps away from the Magnificent Mile sits Hampton Inn offering you a great location in the heart of Chicago. Surrounding the hotel are an array of fabulous restaurants as it is next to the dining district and you will also be just moments from the family-friendly theatres. Featured within each suite is a flat screen TV, work desk and coffee maker. Start your day right with their complimentary breakfast before heading out to explore throughout the city.
The rooftop pool at Hampton Inn acts as an oasis away from the busy city life. An afternoon spent up here under the sun, spending time with family and friends, and having a moment to relax is a must. You will get to be in awe of the beautiful Chicago city skyline, which can also be viewed from their cosy fitness room located on the 40th floor.
Click here to check out the current rates and availability at Hampton Inn Chicago Downtown/Magnificent Mile.
Hampton Inn Chicago Downtown/Magnificent Mile
- Heart of the city
- Chicago skyline views
- Complimentary breakfast
And there you have it. The 20 best Downtown Chicago hotels with rooftop pools. All that’s left for you to do is choose one, make the booking, plan which must-do activities you want to check out, pack your bags and have an incredible city getaway experience.
Holiday Inn Hotel & Suites Chicago – Downtown, an IHG Hotel
Within walking distance of Holiday Inn is the famous Downtown Chicago River Loop, and situated opposite is the Old Post Office which is home to an array of well known businesses. Nearby to the hotel are also popular must-see attractions such as the Skydeck at Willis Tower, the Art Institute and the Roosevelt Collection. The rooms at this hotel are a great place to rest and recharge ahead of enjoying all that Chicago has on offer that you will want to check out. The décor is bright and modern, with blackout shades and high-tech amenities.
Another great place to chill out at the Holiday Inn is by their rooftop pool where you can gaze at views overlooking the city, and take a refreshing dip on a sunny day. The area surrounding the pool is spacious and hosts sunbed loungers for you to relax on. Following on from some time spent on their rooftop pool, you can then grab a bite to eat at the on-site restaurant called Fork Fantasy where you can indulge in mouth-watering American dinner dishes and special plates. Within this restaurant you can also start your day right with a delicious breakfast, and for those eager to kick start earlier you can head down to the fully equipped fitness centre.
Click here to check out the current rates and availability at Holiday Inn Hotel & Suites Chicago – Downtown, an IHG Hotel.
Holiday Inn Hotel & Suites Chicago – Downtown, an IHG Hotel
- Fantastic views
- Nearby the River Loop
- Great restaurant
Nobu Hotel Chicago
If you have ever visited the world-renowned restaurant of Nobu then you will already begin to understand the high class level of its hotel. Nobu Hotel offers its guests a luxurious stay filled with brilliant amenities, great facilities and a fantastic location within the city. There are different types of rooms which you can choose from, all providing a comfortable stay, stylish décor and the essentials which you need to have a wonderful stay. The design of the hotel is trendy with unique features and many insta-worthy moments.
Nobu Hotel boasts a handful of stunning restaurants, a tranquil indoor swimming pool and Technogym fitness centre. A main highlight of this hotel is their rooftop terrace. The atmosphere is like an hidden oasis with the furnishings reflecting a romantic environment, making it an ideal spot to hang out on either during the day or of an evening. You can also be treated to a unique dining experience whilst watching over the hustle and bustle of Chicago.
Click here to check out the current rates and availability at Nobu Hotel Chicago.
Loews Chicago Hotel
The best word to describe Loews is luxury. This hotel provides the finest of decor, comfort and services, you will be truly spoiled. You will be staying in the heart of the city, meaning you will have direct access to so many attractions, restaurants and must-see sites. Views from the hotel are overlooking the city and river, providing you with breathtaking moments to soak up. The interior design of this property is sleek, stylish and upscale offering you a sophisticated stay with fantastic amenities.
Loews features several spaces where you can dine and drink, which include the ETA Restaurant and Bar, Lobby Lounge, Streeterville Social and For Five Coffee Roasters, as well as in-room dining options. Two great facilities within this hotel are their spacious and modern indoor lap pool, and rooftop terrace serving up alfresco dining and gorgeous city skyline views, making it a brilliant spot to hang out after a busy day of exploring throughout Chicago. You also have access to a fitness centre, close proximity to the river walk and a delicious breakfast each morning.
Click here to check out the current rates and availability at Loews Chicago Hotel.
The Peninsula Chicago
If you are looking for a 5-star world-class stay then here is where you will want to be. The Peninsula brings a unique twist on a Chicago property as it gives a traditional Asian service blended with the city’s welcoming hospitality. This hotel is well known for being great whether you are travelling for business or leisure, and has been listed in the Forbes Travel Guide 5-Star rating every year since it opened its doors to guests. It is one of the top hotels in Downtown Chicago that you will be impressed with.
Facilities within The Peninsula include a half Olympic size indoor swimming pool, a contemporary gym that provides yoga classes, and a stunning rooftop terrace. The rooftop terrace is perfect to chill out on whilst soaking up the rays from the sun after a fun day of exploring throughout the city that is on your doorstep. You can also enjoy magnificent views overlooking Chicago from the terrace that you will become in awe of. There are also three award-winning restaurants within the hotel offering different types of cuisine that you can treat yourself to each evening.
Click here to check out the current rates and availability at The Peninsula Chicago.
theWit Chicago, a Hilton Hotel
This hotel boasts creative and expressive décor. theWit is located within the centre of Chicago’s theatre district, which is reflected within its design. It provides a contemporary and trendy look featuring pops of colour, adding additional character to the hotel. Sitting throughout the property are unique pieces of artwork which you can admire on your stay. Amenities included in this hotel are fantastic. You will be treated to an in-house restaurant, state-of-the-art gym and gorgeous spa area.
theWit stands separate from other hotels because of its onsite nightclub and rooftop space. These are both award-winning and known to be the best in Chicago. The nightclub and bar has been created to be an impressive spot for entertainment, with the rooftop being newly renovated with a retractable roof making it accessible all year round. In these two places you can enjoy hand crafted cocktails, delicious cuisine and beautiful skyline views.
Click here to check out the current rates and availability at theWit Chicago, a Hilton Hotel.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
The Gwen is a newly renovated upscale hotel that is situated overlooking the famous Michigan Lake. The interior design of this property is breathtaking, the décor is detailed, fancy and glamorous with an art-deco quirk, giving you many insta-worthy moments throughout the hotel. When it comes to luxury facilities this hotel doesn’t fall short of them. You are going to be in awe of their two on-site restaurants, a fantastic fully equipped gym and great business amenities.
The best feature of The Gwen is its rooftop terrace where you will be able to relax with a mouth watering drink in hand, whilst overlooking breathtaking views of the city and keeping warm on an evening with their cosy firepits. Alongside this you can also indulge in delicious cuisine whilst watching the sun go down. Extra benefits to staying here include well-stocked minibar, complimentary toiletries and a work desk with chair in each room.
Click here to check out the current rates and availability at The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
- Glamorous interior design
- Gorgeous rooftop terrace
- Fantastic amenities
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse is always one of the best hotels to stay in when you are looking for a luxurious getaway. On-site amenities include a gorgeous spa where you can indulge in rejuvenating treatments and beauty services, a state-of-the-art equipment filled gym, and a fabulous restaurant serving up local cuisine and cocktails. A highlight of their restaurant is that it is located on their rooftop bar area meaning you can enjoy a mouth-watering dinner whilst watching over the city of Chicago.
The rooms at LondonHouse and interior décor overall is modern with hip features, such as unique furnishings and pops of colour. When it comes to the hotel’s location you will not be disappointed. Within walking distance is the Millennium Park, Time Life Building and the Chicago Riverwalk, so you are in a hot spot to check out these popular attractions. Additional benefits to this property are that it is a boutique hotel, has a concierge service and has a business centre.
Click here to check out the current rates and availability at LondonHouse Chicago, Curio Collection by Hilton.
LondonHouse Chicago, Curio Collection by Hilton
- Steps away from attractions
- Gorgeous spa facilities
- Stunning rooftop terrace
Hyatt Centric The Loop Chicago
The best word to describe the Hyatt Centric is chic due to its furnishings, décor and atmosphere. This hotel is decorated in upscale design with art-deco features and soaked in natural light. A benefit of staying here is that it is also pet-friendly so there’s no need to leave your furry best friends at home when you want to hit the city for a break. Without leaving the hotel you are treated to a 24-hour fitness centre, a contemporary business area with high-tech amenities, and sensational restaurants.
Sitting on top of the Hyatt Centric is a trendy rooftop terrace. Up here you can be wowed by their specialty cocktails, delicious small plates and locally crafted beer. What better way to finalise your day than sipping on a refreshing beverage whilst eating great food and overlooking the city’s skyline as the sun goes down. This hotel is situated in the heart of the famous loop so you are moments away from an array of fantastic attractions, interesting landmarks and wonderful shopping.
Click here to check out the current rates and availability at Hyatt Centric The Loop Chicago.
Godfrey Hotel Chicago
Godfrey is in an ideal location of Downtown Chicago for those who love lively entertainment, fantastic dining options and great shopping. From the hotel you are able to wander around the city by foot and also check out the River North District, with this being a popular property for having a prime location in the Downtown Chicago. The hotel created a design to showcase unique style and a space where everything feels at ease plus comfort. The rooms have modern décor providing a relaxing environment away from the hustle and bustle of Chicago.
Facilities within the Godfrey include the Spa Boutique by Windy City Massage for you to treat yourself to rejuvenating treatments, tech-savvy meeting rooms for those travelling on business, and a fabulous rooftop area with stunning views overlooking the city. The IO Godfrey Roofscape offers an urban oasis where you can indulge in an indoor bar, outside lounge, warm fire pits for cosy nights and a retractable roof on the sunny days. Additional benefits to staying at this hotel are their on-site restaurant, 24 hour fitness centre and floor to ceiling windows.
Click here to check out the current rates and availability at Godfrey Hotel Chicago.
Ivy Boutique Hotel
The Ivy is an adults-only boutique hotel situated in the heart of Downtown Chicago neighbouring the Magnificent Mile and steps away from the exciting sites of the city. You will be treated to spacious rooms with floor-to-ceiling windows and upscale amenities. The interior of the hotel has beautiful dark wood furnishings which adds character to each room, and pops of colour giving it a unique quirk.
Great facilities in the Ivy include the lobby restaurant lounge where you can start your day with a hearty breakfast and finish it with American dishes and hand craft cocktails. There is also a Sky Terrace lounge which is ideal to unwind with a refreshing beverage whilst looking out over the stunning city views. It is possible to get delicious small plates here, and relax in their comfortable lounging area, providing you with a fabulous experience.
Click here to check out the current rates and availability at Ivy Boutique Hotel.
If you are looking to travel to other destinations within America then here are two other blogs you will want to check out when it comes to booking accommodation, 20 Hotels with the BEST Views in Seattle and 13 Best New York Hotels with a View of Central Park.