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40 Best Hotels In Chicago With Rooftop Pool for a Luxury Trip

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Known for its neo-gothic architecture and the beautiful skyline. The Windy City is known to have some of the finest hotels in the country so we have compiled a list of the best hotels in Chicago with (Read More) rooftop pool for a luxurious getaway. These hotels are the best choice to have a picturesque view of the city's skyline.

Here is the list of 40 Hotels In Chicago With Rooftop Pool

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1. Hampton Inn & Suites Chicago-Downtown

Hampton Inn & Suites Chicago-Downtown

Downtown Chicago 300 m from House of Blues Chicago

# 1 in Hotels In Chicago With Rooftop Pool

8.5 /10

(2454 reviews)

Hotel with 11 room options

$ 108 onwards

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2. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Michigan Avenue 500 m from The Magnificent Mile

# 2 in Hotels In Chicago With Rooftop Pool

7.9 /10

(2496 reviews)

The Embassy Suites by Hilton Chicago Downtown Magnificent Mile is a very nice and comfortable hotel (Read More)in Chicago. The staff is friendly and helpful, and the rooms are clean and well-equipped with amenities like a fridge, microwave, and coffee maker. The hotel offers free breakfast with a cook-to-order counter, as well as a fantastic happy hour reception. The location is unbeatable, within walking distance to the Magnificent Mile and the Navy Pier. Overall, the hotel is highly recommended for a pleasant stay in Chicago.

4 star hotel with 19 room options

$ 116 onwards

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3. Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Michigan Avenue 400 m from House of Blues Chicago

# 3 in Hotels In Chicago With Rooftop Pool

7.4 /10

(2209 reviews)

Reviewers Mention: The Hilton Garden Inn Chicago Downtown/Magnificent Mile has a great locati (Read More)on near an L station and in a safe area. The rooms are secure, spacious, and clean, with useful amenities like air conditioning, in-room safe, fridge, and microwave. However, some furniture is dusty and the housekeeping service was lacking, resulting in trash buildup and a shortage of coffee and toilet paper. Overall, it's an average place to stay with friendly staff and good on-site amenities. The location offers many dining options within walking distance.

Hotel with 9 room options

$ 119 onwards

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4. Hilton Chicago

Hilton Chicago

Michigan Avenue 0 m from Hilton Chicago

# 4 in Hotels In Chicago With Rooftop Pool

7.7 /10

(1060 reviews)

Hotel with 30 room options

$ 149 onwards

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5. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

The Loop 600 m from Chicago Riverwalk

# 5 in Hotels In Chicago With Rooftop Pool

7.8 /10

(985 reviews)

The Sheraton Grand Chicago Riverwalk is a beautiful and grand hotel located in downtown Chicago. Wit (Read More)h its excellent location, guests can enjoy stunning views of the pleasure boats on the canal and the downtown area. The hotel offers a wide range of amenities including a spa, indoor swimming pool, fitness center, and business center. The staff is friendly and welcoming, providing exceptional service to make guests feel at home. The rooms are spacious and equipped with standard amenities. The hotel is situated along the riverwalk, offering a great space for walking and enjoying the water. Overall, it is a fantastic choice for both vacationers and business travelers visiting Chicago.

4 star hotel with 18 room options

$ 159 onwards

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6. Embassy Suites Chicago - Downtown

Embassy Suites Chicago - Downtown

Michigan Avenue 400 m from The Magnificent Mile

# 6 in Hotels In Chicago With Rooftop Pool

7.9 /10

(2179 reviews)

Hotel with 9 room options

$ 119 onwards

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7. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Michigan Avenue 200 m from Water Tower Place

# 7 in Hotels In Chicago With Rooftop Pool

8.3 /10

(2912 reviews)

Hotel with 16 room options

$ 121 onwards

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8. Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

The Loop 400 m from Millennium Park

# 8 in Hotels In Chicago With Rooftop Pool

8.1 /10

(1838 reviews)

Want to experience a luxurious stay? Radisson Blu Aqua Hotel Chicago is the one you should be lookin (Read More)g at. Standing tall with its grandeur, it provides sophisticated décor, elegant furnishing and several world class amenities like an outdoor swimming pool, a well maintained garden, a shared lounge, an on- site dining option, a bar and many more. It never fails to satisfy its guests with the best.

4 star hotel with 13 room options

$ 149 onwards

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9. DoubleTree by Hilton Chicago Magnificent Mile

DoubleTree by Hilton Chicago Magnificent Mile

Michigan Avenue 400 m from The Magnificent Mile

# 9 in Hotels In Chicago With Rooftop Pool

8.0 /10

(1414 reviews)

Reviewers Mention: Guests at the DoubleTree by Hilton Chicago Magnificent Mile were impressed (Read More) by the warm cookies offered upon arrival, making them feel at home. Some guests were disappointed with the Hilton Grand Vacation Club, as it was just updated hotel rooms with minimal owner privileges. However, the hotel's location was praised for its convenience and accessibility, surrounded by shops. The cleanliness of the hotel and friendly staff were also highlighted. Some negative aspects mentioned were a broken elevator and difficulty connecting to the TV in the room. Overall, the stay was satisfactory.

4 star hotel with 9 room options

$ 107 onwards

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10. Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

Downtown Chicago 200 m from McCormick Place

# 10 in Hotels In Chicago With Rooftop Pool

8.5 /10

(861 reviews)

Standing tall with all its grandeur and extravagance, Hyatt Regency McCormick Place is definitely on (Read More)e of the most sought after properties in the city that provides lavish accommodations with sophisticated décor and elegant furnishing. Do not miss out on the world class amenities like an indoor swimming pool, a fitness centre, a 24 hour front desk service and many more to ensure a pleasant and comfortable stay to its guests.

4 star hotel with 13 room options

$ 151 onwards

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11. Park Hyatt Chicago

Park Hyatt Chicago

Michigan Avenue 200 m from Water Tower Place

# 11 in Hotels In Chicago With Rooftop Pool

9.2 /10

(61 reviews)

Enjoy a vast array of amenities like an indoor swimming pool, a fitness centre with modern equipment (Read More), a spa providing rejuvenating massages and treatments, a 24 hour front desk service, an on- site dining option serving delicious dishes from different cuisines and many more at Park Hyatt Chicago. Make memories that will be cherished for years to come at this luxurious property with your friends and family.

5 star hotel with 14 room options

$ 435 onwards

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12. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

The Loop 200 m from Chicago Riverwalk

# 12 in Hotels In Chicago With Rooftop Pool

9.0 /10

(1411 reviews)

Located within 1 km of Bridgehouse and Chicago River Museum, House Of Blues Chicago, Chicago Tribune (Read More) Towers and many more popular attractions, Trump International Hotel & Tower Chicago is one of the most sought after properties in the city. Feel comfortable and welcome by the well trained and friendly staff who provide excellent service in addition to out of the world facilities and amenities that the property provides.

5 star hotel with 15 room options

$ 425 onwards

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13. Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Michigan Avenue 200 m from The Magnificent Mile

# 13 in Hotels In Chicago With Rooftop Pool

8.3 /10

(675 reviews)

The Hyatt group of hotels have gained the trust of its guests for years, Hyatt Centric Chicago Magni (Read More)ficent Mile falling within that group also does not disappoint its guests. Luxurious décor with several amenities like an indoor swimming pool, a fitness centre, on- site dining options and many more have stolen the show. Do not forget to avail all these amenities and enjoy a pleasant stay at the property.

4 star hotel with 10 room options

$ 104 onwards

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14. The Langham Chicago

The Langham Chicago

The Loop 100 m from Chicago Riverwalk

# 14 in Hotels In Chicago With Rooftop Pool

9.3 /10

(345 reviews)

Boasting of luxurious accommodations with heavenly bed, French windows and a number of necessary fac (Read More)ilities, The Langham Chicago is preferred by many. It also provides amenities like an indoor swimming pool, a well equipped fitness centre, an on- site dining option and many more. Venture out and explore the popular attractions surrounding the property in addition to several delicious eateries and shopping malls and popular pubs.

5 star hotel with 22 room options

$ 361 onwards

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15. Viceroy Chicago

Viceroy Chicago

Downtown Chicago 300 m from Clark/Division Station

# 15 in Hotels In Chicago With Rooftop Pool

9.0 /10

(1482 reviews)

Visiting Chicago this vacation and looking for a property that will provide you with the elegant and (Read More) distinguished accommodations? Viceroy Chicago has got exactly that for you. Boasting of an outdoor swimming pool, a state of the art fitness centre, several delicious on- site dining options, a 24 hour front desk service and many more amenities, this property is sought after by several guests.

5 star hotel with 15 room options

$ 245 onwards

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16. Loews Chicago Hotel

Loews Chicago Hotel

The Loop 600 m from The Magnificent Mile

# 16 in Hotels In Chicago With Rooftop Pool

9.1 /10

(1618 reviews)

Featuring an indoor swimming pool, a fitness centre, on- site dining options, a 24 hour front desk s (Read More)ervice and many more amenities, Loews Chicago Hotel has won several hearts over the years. Distinguished and classy accommodations with sophisticated décor and elegant furnishing have also been positively reviewed by many. Do not forget to explore the surrounding of the property as it is filled with popular attractions and eateries.

4 star hotel with 13 room options

$ 229 onwards

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17. AC Hotel Chicago Downtown

AC Hotel Chicago Downtown

Michigan Avenue 200 m from The Magnificent Mile

# 17 in Hotels In Chicago With Rooftop Pool

8.4 /10

(570 reviews)

Located at the heart of the city of Chicago, AC Hotel Chicago Downtown is not only popular for its e (Read More)xcellent location, but also for its out of the world amenities like a heated indoor swimming pool, a well equipped fitness centre, a 24 hour front desk service, a huge event space, a shared lounge, a bar and many more. Suitable for all kinds of guests and occasions.

4 star hotel with 8 room options

$ 129 onwards

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18. Best Western River North Hotel

Best Western River North Hotel

Downtown Chicago 400 m from Moes Cantina River North

# 18 in Hotels In Chicago With Rooftop Pool

7.5 /10

(2080 reviews)

Featuring an indoor swimming pool, a fitness centre, a 24 hour front desk service, a shared lounge, (Read More)an on- site dining option and many more amenities, Best Western River North Hotel is preferred by many. Not only has it been positively reviewed for its amenities and facilities, but also for the excellent location that it provides. It is surrounded by several eateries and attractions like Blue Chicago, Shops at Northbridge, Chicago Riverwalk etc.

Hotel with 12 room options

$ 93 onwards

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19. Hampton Inn by Hilton Chicago Downtown West Loop

Hampton Inn by Hilton Chicago Downtown West Loop

Downtown Chicago 800 m from Sears Tower

# 19 in Hotels In Chicago With Rooftop Pool

8.6 /10

(805 reviews)

Standing tall in the ehart of Chicago with all its grandeur and extravagance, Hampton Inn by Hilton (Read More)Chicago Downtown West Loop is perfect for those looking for a luxurious stay experience with the best of facilities and amenities. In addition to that enjoy spacious accommodations with sophisticated furnishing, heavenly beds and excellent service by the well trained and friendly staff who make the guests feel at home and make it worth every penny.

Hotel with 13 room options

$ 140 onwards

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20. W Chicago - Lakeshore

W Chicago - Lakeshore

Downtown Chicago 600 m from Navy Pier

# 20 in Hotels In Chicago With Rooftop Pool

7.9 /10

(1641 reviews)

Make memories with your loved ones while your visit to Lakeshore at W Chicago – Lakeshore or e (Read More)njoy a good night’s sleep after a long day of work if you are visiting for a business trip. Suitable for all kinds of guests, the hotel is one of the most sought after properties in the city. It features a fitness centre, outdoor swimming pool, on- site dining options and many more amenities.

4 star hotel with 12 room options

$ 169 onwards

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21. Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Michigan Avenue 300 m from The Magnificent Mile

# 21 in Hotels In Chicago With Rooftop Pool

8.2 /10

(2045 reviews)

Relax on the sun loungers that surround the indoor swimming pool, or in the shared lounge area. You (Read More)can also choose to hit the fitness centre, or enjoy a delicious meal at the on- site dining option. If you are visiting Chicago for a business trip, Aloft Chicago Mag Mile will not disappoint you as it provides with a business centre as well.

Hotel with 8 room options

$ 99 onwards

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22. The Peninsula Chicago

The Peninsula Chicago

Michigan Avenue 200 m from The Magnificent Mile

# 22 in Hotels In Chicago With Rooftop Pool

9.3 /10

(237 reviews)

In less than 1 km from The Peninsula Chicago, the guests can enjoy the Michigan Avenue, Water Tower (Read More)Chicago, Chicago Museum of Contemporary Art and several other top attractions of the city. Dive into the indoor swimming pool, or enjoy a guilt free delicious meal at the on- site dining option after hitting the gym for the daily fitness regime, it has got something for all the guests.

5 star hotel with 11 room options

$ 475 onwards

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23. Courtyard by Marriott Chicago Downtown/River North

Courtyard by Marriott Chicago Downtown/River North

The Loop 200 m from House of Blues Chicago

# 23 in Hotels In Chicago With Rooftop Pool

7.9 /10

(367 reviews)

Looking for a luxurious stay while you visit Chicago? Courtyard by Marriott Chicago Downtown/River N (Read More)orth is where you should be looking at. It will not be wrong to term it as the epitome of luxury with the spacious accommodations that it provides which are equipped with heavenly beds, elegant décor and sophisticated furnishing. Stroll around the well maintained garden, or enjoy a delicious meal at the on- site restaurant.

Hotel with 11 room options

$ 125 onwards

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24. Holiday Inn Chicago Mart Plaza River North

Holiday Inn Chicago Mart Plaza River North

The Loop 200 m from House of Blues Chicago

# 24 in Hotels In Chicago With Rooftop Pool

8.7 /10

(19 reviews)

Reviewers Mention: Guests had an amazing experience at the Residence Inn Chicago Downtown/Riv (Read More)er North. They praised the friendly and accommodating staff, excellent breakfast options, spacious rooms, and convenient location near attractions. The hotel offered packages and EV charging, and the rooms were quiet and clean. Overall, it was a great stay and highly recommended.

$ 217 onwards

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25. SpringHill Suites Chicago Downtown/River North

SpringHill Suites Chicago Downtown/River North

The Loop 200 m from House of Blues Chicago

# 25 in Hotels In Chicago With Rooftop Pool

8.6 /10

(864 reviews)

Planning to visit Chicago this vacation? SpringHill Suites Chicago Downtown/River North is one of th (Read More)e most sought after properties in the city. Spacious rooms with heavenly beds, French windows to enjoy the view of the city and several necessary facilities are preferred by many. Hit the fitness centre, or venture out to explore the city to its fullest by visiting the nearby popular attractions like Millennium Station.

Hotel with 7 room options

$ 120 onwards

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26. The Robey

The Robey

Lincoln Park 0 m from Wicker Park

# 26 in Hotels In Chicago With Rooftop Pool

8.6 /10

(327 reviews)

Surrounded by top attractions like Wicker Park, Congress Theater and many more, The Robey is one of (Read More)the most sought after properties that falls within a close periphery of delicious eateries, parks with greenery, lavish shopping malls and many other interesting places. Visiting for a business trip or a leisure trip, this elegant property welcomes all kinds of guests with open arms. Relax in the comfort that it provides.

4 star hotel with 14 room options

$ 144 onwards

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27. Residence Inn by Marriott Chicago Downtown/River North

Residence Inn by Marriott Chicago Downtown/River North

The Loop 200 m from House of Blues Chicago

# 27 in Hotels In Chicago With Rooftop Pool

8.6 /10

(333 reviews)

Surrounded by popular attractions like Millennium Station, Millennium Park, Marina City and many mor (Read More)e, along with several delicious eateries, lavish shopping malls and other interesting places, Residence Inn by Marriott Chicago Downtown/River North provides an excellent location for its guests to explore. It also provides amenities like the fitness centre, a shared lounge, a business centre, a 24 hour front desk service and many more.

Hotel with 5 room options

$ 130 onwards

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28. InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

Michigan Avenue 400 m from The Magnificent Mile

# 28 in Hotels In Chicago With Rooftop Pool

8.0 /10

(491 reviews)

Looking for a property that is suitable for all kinds of guests? InterContinental Chicago Magnificen (Read More)t Mile, an IHG Hotel is the one you should be looking at. Providing a 24 hour business centre and event space, it attracts those visiting Chicago for a business trip and with amenities like an indoor swimming pool, lavish on- site dining options, it attracts those visiting on a leisure trip.

4 star hotel with 15 room options

$ 148 onwards

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29. Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

Beverly 6.5 kms from Holy Cross Hospital

# 29 in Hotels In Chicago With Rooftop Pool

7.6 /10

(663 reviews)

Featuring 2 on- site dining options, an indoor swimming pool, a fitness centre, a business centre, a (Read More) 24 hour front desk service and many more amenities, Hilton Chicago/Oak Lawn provides one of the most luxurious stays to those visiting Chicago, irrespective of whether for a business trip or for a vacation with friends or family or on a solo trip. Make memories that will last for years to come.

Hotel with 6 room options

$ 131 onwards

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30. Courtyard Chicago Downtown/Magnificent Mile

Courtyard Chicago Downtown/Magnificent Mile

Michigan Avenue 200 m from The Magnificent Mile

# 30 in Hotels In Chicago With Rooftop Pool

8.3 /10

(520 reviews)

Boasting of an indoor swimming pool, an on- site dining option, a 24 hour front desk service and sev (Read More)eral other amenities, Courtyard Chicago Downtown/Magnificent Mile has won several hearts over the years. It has also been positively reviewed for its hospitality and out of the world service provided by the well trained and friendly staff who make the guests feel warm and at home.

4 star hotel with 18 room options

$ 115 onwards

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31. Homewood Suites by Hilton Chicago Downtown West Loop

Homewood Suites by Hilton Chicago Downtown West Loop

Downtown Chicago 800 m from Sears Tower

# 31 in Hotels In Chicago With Rooftop Pool

8.9 /10

(517 reviews)

Looking for a home away home? Classy interior with the best of facilities have won several hearts ov (Read More)er the years. Spacious accommodations with French windows to enjoy the breath taking view of the city, heavenly beds which provides the utmost comfort offers a pleasant and out of the world stay experience. Do not miss out on the amenities like the fitness centre, a bar, a business centre and many more.

Hotel with 7 room options

$ 149 onwards

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32. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

The Loop 300 m from East-West University

# 32 in Hotels In Chicago With Rooftop Pool

8.2 /10

(397 reviews)

Whether you are spending the entire day venturing out to explore the city or relaxing in the luxury (Read More)property, Hilton Garden Inn Chicago Downtown South Loop offers spacious accommodations with heavenly and comfortable beds that is perfect for a good night’s sleep. Do not miss out on the French windows that the rooms are equipped with which provides an alluring view of the city.

Hotel with 11 room options

$ 84 onwards

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33. Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

The Loop 300 m from wndr museum

# 33 in Hotels In Chicago With Rooftop Pool

8.4 /10

(654 reviews)

In addition to providing the best location with several delicious eateries, lavish shopping malls, a (Read More)nd top attractions surrounding this gorgeous and luxurious property, Hyatt House Chicago West Loop is a 3 star accommodation that provides amenities like an indoor swimming pool, an on- site bar, a fitness centre, an on- site dining option, a 24 hour front desk and many more.

Hotel with 14 room options

$ 103 onwards

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34. Homewood Suites By Hilton Chicago Downtown South Loop

Homewood Suites By Hilton Chicago Downtown South Loop

The Loop 300 m from East-West University

# 34 in Hotels In Chicago With Rooftop Pool

8.3 /10

(726 reviews)

This 3 star property stands tall with its elegance in the city of Chicago and provides appealing roo (Read More)ms with the best of facilities and the maximum comfort. Homewood Suites By Hilton Chicago Downtown South Loop is worth every penny being spent on it and is a perfect place to make memories with your friends and family that you will cherish for years to come.

Hotel with 8 room options

$ 95 onwards

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35. Hampton Inn Chicago McCormick Place

Hampton Inn Chicago McCormick Place

Michigan Avenue 200 m from Wintrust Arena

# 35 in Hotels In Chicago With Rooftop Pool

8.4 /10

(908 reviews)

Boasting of a rejuvenating indoor swimming pool, a fitness centre with several modern equipment, a 2 (Read More)4 hour front desk service, an on- site dining option serving delicious dishes, this 3 star property has been positively reviewed by many. You can choose to relax in the comfortable accommodations with the best of facilities or venture out to explore the city to its fullest by visiting the nearby popular attractions.

Hotel with 9 room options

$ 84 onwards

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36. Waldorf Astoria Chicago

Waldorf Astoria Chicago

Michigan Avenue 300 m from Fourth Presbyterian Church

# 36 in Hotels In Chicago With Rooftop Pool

8.5 /10

(114 reviews)

Exquisite décor, sophisticated and classy furnishing has made Waldorf Astoria Chicago quite p (Read More)opular among the guests. Providing on- site dining options, spa and wellness centre that provides rejuvenating massages and treatments, an indoor swimming pool and several other amenities, the property has stolen several hearts and provides a lavish and comfortable stay experience to all its guests. Relax and rejuvenate yourself at this luxurious hotel.

5 star hotel with 13 room options

$ 423 onwards

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37. Home2 Suites By Hilton Chicago McCormick Place

Home2 Suites By Hilton Chicago McCormick Place

Michigan Avenue 200 m from Wintrust Arena

# 37 in Hotels In Chicago With Rooftop Pool

8.6 /10

(308 reviews)

Surrounded by attractions like Glessner House Museum, Arie Crown Theater, and many more, Home2 Suite (Read More)s By Hilton Chicago McCormick Place provides an excellent location for its guests to explore in the city. You can also choose to enjoy the breath taking view of the beautiful city of Chicago from your spacious accommodations tucked in the comfortable beds and enjoying the several necessary and modern facilities.

Hotel with 7 room options

$ 93 onwards

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38. Four Seasons Chicago

Four Seasons Chicago

Michigan Avenue 100 m from Fourth Presbyterian Church

# 38 in Hotels In Chicago With Rooftop Pool

8.9 /10

(167 reviews)

With French décor and classy furnishing, Four Seasons Chicago offers with spacious and luxuri (Read More)ous accommodations equipped with comfortable beds, French windows and a number of necessary and modern facilities that make it a pleasant stay experience. Do not miss out on the vast array of amenities that the property provides with like an indoor swimming pool, a spa and wellness centre and many more.

5 star hotel with 21 room options

$ 355 onwards

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39. Hilton Garden Inn Chicago McCormick Place

Hilton Garden Inn Chicago McCormick Place

Michigan Avenue 200 m from Wintrust Arena

# 39 in Hotels In Chicago With Rooftop Pool

8.0 /10

(318 reviews)

If you are visiting Chicago this vacation and looking for a property that will provide you with luxu (Read More)ry at its best then you are in luck. Hilton Garden Inn Chicago McCormick Place has got the best of amenities and facilities all under the same roof for its guests. Enjoy a host of amenities like an indoor swimming, or venture out to explore the eateries, and the top attractions that surround the property.

Hotel with 9 room options

$ 84 onwards

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40. Holiday Inn Hotel & Suites Chicago - Downtown, an IHG Hotel

Holiday Inn Hotel & Suites Chicago - Downtown, an IHG Hotel

Downtown Chicago 600 m from Sears Tower

# 40 in Hotels In Chicago With Rooftop Pool

7.9 /10

(472 reviews)

Dive into the outdoor swimming pool, or relax on the sun loungers surrounding it, or enjoy a guilt f (Read More)ree delicious meal at the on- site dining options after hitting the gym for the daily fitness regime, or relax at the shared lounge area, Holiday Inn Hotel & Suites Chicago - Downtown, an IHG Hotel provides with a number of activities. Rejuvenate yourself in the comfort of the property.

Hotel with 9 room options

$ 113 onwards

View Deal >

Which of these fantastic hotels in Chicago with rooftop pools are you most excited about visiting? Let us know in the comments below.

No more curated options for Best Hotels In Chicago With Rooftop Pool for a Luxury Trip

However, you can try some of these similar properties.

1. The Palmer House Hilton

The Palmer House Hilton

The Loop 100 m from Adams/Wabash Station

7.5

(968 reviews)

Facilities: Bar, Wifi, Spa, Pets Allowed, Pool, Concierge Service, Food

4 star hotel with 17 room options

$144 onwards

View Deal >

2. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

The Loop 100 m from University Club of Chicago

8.7

(1015 reviews)

The Silversmith Hotel Chicago Downtown is a historic hotel located in the heart of Chicago. It offer (Read More)s comfortable and spacious rooms, impeccable cleanliness, and friendly and welcoming staff. The hotel is centrally located, within walking distance of famous landmarks, and has easy access to public transportation. The hotel features a restaurant and bar, a fitness center, a business center, laundry facilities, and free WiFi. With its great location, excellent service, and attractive amenities, the Silversmith Hotel is a top choice for travelers visiting Chicago.

4 star hotel with 9 room options

$119 onwards

View Deal >

3. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

The Loop 300 m from Lollapalooza CHICAGO

8.3

(1114 reviews)

Providing amenities like event spaces with business amenities, Hyatt Centric The Loop Chicago is sui (Read More)table for those visiting Chicago for a business trip. In addition to that, this luxurious property is also suitable for those on a leisure trip with amenities like a fitness centre, a rooftop bar, a swimming pool and many more. It also provides classy accommodations with heavenly bed for a good night’s sleep.

4 star hotel with 10 room options

$111 onwards

View Deal >

4. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District

The Loop 300 m from Adams/Wabash Station

8.5

(947 reviews)

Located in the heart of Chicago, the Hampton Inn Majestic Chicago Theatre District offers a range of (Read More) amenities, including parking, a fitness center, a business center, and free WiFi. The hotel is housed in a beautiful building and boasts an excellent location, just steps away from famous landmarks such as Millennium Park. The hotel staff receive high praise for their exceptional service and friendliness. The rooms are impeccably clean and well-maintained, and the complimentary breakfast is highly recommended. Overall, the hotel provides a pleasant and secure stay in Chicago.

Hotel with 6 room options

$107 onwards

View Deal >

5. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

The Loop 500 m from Chicago Riverwalk

8.1

(1178 reviews)

Facilities: Bar, Wifi, Pets Allowed, Food

4 star hotel with 13 room options

$139 onwards

View Deal >

6. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

The Loop 100 m from Chicago Riverwalk

8.9

(870 reviews)

Want property that will provide you with a tri level bar? LondonHouse Chicago, Curio Collection by H (Read More)ilton is one of those luxurious properties that offers exactly the same. Sitting along the Chicago River, it provides accommodations with a mesmerizing view. Suitable for those on a business trip with a business centre as well as for those on a leisure trip with a ballet bar, fitness centre and many more amenities.

4 star hotel with 15 room options

$140 onwards

View Deal >

7. Hotel Chicago Downtown, Autograph Collection

Hotel Chicago Downtown, Autograph Collection

The Loop 0 m from House of Blues Chicago

8.6

(873 reviews)

Reviewers Mention: Review 1: While the rooms at the Hotel Chicago Downtown, Autograph Collect (Read More)ion are in need of a refresh, the value for the points paid was good. The bartender and the check-in staff were fantastic. Overall, the stay was satisfactory and the reviewer would return on another points stay. Review 2: The reviewer loved their stay at the hotel, praising the friendly staff, clean and comfortable room, and the added perks like an upgrade and free tickets to the Chicago sports museum. They enjoyed room service and the location was perfect. They would definitely return to the hotel. Review 3: The reviewer found the room to be spacious and nice, but the bathroom was outdated and in need of renovation. The concierge lounge was outstanding and had great breakfast. The wings at the bar were the best they've had. The staff provided excellent customer service. The noise from the street and other rooms was a minor inconvenience. The location was great and the nearby restaurant Yolk was awesome. Review 4: The rooms at the hotel were updated, clean, and comfortable. The location was convenient with plenty of nearby dining options. The rooms and bathrooms were spacious. High-level Marriott Bonvoy members can enjoy free breakfast in the lounge. The staff were all very nice. Overall, the reviewers mentioned the need for room renovations, but appreciated the good value for points, excellent customer service, clean rooms, great amenities, and convenient location of the Hotel Chicago Downtown, Autograph Collection.

4 star hotel with 4 room options

$116 onwards

View Deal >

8. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

The Loop 300 m from The Chicago Theatre

8.8

(1225 reviews)

Staypineapple, An Iconic Hotel located in The Loop, Chicago, offers a unique and enjoyable experienc (Read More)e with its old-style charm and modern amenities. The hotel's customer service is top-notch, with friendly staff who go above and beyond to make guests feel comfortable. The rooms are well-equipped, cozy, and beautifully designed, with all the necessary amenities. The hotel is in a great location, within walking distance of popular landmarks such as Millennium Park and Michigan Avenue. The hotel offers free WiFi, a fitness center, and a bar, among other amenities.

4 star hotel with 10 room options

$119 onwards

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9. 21c Museum Hotel Chicago

21c Museum Hotel Chicago

Michigan Avenue 200 m from The Magnificent Mile

8.4

(1052 reviews)

Facilities: Bar, Wifi, Pets Allowed, Food

4 star hotel with 12 room options

$107 onwards

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10. Swissotel Chicago

Swissotel Chicago

The Loop 500 m from Millennium Park

8.5

(879 reviews)

Facilities: Bar, Wifi, Pets Allowed, Concierge Service, Food

4 star hotel with 29 room options

$127 onwards

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11. The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

Michigan Avenue 300 m from House of Blues Chicago

8.5

(1168 reviews)

Reviewers Mention: The Royal Sonesta Chicago River North receives positive reviews for its ex (Read More)cellent service and beautiful rooms. Some guests note the need for improved cleanliness in the rooms but are still willing to return due to the overall experience. The hotel is praised for its friendly staff and attention to detail. Guests appreciate the jacuzzi suite, helpful front desk, and enjoyable dining experiences. The hotel is also commended for accommodating flight delays and providing thoughtful birthday surprises. The location is convenient for shopping and dining, and guests would stay here again.

4 star hotel with 16 room options

$139 onwards

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Top Hotel Collections In Chicago

Near Shedd Aquarium

Near Shedd Aquarium

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Near The Art Institute of Chicago

Near The Art Institute of Chicago

Hotels Near The Art Institute of Chicago
Near Millennium Park

Near Millennium Park

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Near Soldier Field

Near Soldier Field

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Near DePaul University

Near DePaul University

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Near McCormick Place

Near McCormick Place

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Near Loyola University Chicago

Near Loyola University Chicago

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Near Guaranteed Rate Field

Near Guaranteed Rate Field

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Near House of Blues Chicago

Near House of Blues Chicago

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Near Wintrust Arena

Near Wintrust Arena

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Best time for a staycation in Chicago?

The most popular time, weather-wise, to visit Chicago spans through April and June when the spring season makes its entry after a chilling winter season. Another popular time to visit Chicago is between September and November when the fall season is at its peak, and the temperature is perfect for outdoor activities. During these times of the year, you will also find a plethora of cultural events and local festivals in the city. In general, summertime (from June to August) is more popular among tourists to visit Chicago than winters (November to March). However, the boarding and lodging rates can be very steep in the summertime, and tourists may find great discounts on hotels during the winter season.
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