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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

(1914 reviews)

Hotel with 11 room options

$ 92 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

8.0 /10

(2751 reviews)

The Embassy Suites by Hilton Chicago Downtown Magnificent Mile is a very nice and comfortable hotel in Chicago. The staff is friendly and helpful, and the rooms are clean and well-equipped with amenit (Read More)ies 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

$ 102 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

7.3 /10

(1695 reviews)

Hotel with 9 room options

$ 88 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

7.9 /10

(790 reviews)

4 star hotel with 31 room options

$ 135 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

7.9 /10

(1096 reviews)

The Sheraton Grand Chicago Riverwalk is a beautiful and grand hotel located in downtown Chicago. With its excellent location, guests can enjoy stunning views of the pleasure boats on the canal and the (Read More) 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 16 room options

$ 129 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

7.6 /10

(1430 reviews)

4 star hotel with 9 room options

$ 101 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

(2719 reviews)

4 star hotel with 16 room options

$ 118 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

8.0 /10

(1795 reviews)

Want to experience a luxurious stay? Radisson Blu Aqua Hotel Chicago is the one you should be looking at. Standing tall with its grandeur, it provides sophisticated décor, elegant furnishing an (Read More)d 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 12 room options

$ 118 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

8.1 /10

(1121 reviews)

4 star hotel with 10 room options

$ 92 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

8.4 /10

(891 reviews)

Standing tall with all its grandeur and extravagance, Hyatt Regency McCormick Place is definitely one of the most sought after properties in the city that provides lavish accommodations with sophistic (Read More)ated 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

$ 170 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

8.8 /10

(74 reviews)

Enjoy a vast array of amenities like an indoor swimming pool, a fitness centre with modern equipment, a spa providing rejuvenating massages and treatments, a 24 hour front desk service, an on- site di (Read More)ning 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 15 room options

$ 373 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

(1146 reviews)

Located within 1 km of Bridgehouse and Chicago River Museum, House Of Blues Chicago, Chicago Tribune Towers and many more popular attractions, Trump International Hotel & Tower Chicago is one of t (Read More)he 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 72 room options

$ 318 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

8.4 /10

(754 reviews)

The Hyatt group of hotels have gained the trust of its guests for years, Hyatt Centric Chicago Magnificent Mile falling within that group also does not disappoint its guests. Luxurious décor wi (Read More)th 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 11 room options

$ 127 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

(352 reviews)

Boasting of luxurious accommodations with heavenly bed, French windows and a number of necessary facilities, The Langham Chicago is preferred by many. It also provides amenities like an indoor swimmin (Read More)g 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

$ 405 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

(1606 reviews)

Visiting Chicago this vacation and looking for a property that will provide you with the elegant and distinguished accommodations? Viceroy Chicago has got exactly that for you. Boasting of an outdoor (Read More)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 16 room options

$ 178 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

8.9 /10

(1447 reviews)

Featuring an indoor swimming pool, a fitness centre, on- site dining options, a 24 hour front desk service and many more amenities, Loews Chicago Hotel has won several hearts over the years. Distingui (Read More)shed 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

$ 134 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

8.3 /10

(648 reviews)

Located at the heart of the city of Chicago, AC Hotel Chicago Downtown is not only popular for its excellent location, but also for its out of the world amenities like a heated indoor swimming pool, a (Read More) 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

$ 101 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

(1771 reviews)

Featuring an indoor swimming pool, a fitness centre, a 24 hour front desk service, a shared lounge, an on- site dining option and many more amenities, Best Western River North Hotel is preferred by ma (Read More)ny. 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 11 room options

$ 85 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

8.5 /10

(871 reviews)

Standing tall in the ehart of Chicago with all its grandeur and extravagance, Hampton Inn by Hilton Chicago Downtown West Loop is perfect for those looking for a luxurious stay experience with the bes (Read More)t 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

$ 109 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

(1586 reviews)

Make memories with your loved ones while your visit to Lakeshore at W Chicago – Lakeshore or enjoy a good night’s sleep after a long day of work if you are visiting for a business trip. Su (Read More)itable 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

$ 127 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

8.1 /10

(1927 reviews)

Relax on the sun loungers that surround the indoor swimming pool, or in the shared lounge area. You can also choose to hit the fitness centre, or enjoy a delicious meal at the on- site dining option. (Read More)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

$ 92 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

9.5 /10

(193 reviews)

In less than 1 km from The Peninsula Chicago, the guests can enjoy the Michigan Avenue, Water Tower Chicago, Chicago Museum of Contemporary Art and several other top attractions of the city. Dive into (Read More) 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

7.7 /10

(425 reviews)

Looking for a luxurious stay while you visit Chicago? Courtyard by Marriott Chicago Downtown/River North is where you should be looking at. It will not be wrong to term it as the epitome of luxury wit (Read More)h 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 9 room options

$ 110 onwards

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24. SpringHill Suites Chicago Downtown/River North

SpringHill Suites Chicago Downtown/River North

The Loop 200 m from House of Blues Chicago

# 24 in Hotels In Chicago With Rooftop Pool

8.3 /10

(731 reviews)

Planning to visit Chicago this vacation? SpringHill Suites Chicago Downtown/River North is one of the most sought after properties in the city. Spacious rooms with heavenly beds, French windows to enj (Read More)oy 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

$ 103 onwards

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25. The Robey

The Robey

Lincoln Park 0 m from Wicker Park

# 25 in Hotels In Chicago With Rooftop Pool

8.7 /10

(353 reviews)

Surrounded by top attractions like Wicker Park, Congress Theater and many more, The Robey is one of the most sought after properties that falls within a close periphery of delicious eateries, parks wi (Read More)th 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 20 room options

$ 131 onwards

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26. 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

# 26 in Hotels In Chicago With Rooftop Pool

8.4 /10

(380 reviews)

Surrounded by popular attractions like Millennium Station, Millennium Park, Marina City and many more, along with several delicious eateries, lavish shopping malls and other interesting places, Reside (Read More)nce 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 4 room options

$ 109 onwards

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27. InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

Michigan Avenue 400 m from The Magnificent Mile

# 27 in Hotels In Chicago With Rooftop Pool

8.0 /10

(516 reviews)

Looking for a property that is suitable for all kinds of guests? InterContinental Chicago Magnificent Mile, an IHG Hotel is the one you should be looking at. Providing a 24 hour business centre and ev (Read More)ent 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

$ 143 onwards

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28. Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

Beverly 6.5 kms from Holy Cross Hospital

# 28 in Hotels In Chicago With Rooftop Pool

7.7 /10

(622 reviews)

Featuring 2 on- site dining options, an indoor swimming pool, a fitness centre, a business centre, a 24 hour front desk service and many more amenities, Hilton Chicago/Oak Lawn provides one of the mos (Read More)t 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

$ 113 onwards

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29. Courtyard Chicago Downtown/Magnificent Mile

Courtyard Chicago Downtown/Magnificent Mile

Michigan Avenue 200 m from The Magnificent Mile

# 29 in Hotels In Chicago With Rooftop Pool

8.2 /10

(461 reviews)

Boasting of an indoor swimming pool, an on- site dining option, a 24 hour front desk service and several other amenities, Courtyard Chicago Downtown/Magnificent Mile has won several hearts over the ye (Read More)ars. 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 17 room options

$ 92 onwards

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30. Homewood Suites by Hilton Chicago Downtown West Loop

Homewood Suites by Hilton Chicago Downtown West Loop

Downtown Chicago 800 m from Sears Tower

# 30 in Hotels In Chicago With Rooftop Pool

8.7 /10

(434 reviews)

Looking for a home away home? Classy interior with the best of facilities have won several hearts over the years. Spacious accommodations with French windows to enjoy the breath taking view of the cit (Read More)y, 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

$ 118 onwards

View Deal >

31. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

The Loop 300 m from East-West University

# 31 in Hotels In Chicago With Rooftop Pool

8.1 /10

(602 reviews)

Whether you are spending the entire day venturing out to explore the city or relaxing in the luxury property, Hilton Garden Inn Chicago Downtown South Loop offers spacious accommodations with heavenly (Read More) 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

View Deal >

32. Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

The Loop 300 m from wndr museum

# 32 in Hotels In Chicago With Rooftop Pool

8.5 /10

(717 reviews)

In addition to providing the best location with several delicious eateries, lavish shopping malls, and top attractions surrounding this gorgeous and luxurious property, Hyatt House Chicago West Loop i (Read More)s 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

$ 122 onwards

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33. Homewood Suites By Hilton Chicago Downtown South Loop

Homewood Suites By Hilton Chicago Downtown South Loop

The Loop 300 m from East-West University

# 33 in Hotels In Chicago With Rooftop Pool

7.9 /10

(1107 reviews)

This 3 star property stands tall with its elegance in the city of Chicago and provides appealing rooms with the best of facilities and the maximum comfort. Homewood Suites By Hilton Chicago Downtown S (Read More)outh 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 9 room options

$ 96 onwards

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34. Hampton Inn Chicago McCormick Place

Hampton Inn Chicago McCormick Place

Michigan Avenue 200 m from Wintrust Arena

# 34 in Hotels In Chicago With Rooftop Pool

8.3 /10

(918 reviews)

Boasting of a rejuvenating indoor swimming pool, a fitness centre with several modern equipment, a 24 hour front desk service, an on- site dining option serving delicious dishes, this 3 star property (Read More)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

$ 75 onwards

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35. Waldorf Astoria Chicago

Waldorf Astoria Chicago

Michigan Avenue 300 m from Fourth Presbyterian Church

# 35 in Hotels In Chicago With Rooftop Pool

8.3 /10

(156 reviews)

Exquisite décor, sophisticated and classy furnishing has made Waldorf Astoria Chicago quite popular among the guests. Providing on- site dining options, spa and wellness centre that provides re (Read More)juvenating 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 14 room options

$ 450 onwards

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36. Home2 Suites By Hilton Chicago McCormick Place

Home2 Suites By Hilton Chicago McCormick Place

Michigan Avenue 200 m from Wintrust Arena

# 36 in Hotels In Chicago With Rooftop Pool

8.5 /10

(292 reviews)

Surrounded by attractions like Glessner House Museum, Arie Crown Theater, and many more, Home2 Suites By Hilton Chicago McCormick Place provides an excellent location for its guests to explore in the (Read More)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 8 room options

$ 86 onwards

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37. Four Seasons Chicago

Four Seasons Chicago

Michigan Avenue 100 m from Fourth Presbyterian Church

# 37 in Hotels In Chicago With Rooftop Pool

9.0 /10

(153 reviews)

With French décor and classy furnishing, Four Seasons Chicago offers with spacious and luxurious accommodations equipped with comfortable beds, French windows and a number of necessary and mode (Read More)rn 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 18 room options

$ 370 onwards

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38. Hilton Garden Inn Chicago McCormick Place

Hilton Garden Inn Chicago McCormick Place

Michigan Avenue 200 m from Wintrust Arena

# 38 in Hotels In Chicago With Rooftop Pool

8.1 /10

(303 reviews)

If you are visiting Chicago this vacation and looking for a property that will provide you with luxury at its best then you are in luck. Hilton Garden Inn Chicago McCormick Place has got the best of a (Read More)menities 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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39. 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

# 39 in Hotels In Chicago With Rooftop Pool

7.3 /10

(548 reviews)

Dive into the outdoor swimming pool, or relax on the sun loungers surrounding it, or enjoy a guilt free delicious meal at the on- site dining options after hitting the gym for the daily fitness regime (Read More), 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

$ 111 onwards

View Deal >

40. Holiday Inn Chicago Mart Plaza River North

Holiday Inn Chicago Mart Plaza River North

# 40 in Hotels In Chicago With Rooftop Pool

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. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

The Loop 100 m from University Club of Chicago

8.7

(933 reviews)

Facilities: Parking , Bar , Wifi

The Silversmith Hotel Chicago Downtown is a historic hotel located in the heart of Chicago. It offers comfortable and spacious rooms, impeccable cleanliness, and friendly and welcoming staff. The hote (Read More)l 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

$149 onwards

View Deal >

2. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

The Loop 500 m from Chicago Riverwalk

8.0

(959 reviews)

Facilities: Parking , Bar , Wifi , Food

4 star hotel with 35 room options

$111 onwards

View Deal >

3. The Palmer House Hilton

The Palmer House Hilton

The Loop 100 m from Adams/Wabash Station

7.4

(847 reviews)

Facilities: Parking , Bar , Wifi , Pool , Food

4 star hotel with 17 room options

$121 onwards

View Deal >

4. The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

Michigan Avenue 300 m from House of Blues Chicago

8.4

(878 reviews)

Facilities: Parking , Bar , Wifi , Pool

4 star hotel with 16 room options

$128 onwards

View Deal >

5. Hotel Chicago Downtown, Autograph Collection

Hotel Chicago Downtown, Autograph Collection

The Loop 0 m from House of Blues Chicago

8.6

(853 reviews)

Facilities: Parking , Bar , Wifi

4 star hotel with 4 room options

$93 onwards

View Deal >

6. Swissotel Chicago

Swissotel Chicago

The Loop 500 m from Millennium Park

8.4

(857 reviews)

Facilities: Parking , Bar , Wifi , Food

4 star hotel with 30 room options

$111 onwards

View Deal >

7. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District

The Loop 300 m from Adams/Wabash Station

8.6

(820 reviews)

Facilities: Parking , Wifi , Food

Located in the heart of Chicago, the Hampton Inn Majestic Chicago Theatre District offers a range of amenities, including parking, a fitness center, a business center, and free WiFi. The hotel is hous (Read More)ed 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

$94 onwards

View Deal >

8. Crowne Plaza - Chicago West Loop, an IHG Hotel

Crowne Plaza - Chicago West Loop, an IHG Hotel

The Loop 800 m from wndr museum

7.9

(935 reviews)

Facilities: Parking , Bar , Wifi , Food

Hotel with 11 room options

$126 onwards

View Deal >

9. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

The Loop 300 m from The Chicago Theatre

8.7

(1239 reviews)

Facilities: Parking , Bar , Wifi

Staypineapple, An Iconic Hotel located in The Loop, Chicago, offers a unique and enjoyable experience with its old-style charm and modern amenities. The hotel's customer service is top-notch, with fri (Read More)endly 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

$71 onwards

View Deal >

10. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

The Loop 100 m from Chicago Riverwalk

7.9

(1143 reviews)

Facilities: Parking , Bar , Wifi , Food

The Hampton Inn Chicago Downtown/N Loop/Michigan Ave is a modest yet comfortable hotel located in the heart of downtown Chicago. With its convenient location, guests have easy access to top attraction (Read More)s such as Millennium Park. The hotel provides a range of amenities, including parking, a fitness center, a business center, and free WiFi. The staff at the hotel is highly praised for their helpfulness and courtesy, going above and beyond to ensure a pleasant stay. Overall, the Hampton Inn offers a wonderful experience for guests visiting Chicago.

Hotel with 9 room options

$84 onwards

View Deal >

11. Arlo Chicago

Arlo Chicago

Michigan Avenue 200 m from The Chicago Theatre

8.4

(1247 reviews)

Facilities: Bar , Wifi

4 star hotel with 7 room options

$83 onwards

View Deal >

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Hotels Near Museum of Science and Industry

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Hotels Near Hilton Chicago

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Hotels Near Wicker Park

Best Pet Friendly Hotels In Chicago

Best Beach Hotels in Chicago

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Places to visit in Chicago

Navy Pier Art Institute of Chicago

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FAQs on Best Hotels In Chicago With Rooftop Pool for a Luxury Trip

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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