Explore top 2026 5 Star Hotels in Jackson Park Highlands

Name: Art Villa
Rating: 10

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Top Jackson Park Highlands 5 Star hotels

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$510 nightly

$606 total

May 25 - May 26

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business ...

9.4/10 Exceptional! (1,002 reviews)

"Este hotel están bastante bien situado cerca de tiendas sobre todo Bloomingdale que están en el mismo edificio es una buena opción"

Reviewed on May 18, 2026

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$592 nightly

$703 total

Jun 11 - Jun 12

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...

9.8/10 Exceptional! (1,007 reviews)

"Thumbs up"

Reviewed on May 18, 2026

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$446 nightly

$531 total

May 25 - May 26

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly ...

9.6/10 Exceptional! (1,875 reviews)

"Great experience! Would stay here agin"

Reviewed on May 18, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$575 nightly

$684 total

May 25 - May 26

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and babysitting. ...

9.8/10 Exceptional! (1,005 reviews)

"Great stay!"

Reviewed on May 17, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$514 nightly

$611 total

May 25 - May 26

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi ...

9.4/10 Exceptional! (1,001 reviews)

"Wonderful Hotel will definitely be looking forward to going back."

Reviewed on Apr 25, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$484 nightly

$575 total

May 24 - May 25

Total with taxes and fees

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, ...

9.2/10 Wonderful! (1,004 reviews)

"The property was ok, not a level of a real Ritz Carlton"

Reviewed on May 19, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$545 nightly

$648 total

May 25 - May 26

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, ...

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$343 nightly

$408 total

May 25 - May 26

Total with taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. There's a bar/lounge on site, and a 24-hour ...

9.4/10 Exceptional! (848 reviews)

"For $900 a night, the bathroom should at least very clean and not covered in mold and mildew"

Reviewed on May 18, 2026

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$595 nightly

$707 total

May 25 - May 26

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...

Art Villa

467 N Armour St Chicago IL

A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. ...

10/10 Exceptional! (2 reviews)

Reviewed on Aug 12, 2025

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Recent Jackson Park Highlands hotel reviews by fellow wanderers

Congress Plaza Hotel

3 out of 5

Posted 1 hour ago

Travelocity Verified Review

"A old, classic hotel and a low room rate, I was not expecting 'up to date modern'. Plusses: Room was large and clean, no noise from other guests, bag storage free, price compared to other hotels very low. Minuses: Unable to turn heater on _only a thin quilt blanket for bed, noise from toilet filling continously - sometimes had to wait an hour to flush again, hot water from shower took long time to come through. Being alone and not too fussy I was ok with this for the week. Built in 20s ? once must have been quite glamorous but investment needed to renovate a bit."

A verified traveler stayed at Congress Plaza Hotel

The Chicago Hotel Collection - Magnificent Mile

1 out of 5

Posted 6 hours ago

Travelocity Verified Review

"BEWARE: I booked and paid for this hotel a month in advance. My train was delayed a few hours, so I arrived at the hotel about 7pm. However, I completed an echeck-in at the hotels request at 1pm. Upon arriving, there was a short line of people waiting to check-in and they were upset and asking to speak with a manager. When I got to the counter with my 2 kids, I was told they sold my room and there wasn't anything available for us. And on top of that, the money I had paid for the 2 nights stay was not refunded yet. I had only taken a some money with me for our daily activities so I had to use our daily living money to pay for another room that was a 30 min drive outside of the city. Completely ruined the trip I had planned for my daughter's birthday. The young girls running the front desk showed no remorse at all for leaving us with no place to stay. Their reasoning was that the hotel had sold out by 2:30 even though check in wasn't until 4. I had to call Expedia to get my refund and the hotel told Expedia that they were experiencing some technical errors with their booking system. A complete lie. So beware if this hotel. A reservation and prepaid room mean nothing. They will leave you on the streets of Chicago without blinking their eyes. Shameful . They sent me a text, while I was sitting in their lobby trying to figure out where I could stay on the money I had left ."

A verified traveler stayed at The Chicago Hotel Collection - Magnificent Mile

Holiday Inn Chicago Dwtn - The Mart by IHG

1 out of 5

Posted 7 hours ago

Travelocity Verified Review

"terrible rooms, terrible cleaning non stop spiders coming from the windows, water damage in bathroom and main room restaurant staff was rude and accused us of stealing breakfast but the assistant manager was very understanding"

A verified traveler stayed at Holiday Inn Chicago Dwtn - The Mart by IHG

Freehand Chicago

1 out of 5

Posted 12 hours ago

Travelocity Verified Review

"I booked a single room, king size bed for my sister and they tried giving her a shared quad, twin bed. We canceled immediately but still have not receive a refund. Ive called and left a message, no reply. 2nd time I called, I was placed on hold till the call dropped."

A verified traveler stayed at Freehand Chicago