Explore top 2026 5 Star Hotels in Woodlawn

Name: Art Villa
Rating: 10

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Top Woodlawn 5 Star hotels

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$469 nightly

$557 total

Jun 21 - Jun 22

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! (1,884 reviews)

"We love the pool, cleanliness in the room .Friendly staff"

Reviewed on Jun 6, 2026

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$513 nightly

$610 total

Jun 28 - Jun 29

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! (1,004 reviews)

"Ask for a water view!"

Reviewed on May 31, 2026

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$525 nightly

$624 total

Jul 5 - Jul 6

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! (1,003 reviews)

"We had a lovely 2 night stay in Chicago and the room with lake view was superb with lovely touches by the cleaning staff who made the stay very special"

Reviewed on Jun 1, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$602 nightly

$716 total

Jul 5 - Jul 6

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! (1,006 reviews)

"Excellent and fast service, walking distance to restaurants, shopping, lake, etc."

Reviewed on Jun 7, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

$513 nightly

$609 total

Jul 5 - Jul 6

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! (1,004 reviews)

"Fabulous"

Reviewed on Jun 7, 2026

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$446 nightly

$531 total

Jun 28 - Jun 29

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! (1,001 reviews)

"best service. nicest people. great room. excellent restaurants. its the Ritz and lived up to its reputation."

Reviewed on May 26, 2026

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$498 nightly

$592 total

Jun 28 - Jun 29

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, ...

9.6/10 Exceptional! (1,002 reviews)

"This is a very good hotel. It is in a great location and it does everything so well."

Reviewed on Jun 8, 2026

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$356 nightly

$423 total

Jun 28 - Jun 29

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! (863 reviews)

"The staff was very helpful and courteous. I wish the hotel had more amenities, such as massage services."

Reviewed on May 29, 2026

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$644 nightly

$766 total

Jul 5 - Jul 6

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 ...

9.2/10 Wonderful! (120 reviews)

"👌"

Reviewed on Jun 7, 2026

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 Woodlawn hotel reviews by fellow wanderers

Congress Plaza Hotel

4 out of 5

Posted less than an hour ago

Travelocity Verified Review

"Just didn’t feel nice enough for the price"

A verified traveler stayed at Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites

2 out of 5

Posted 1 hour ago

Travelocity Verified Review

"The hotel staff were friendly, and the rooms were mostly clean; however, the hotel itself is very dated. The tile in the shower is discolored, the sofa bed is extremely thin and miserable to sleep on, and the mattresses are subpar at best. Not to mention the microwave had a broken foot on it which made it tilt causing our food to be heated unevenly, and the refrigerator (despite us adjusting the temperature) kept our drinks, just slightly cooler than room temperature. The walls between rooms are also incredibly thin. Hilton definitely needs to spend some money on upkeep. I know we won’t be back until they do."

A verified traveler stayed at Hilton Chicago/Magnificent Mile Suites

The Chicago Hotel Collection - Magnificent Mile

5 out of 5

Posted 2 hours ago

Travelocity Verified Review

"The property was good, no pool which is fine for us. Read that there was a hidden mandatory fee but book with Expedia and that was not the case. Card didn’t open the door to the hotel room on 2 occasions but that was the only hiccup"

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

Hotel Felix River North/Magnificent Mile

4 out of 5

Posted 4 hours ago

Travelocity Verified Review

"Staff was friendly and hotel was very clean! It’s in a great location and we enjoyed our room a lot! I took off a point because when we asked for fresh towels, they never came to our room and we had to ask again. But overall very comfortable and pleasant stay!"

A verified traveler stayed at Hotel Felix River North/Magnificent Mile