Explore top 2025 5 Star Hotels in Woodlawn

Name: Art Villa
Price range: $1,031 total
Rating: 10

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Top Woodlawn 5 Star hotels

The Langham, Chicago

330 North Wabash Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

$505 nightly

$592 total

Dec 5 - Dec 6

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, ...

9.6/10 Exceptional! (1,018 reviews)

Remarkable stay! I will return for my next stay in downtown Chicago. Have stayed at other 5 Star Hotels but this one is now my #1 choice. Thank you to all the staff that made my family's stay a memorable one.

Reviewed on Oct 28, 2025

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago, IL

Fully refundableReserve now, pay when you stay

$431 nightly

$506 total

Nov 16 - Nov 17

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 ...

9.4/10 Exceptional! (1,762 reviews)

The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. ...

Reviewed on Nov 3, 2025

Four Seasons Hotel Chicago

120 East Delaware Place, Chicago, IL

Fully refundableReserve now, pay when you stay

$490 nightly

$575 total

Nov 24 - Nov 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 24-hour business ...

9.4/10 Exceptional! (998 reviews)

Wonderful

Reviewed on Oct 28, 2025

The Peninsula Chicago

108 East Superior Street, Chicago, IL

Fully refundableReserve now, pay when you stay

$575 nightly

$675 total

Nov 16 - Nov 17

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. ...

9.6/10 Exceptional! (1,025 reviews)

Amazing rooms, walkable to shopping and restaurants. Great rooftop bar

Reviewed on Oct 24, 2025

Waldorf Astoria Chicago

11 E. Walton Street, Chicago, IL

Fully refundableReserve now, pay when you stay

$489 nightly

$574 total

Nov 23 - Nov 24

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 ...

9.2/10 Wonderful! (1,001 reviews)

Beautiful place and service

Reviewed on Oct 29, 2025

Nobu Hotel Chicago

155 N. Peoria Street, Chicago, IL

Fully refundableReserve now, pay when you stay

$327 nightly

$384 total

Nov 23 - Nov 24

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 ...

9.2/10 Wonderful! (742 reviews)

yes

Reviewed on Oct 30, 2025

Park Hyatt Chicago

800 N Michigan Ave, Chicago, IL

Fully refundableReserve now, pay when you stay

$495 nightly

$581 total

Nov 23 - Nov 24

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, ...

9.4/10 Exceptional! (999 reviews)

This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. ...

Reviewed on Oct 20, 2025

The Ritz-Carlton, Chicago

160 E Pearson Street, Chicago, IL

Fully refundableReserve now, pay when you stay

$444 nightly

$521 total

Nov 9 - Nov 10

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, ...

9/10 Wonderful! (1,000 reviews)

Great location

Reviewed on Oct 14, 2025

The St. Regis Chicago

401 East Upper Wacker Drive, Chicago, IL

Fully refundableReserve now, pay when you stay

$464 nightly

$545 total

Nov 24 - Nov 25

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 ...

9/10 Wonderful! (77 reviews)

Clean room, amazing view

Reviewed on Sep 7, 2025

Art Villa

467 N Armour St, Chicago, IL

$823 nightly

$1,031 total

Nov 6 - Nov 7

Total with taxes and fees

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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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent Woodlawn hotel reviews by fellow wanderers

Aloft Chicago Mag Mile

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"Male staff members were nice and helpful. The full bar was great. The interior was stylish, and I loved the fireplace with its cozy atmosphere. I stayed here for 1 week."

A verified traveler stayed at Aloft Chicago Mag Mile