Explore top 2026 5 Star Hotels in Woodlawn

Name: Art Villa
Rating: 10

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Top Woodlawn 5 Star hotels

Four Seasons Hotel Chicago

120 East Delaware Place Chicago IL

Fully refundableReserve now, pay when you stay

$420 nightly

$493 total

Jan 11 - Jan 12

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 ...

9.2/10 Wonderful! (998 reviews)

Staff, amenities, special touches for kids

Reviewed on Dec 29, 2025

The Langham, Chicago

330 North Wabash Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$413 nightly

$485 total

Feb 1 - Feb 2

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! (1,007 reviews)

Yes didn’t know you get free breakfast

Reviewed on Jan 4, 2026

The Peninsula Chicago

108 East Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$475 nightly

$558 total

Jan 25 - Jan 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. ...

9.6/10 Exceptional! (1,017 reviews)

Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.

Reviewed on Dec 29, 2025

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$319 nightly

$374 total

Jan 11 - Jan 12

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! (1,814 reviews)

Perfection

Reviewed on Jan 3, 2026

Waldorf Astoria Chicago

11 E. Walton Street Chicago IL

Fully refundableReserve now, pay when you stay

$380 nightly

$446 total

Feb 1 - Feb 2

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! (1,000 reviews)

Amazing

Reviewed on Dec 29, 2025

Park Hyatt Chicago

800 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$387 nightly

$454 total

Jan 7 - Jan 8

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)

Great

Reviewed on Dec 17, 2025

Nobu Hotel Chicago

155 N. Peoria Street Chicago IL

Fully refundableReserve now, pay when you stay

$310 nightly

$364 total

Jan 11 - Jan 12

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! (769 reviews)

Staff were excellent, room was large and spotless. Would definitely return to Nobu Chicago

Reviewed on Dec 29, 2025

The Ritz-Carlton, Chicago

160 E Pearson Street Chicago IL

Fully refundableReserve now, pay when you stay

$386 nightly

$453 total

Feb 5 - Feb 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 business center, ...

9/10 Wonderful! (1,001 reviews)

great location

Reviewed on Dec 29, 2025

The St. Regis Chicago

401 East Upper Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$446 nightly

$524 total

Feb 1 - Feb 2

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! (86 reviews)

All the anove

Reviewed on Dec 15, 2025

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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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.