Explore top 2026 4 Star Hotels in Woodlawn

Name: Hyatt Regency Chicago
Price range: $329 total
Rating: 9.4

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Top Woodlawn 4 Star hotels

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$161 nightly

$191 total

Oct 25 - Oct 26

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. ...

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, ...

8/10 Very Good! (2,430 reviews)

"beautful. clean"

Reviewed on Oct 6, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

Fully refundableReserve now, pay when you stay

$183 nightly

$218 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...

Hilton Chicago

720 S Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

$193 nightly

$227 total

Oct 30 - Oct 31

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...

8.6/10 Excellent! (3,377 reviews)

"A bit on the older end but in very good shape despite it's age. Huge hotel, very fast elevators which is a big bonus. No waiting. Great location and awesome for a Bears game."

Reviewed on Oct 6, 2026

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

$151 nightly

$179 total

Nov 1 - Nov 2

Total with taxes and fees

This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi ...

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave Chicago IL

Fully refundable

$241 nightly

$287 total

Oct 31 - Nov 1

Total with taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the sauna and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee ...

9.2/10 Wonderful! (3,366 reviews)

"Fan of Michael Jordan, but it is not a good restaurant. Poor quality of food and bad service"

Reviewed on Oct 6, 2026

L7 Chicago by LOTTE

225 N Wabash Ave Chicago IL

Fully refundableReserve now, pay when you stay

$216 nightly

$257 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a lobby fireplace are also ...

9.6/10 Exceptional! (4,973 reviews)

"Excellent good size rooms. Location is central and almost all attractions are at walking distance."

Reviewed on Oct 6, 2026

The Wade

644 N Lake Shore Dr Chicago IL

Fully refundableReserve now, pay when you stay

$142 nightly

$169 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

$161 nightly

$183 total

Oct 23 - Oct 24

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...

9/10 Wonderful! (3,242 reviews)

"Clean facility, easy to navigate, comfortable beds, what more could you ask for!!"

Reviewed on Oct 6, 2026

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

Fully refundableReserve now, pay when you stay

$277 nightly

$329 total

Oct 31 - Nov 1

Total with taxes and fees

This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, ...

9.4/10 Exceptional! (3,498 reviews)

"Better organize breakfast hours: often we had long line in buffet and waiting time ~10-15min. For morning hours - it's unacceptable"

Reviewed on Oct 6, 2026

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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.