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Aug 21 - Aug 23
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Top hotels in Woodlawn

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. A convenience store and luggage storage are also ...
"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"

Reviewed on Aug 21, 2026

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Opens in a new windowKasa Magnificent Mile Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Aug 30 to Aug 31
$193 total
Aug 30 - Aug 31
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 ...
"Excellent"

Reviewed on Aug 21, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $145 total per night from Aug 23 to Aug 24
$145 total
Aug 23 - Aug 24
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. ...
"Our stay at the River Hotel was fantastic! Check-in was easy and fast, the staff was friendly and welcoming, and the location was perfect. It’s within walking distance of so many great places, which made exploring the area incredibly convenient. Overall, we had a wonderful stay and would definitely ..."

Reviewed on Aug 21, 2026

Opens in a new windowRiver Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $351 total per night from Aug 23 to Aug 24
$351 total
Aug 23 - Aug 24
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room ...
"I’ve stayed at this hotel brand at several locations, and unfortunately, this property was by far the worst. The room did not meet the expected standards to the point that I had to check out and did not stay. Extremely disappointing."

Reviewed on Aug 21, 2026

Opens in a new windowFairmont Chicago at Millennium Park
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $170 total per night from Aug 24 to Aug 25
$170 total
Aug 24 - Aug 25
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, ...
"Incredible Gold Coast location and the bar staff was great. The room however was really bad, run down, broken furniture, holes in sheets. Shocked honestly. In speaking with other guests on elevator/ my experience was similar to theirs. Really unfortunate. I let staff know - zero follow up or care. ..."

Reviewed on Aug 21, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $130 total per night from Sep 8 to Sep 9
$130 total
Sep 8 - Sep 9
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
Opens in a new windowCongress Plaza Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $261 total per night from Sep 7 to Sep 8
$261 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, ...
Opens in a new windowHyatt Regency McCormick Place Chicago
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
$222 nightly
The price is $264 total per night from Aug 30 to Aug 31
$264 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. ...
Opens in a new windowThe Allegro Royal Sonesta Hotel Chicago Loop
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$276 nightly
The price is $328 total per night from Sep 7 to Sep 8
$328 total
Sep 7 - Sep 8
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, ...
Opens in a new windowHyatt Regency Chicago
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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.

Woodlawn Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Woodlawn area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Woodlawn to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Woodlawn are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Woodlawn hotel reviews by fellow wanderers

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Loved being right on MagMile! Great dining options within walking distance. Cool funky vibe."
A verified traveler stayed at The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

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