Find a Hotel in Woodlawn

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top hotels in Woodlawn

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $242 total per night from Jul 5 to Jul 6
$242 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant ...
"Beautiful hotel, perfect location! Loved everything about this hotel. Breakfast was great. But they really want you out of the restaurant right at the closing time so give yourself time in the morning for breakfast"

Reviewed on Jun 21, 2026

Opens in a new windowHotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express ...
"Cleaneage rooms. Great location. Lovely staff"

Reviewed on Jun 21, 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
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
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
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 ...
"Amazing hotel! We will be back"

Reviewed on Jun 22, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $248 total per night from Jun 30 to Jul 1
$248 total
Jun 30 - Jul 1
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 business center, express ...
"Prepaid parking through Expedia not honored at the hotel. Staff completely unhelpful in sorting this issue out. Forced to double pay for parking. Rooms dated with older furnishings. Beds old. Plumbing drained poorly. Location nice but otherwise I would not recommend."

Reviewed on Jun 22, 2026

Opens in a new windowPalmer House a Hilton Hotel
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
$154 nightly
The price is $183 total per night from Jun 29 to Jun 30
$183 total
Jun 29 - Jun 30
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, ...
"There are so many things to like about the Ambassador Hotel, starting with its incredible Gold Coast location, it’s amazing history as a landmark hotel in Chicago, it’s traditional, elegant interiors nicely updated. Last but not least a big shout out to the front desk as well as restaurant/cocktail ..."

Reviewed on Jun 22, 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
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
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 ...
"It was very hot. Leaving the hotel room was a great reprieve as it was much cooler outside. I called the front desk to see if there was a way to make the AC stronger, but they answered and hung up immediately the first 4 times I called. I tried again the next day and they told me there was a shared ..."

Reviewed on Jun 22, 2026

Opens in a new windowCongress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $170 total per night from Jul 5 to Jul 6
$170 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also ...
"Easy check in, clean room, helpful staff, great location."

Reviewed on Jun 22, 2026

Opens in a new windowFreehand Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
$131 nightly
The price is $155 total per night from Jun 29 to Jun 30
$155 total
Jun 29 - Jun 30
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Business travelers can take advantage of the free WiFi ...
"The hotel was in a great location, and the staff were friendly and welcoming. My only complaint was that the hallway smelled like cigarettes and damp carpet. Overall, it was a pleasant stay, but the hallway and elevator odor could definitely be improved."

Reviewed on Jun 21, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $146 total per night from Jul 5 to Jul 6
$146 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
"Basic but a great location"

Reviewed on Jun 22, 2026

Opens in a new windowTravelodge by Wyndham Downtown Chicago
Don't see what you're looking for?
See all available properties in Woodlawn
View all properties
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Amazing hotel! We will be back"
A verified traveler stayed at Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago

Explore More Ways to Travel with Travelocity