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Aug 14 - Aug 16
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Top hotels in Woodlawn

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
$211 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
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, ...
"Great stay"

Reviewed on Aug 12, 2026

Opens in a new windowHyatt Regency McCormick Place Chicago
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$251 nightly
The price is $298 total per night from Aug 16 to Aug 17
$298 total
Aug 16 - Aug 17
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, ...
"great location, nice sized room"

Reviewed on Aug 11, 2026

Opens in a new windowOmni Chicago Hotel
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
$206 nightly
The price is $245 total per night from Sep 10 to Sep 11
$245 total
Sep 10 - Sep 11
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. ...
"Overall, I’d give my stay about a 3.8/5. There were some good things, but also quite a few areas that could use improvement. The room was really small, and the bathroom felt like it was in a closet — very cramped. The furniture and everything in the room also felt pretty old and worn. The closet ..."

Reviewed on Aug 11, 2026

Opens in a new windowThe Allegro Royal Sonesta Hotel Chicago Loop
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $230 total per night from Sep 7 to Sep 8
$230 total
Sep 7 - Sep 8
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, ...
"A+ super impressed honestly. Will be back again!"

Reviewed on Aug 12, 2026

Opens in a new windowHilton Chicago
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
$130 total
Sep 8 - Sep 9
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
"Lower price$"

Reviewed on Aug 11, 2026

Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $170 total per night from Aug 31 to Sep 1
$170 total
Aug 31 - Sep 1
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 8 conference ...
"Me encanto"

Reviewed on Aug 12, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
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 30 to Aug 31
$170 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 free WiFi in public areas, express check-out, ...
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
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 ...
Opens in a new windowHyatt Regency O'Hare Chicago
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
$289 nightly
The price is $344 total per night from Sep 2 to Sep 3
$344 total
Sep 2 - Sep 3
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 ...
Opens in a new windowFairmont Chicago at Millennium Park
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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

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Me encanto"
A verified traveler stayed at The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

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