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Woodlawn Hotels, Chicago

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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Our top choices for Woodlawn hotels

Room, 1 King Bed, Non Smoking
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.4 out of 10, (48)
"Clean room "
United States
Pierre
The price is AU$110
includes taxes & fees
13 Jan - 14 Jan 2026
Best Motel By OYO Chicago I-90
Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2651)
"It's an excellent place."
United States
Jose
The price is AU$116
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand Chicago
Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2953)
"The room was very clean, the location was excellent."
United States
Craig
The price is AU$140
includes taxes & fees
14 Jan - 15 Jan 2026
Aloft Chicago Mag Mile
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (1996)
"A good place for stay "
United States
Julio
The price is AU$139
includes taxes & fees
18 Jan - 19 Jan 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 12.7 km from Woodlawn
8.4 out of 10, Very good, (2752)
"Excellent place to stay "
United States
Teniesha
The price is AU$192
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Magnificent Mile, 13.1 km from Woodlawn
8.4 out of 10, Very good, (2999)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is AU$155
includes taxes & fees
12 Jan - 13 Jan 2026
Warwick Allerton - Chicago
Lobby
Congress Plaza Hotel

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (9674)
"Wonderful stay!"
United States
Zach
The price is AU$167
includes taxes & fees
2 Jan - 3 Jan 2026
Congress Plaza Hotel
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2191)
"Very friendly staff, clean rooms, the location is amazing and near of everything "
United States
Sarwat
The price is AU$159
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
9.0 out of 10, Wonderful, (1053)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is AU$218
includes taxes & fees
2 Jan - 3 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 12.8 km from Woodlawn
8.4 out of 10, Very good, (4254)
"Excellent location Restaurant attached "
United States
Rebecca
The price is AU$153
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Nightclub
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.8 out of 10, Excellent, (3320)
"Great hotel "
United States
Anthony
The price is AU$145
includes taxes & fees
1 Jan - 2 Jan 2026
Club Quarters Hotel, Central Loop, Chicago
Property amenity
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.4 out of 10, Very good, (1525)
"Great staff and great location. "
United States
Joe
The price is AU$179
includes taxes & fees
4 Jan - 5 Jan 2026
The Wade
Bar (on property)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.6 km from Woodlawn
8.2 out of 10, Very good, (3786)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is AU$136
includes taxes & fees
21 Dec - 22 Dec
The Whitehall Hotel, BW Premier Collection
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4837)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is AU$137
includes taxes & fees
19 Jan - 20 Jan 2026
River Hotel
Exterior
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
River North, 12.7 km from Woodlawn
8.8 out of 10, Excellent, (3487)
"Very helpful staff, clean rooms and really great breakfast buffet. "
United States
Katherine
The price is AU$192
includes taxes & fees
21 Dec - 22 Dec
voco Chicago Downtown - Riverwalk by IHG
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (4125)
"Great stay"
United States
Ericka
The price is AU$165
includes taxes & fees
24 Dec - 25 Dec
citizenM Chicago Downtown
View from room
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (3497)
"Great place to stay "
United States
RaShawna
The price is AU$159
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Chicago/Magnificent Mile Suites
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3412)
"The Hotel was amazing great location "
United States
Donnisha
The price is AU$291
includes taxes & fees
5 Jan - 6 Jan 2026
Hyatt Regency Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 12.6 km from Woodlawn
9.4 out of 10, Exceptional, (2268)
"Great staff and restaurants!!"
United States
Abigale
The price is AU$213
includes taxes & fees
15 Jan - 16 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby sitting area
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13 km from Woodlawn
8.4 out of 10, Very good, (1789)
"Great stay in a great area."
United States
Giselle
The price is AU$109
includes taxes & fees
21 Dec - 22 Dec
Hotel Saint Clair- Magnificent Mile
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.
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Our guide on where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most.
Downtown Chicago featuring a city

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Magnificent Mile - River North

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop - Downtown which includes a river or creek

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Chicago showing rides

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top Woodlawn Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean Room"
Zaire 2-night trip
Posted 1 day ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

What's it like in Woodlawn?
Woodlawn is a neighbourhood that travellers like for its beaches, restaurants and gardens. Looking for sights you might find in a travel guide about Woodlawn? Consider a visit to Lake Michigan while you're in the neighbourhood.
Where is the best place to stay in Woodlawn?
Based on Expedia customer reviews, Best Motel By OYO Chicago I-90 is the highest ranked property in Woodlawn. This property offers free valet parking and flat-screen TVs.
How many hotels are there in the Woodlawn area?
If you're searching for places to stay in Chicago, Expedia has something to meet your needs with 46 Woodlawn hotels and other accommodation options to choose from.
If I need to cancel my hotel reservation in Woodlawn, will I receive a refund?
Yes, the majority of hotel room reservations are refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Enter dates in and click on "Search", then filter by "fully refundable" to view the best deals available in Woodlawn.
What can I see and do in this Chicago neighbourhood?
Spend some time exploring the great outdoors at Lake Michigan, Jackson Park and Bob-O-Link Meadow. Lorado Taft's Midway Studios and Jackson Park Driving Range are also a couple of places to visit in the neighbourhood. Oak Woods Cemetery, Stony Island Arts Bank and Rockefeller Memorial Chapel are just a few of the places to visit in and around Woodlawn. While you're out sightseeing in Chicago, make sure that you visit other sights such as Oriental Institute Museum or Bond Chapel.
How can I get around Woodlawn and the greater Chicago area?
Looking for a quick way to explore more of the city? Catch a ride on metro transit at Cottage Grove Station and King Drive Station. To venture out of town, take a train from Chicago 63rd Street Station.

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