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Woodlawn Hotels, Chicago

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18 Nov - 19 Nov
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19 Nov - 20 Nov
This weekend
21 Nov - 23 Nov
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28 Nov - 30 Nov

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4545 Cheap Hotels in Woodlawn - Specials, Reviews, & Last Minute Deals

Hallway
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 NZ$130
includes taxes & fees
18 Dec - 19 Dec
Best Motel By OYO Chicago I-90
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 13.1 km from Woodlawn
8.8 out of 10, Excellent, (3109)
"Excellent stay, close to everything and the staff was super nice "
United States
Kieata
The price is NZ$216
includes taxes & fees
16 Dec - 17 Dec
Eurostars Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4814)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is NZ$184
includes taxes & fees
19 Nov - 20 Nov
River Hotel
Terrace/patio
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, (2145)
"Great stay "
United States
Melinda
The price is NZ$202
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Terrace/patio
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (4042)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is NZ$219
includes taxes & fees
19 Nov - 20 Nov
citizenM Chicago Downtown
Terrace/patio
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, (2236)
"Room was spotless…staff was great!"
United States
Tamika
The price is NZ$250
includes taxes & fees
16 Dec - 17 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2912)
"Great location!!"
United States
sarah e
The price is NZ$195
includes taxes & fees
23 Nov - 24 Nov
Aloft Chicago Mag Mile
Ballroom
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, (3324)
"Great stay!"
United States
Rose
The price is NZ$202
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 10.7 km from Woodlawn
8.4 out of 10, Very good, (2312)
"Clean Rooms & very nice staff"
United States
Teresa
The price is NZ$272
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
Bar (on property)
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, (4176)
"Great location. "
United States
Rodger
The price is NZ$157
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2579)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is NZ$167
includes taxes & fees
20 Nov - 21 Nov
Freehand Chicago
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 13.1 km from Woodlawn
8.4 out of 10, Very good, (327)
"very clean and modern, staff was very friendly"
United States
Edrick
The price is NZ$140
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (9595)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
Congress Plaza Hotel
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1691)
"very nice staff & very clean hotel "
United States
Amy
The price is NZ$187
includes taxes & fees
23 Nov - 24 Nov
Crowne Plaza Chicago West Loop by IHG
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (2811)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is NZ$263
includes taxes & fees
15 Dec - 16 Dec
Hotel Riu Plaza Chicago
Rooftop terrace
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.0 out of 10, Wonderful, (2239)
"Clean room, friendly staff, convenient location. "
United States
Arthera
The price is NZ$309
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric The Loop Chicago
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (2080)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown
Restaurant
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 star property
The Loop, 10.4 km from Woodlawn
8.2 out of 10, Very good, (2624)
"Loved our stay here! Was easy to check in and staff was super friendly! Loved the area and the walk to millennium park was nice."
United States
Mary
The price is NZ$167
includes taxes & fees
15 Dec - 16 Dec
Best Western Grant Park Hotel
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 11.7 km from Woodlawn
8.4 out of 10, Very good, (2069)
"Great place to stay."
United States
Aaron
The price is NZ$264
includes taxes & fees
24 Nov - 25 Nov
Palmer House a Hilton Hotel
Lobby
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3410)
"Great stay"
United States
Jenine
The price is NZ$278
includes taxes & fees
7 Dec - 8 Dec
LondonHouse Chicago, Curio Collection by Hilton
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.
View all properties

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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

The Loop - Downtown which includes a river or creek

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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 a city and modern architecture

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Woodlawn Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt"
Scott 2-night trip
Posted 6 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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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.