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9 Dec - 10 Dec
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19 Dec - 21 Dec

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Our top choices for Woodlawn hotels

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 1.476.272 ₫
1.917.529 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
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
9.0 out of 10, Wonderful, (3154)
"Amazing and will be staying again!"
United States
Angie
The price is 2.467.577 ₫
2.896.687 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Eurostars Magnificent Mile
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, (2184)
"Nice Hotel"
United States
Alan
The price is 2.356.236 ₫
2.765.986 ₫ total
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (4852)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is 2.151.139 ₫
2.525.221 ₫ total
includes taxes & fees
22 Dec - 23 Dec
River Hotel
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, (3457)
"Great place to stay "
United States
RaShawna
The price is 2.788.572 ₫
3.273.505 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hilton Chicago/Magnificent Mile Suites
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, (2263)
"Smooth check in and beautiful hotel"
United States
Monique
The price is 2.521.357 ₫
3.857.481 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
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, (2956)
"Great location and great staff!!"
United States
lynne
The price is 2.188.046 ₫
2.568.546 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Aloft Chicago Mag Mile
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (4101)
"Great stay"
United States
Ericka
The price is 2.820.734 ₫
3.311.260 ₫ total
includes taxes & fees
14 Dec - 15 Dec
citizenM Chicago Downtown
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 10.7 km from Woodlawn
8.4 out of 10, Very good, (2366)
"We had a great stay and will be back again."
United States
Amber
The price is 3.004.741 ₫
4.300.989 ₫ total
includes taxes & fees
21 Dec - 22 Dec
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, (4237)
"Staff were amazing."
United States
Debra
The price is 2.161.766 ₫
2.537.697 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 11.3 km from Woodlawn
8.4 out of 10, Very good, (1009)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is 2.662.562 ₫
3.441.925 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
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, (2117)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
Silversmith Hotel Chicago Downtown
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, (366)
"Good place, good location, friendly staff and a great bar! "
United States
Georgi
The price is 1.555.226 ₫
1.825.678 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
FOUND Hotel Chicago River North
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, (1751)
"The location was great!!"
United States
Yvette
The price is 2.253.951 ₫
2.645.912 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Crowne Plaza Chicago West Loop by IHG
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2633)
"The room was spotless and the staff where great!"
United States
Maria
The price is 1.622.906 ₫
2.369.341 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Freehand Chicago
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, (9649)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is 3.608.831 ₫
4.236.408 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Congress Plaza Hotel
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, (2948)
"Excellent stay great location and great rooms"
United States
Joseph
The price is 2.477.422 ₫
3.651.127 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Hotel Riu Plaza Chicago
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, (2125)
"Loved and enjoyed our stay"
United States
Luis
The price is 2.896.657 ₫
4.059.437 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Palmer House a Hilton Hotel
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 13 km from Woodlawn
7.8 out of 10, Good, (1025)
"Loved it will be back. "
United States
Antonio
The price is 2.248.237 ₫
2.639.200 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western River North Hotel
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (1744)
"Great staff with a great view of the city! Easy access to the L train to Wrigley Field. Will stay again!"
United States
Joseph
The price is 1.876.974 ₫
2.203.072 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
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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Where to stay in Woodlawn

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

Downtown Chicago

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop - Downtown featuring a river or creek

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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 which includes 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

Explore a world of travel with Expedia

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.
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.