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Check prices for these dates

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May

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Our top choices for Woodlawn hotels

Lobby

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.0 star property
Woodlawn
3.8 out of 10, (64 reviews)
"Parking"
United States
Sydney
The price is Rp1.398.669
Rp1.740.558 total
includes taxes & fees
3 May - 4 May
Best Motel By OYO Chicago I-90
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 11.7 km from Woodlawn
8.6 out of 10, Excellent, (2,393 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is Rp2.875.376
Rp3.848.462 total
includes taxes & fees
10 May - 11 May
Palmer House a Hilton Hotel
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, (2,445 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is Rp4.134.814
Rp5.501.455 total
includes taxes & fees
11 May - 12 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior detail

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 13.1 km from Woodlawn
8.6 out of 10, Excellent, (555 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is Rp1.454.962
Rp1.707.978 total
includes taxes & fees
27 Apr - 28 Apr
FOUND Hotel Chicago River North
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Woodlawn
8.0 out of 10, Very good, (2,883 reviews)
"Was nice! "
Canada
Emilie
The price is Rp1.414.311
Rp2.467.309 total
includes taxes & fees
21 Apr - 22 Apr
Freehand Chicago
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.2 km from Woodlawn
7.6 out of 10, Good, (1,301 reviews)
"Amazing stay "
United States
Napoleon
The price is Rp1.980.792
Rp2.325.389 total
includes taxes & fees
20 Apr - 21 Apr
The Chicago Hotel Collection - Magnificent Mile
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, (3,883 reviews)
"Great hotel "
United States
Marina
The price is Rp2.148.401
Rp3.006.543 total
includes taxes & fees
26 Apr - 27 Apr
Hotel Riu Plaza Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,142 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is Rp1.978.110
Rp2.322.242 total
includes taxes & fees
26 Apr - 27 Apr
Congress Plaza Hotel
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,188 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is Rp2.217.381
Rp2.603.446 total
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,091 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is Rp2.323.093
Rp2.727.241 total
includes taxes & fees
28 Apr - 29 Apr
River Hotel
55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.3 km from Woodlawn
9.6 out of 10, Exceptional, (3,929 reviews)
"Loved the stay here !"
United States
Alisha
The price is Rp2.485.272
Rp2.917.633 total
includes taxes & fees
26 Apr - 27 Apr
L7 Chicago by LOTTE
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,733 reviews)
"We love staying here "
United States
Carrie
The price is Rp3.420.611
Rp4.571.930 total
includes taxes & fees
8 May - 9 May
Hilton 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, (2,236 reviews)
"Great stay!"
United States
Jessica
The price is Rp2.049.788
Rp2.930.997 total
includes taxes & fees
26 Apr - 27 Apr
Silversmith Hotel Chicago Downtown
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 14.4 km from Woodlawn
8.2 out of 10, Very good, (1,374 reviews)
"Very beautiful place to stay"
United States
angie
The price is Rp2.250.900
Rp2.642.488 total
includes taxes & fees
27 Apr - 28 Apr
The Chicago Hotel Collection Ambassador Gold Coast
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 11.9 km from Woodlawn
9.4 out of 10, Exceptional, (1,044 reviews)
"Lots of places to eat and shop nearby"
United States
Analicia
The price is Rp2.305.045
Rp3.244.094 total
includes taxes & fees
10 May - 11 May
Staypineapple, An Iconic Hotel, The Loop
Lobby sitting area

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, (1,876 reviews)
"Great location and a very high class hotel."
United States
Cornelius
The price is Rp1.669.413
Rp1.993.229 total
includes taxes & fees
28 Apr - 29 Apr
Hotel Saint Clair- Magnificent Mile
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,083 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is Rp1.884.774
Rp2.212.740 total
includes taxes & fees
27 Apr - 28 Apr
Central Loop Hotel
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.1 km from Woodlawn
9.4 out of 10, Exceptional, (2,086 reviews)
"Great location and very clean hotel with nice staff. "
United States
Carrie
The price is Rp2.305.045
Rp3.218.984 total
includes taxes & fees
26 Apr - 27 Apr
Arlo Chicago
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,424 reviews)
"Great stay"
United States
Ashley
The price is Rp2.200.192
Rp2.582.959 total
includes taxes & fees
26 Apr - 27 Apr
Eurostars Magnificent Mile
Lobby sitting area

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, (2,188 reviews)
"Great stay!"
United States
Hannah
The price is Rp2.389.271
Rp2.805.245 total
includes taxes & fees
26 Apr - 27 Apr
Club Quarters Hotel Wacker at Michigan, Chicago
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. Learn more about Woodlawn
Learn more about Woodlawn

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

The Loop

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

Underground passage in the Chicago O'Hare airport

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

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.

Top Woodlawn Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Hotel is in a perfect spot if you want to be in the middle of everything. Room was nice and clean. Breakfast was fantastic! I didn't expect much but they have gone beyond what some hotels provide. Staff was great from check-in to check-out. I will definitely recommend this hotel to friends and family"
Christy 4-night trip
Posted 2 hours ago
Hotel Riu Plaza Chicago

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 50 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.