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Hotels in Woodlawn

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Top 10 Hotels in Woodlawn

Best Motel By OYO Chicago I-90

2.0 star property
3.2 out of 10, (33)
"Easy, safe parking "
The price is S$117
includes taxes & fees
9 Sept - 10 Sept
Best Motel By OYO Chicago I-90

Ameristar Casino Hotel East Chicago

4.0 star property
8.4 out of 10, Very good, (1011)
"Great place to visit and stay"
The price is S$173
includes taxes & fees
1 Sept - 2 Sept
Ameristar Casino Hotel East Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2073)
"Beautiful property, will definitely stay there again."
The price is S$284
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

4.5 star property
8.2 out of 10, Very good, (1173)
"Awesome place to stay"
The price is S$228
includes taxes & fees
1 Sept - 2 Sept
The Wade

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2583)
"Great experience with staff, room and overall stay! "
The price is S$277
includes taxes & fees
1 Sept - 2 Sept
Swissotel - Chicago

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1512)
"This is a nice hotel in a great neighborhood. "
The price is S$341
includes taxes & fees
2 Sept - 3 Sept
Loews Chicago Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1981)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is S$240
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Chicago - Magnificent Mile

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1610)
"Lovely hotel and in the most convenient location"
The price is S$330
includes taxes & fees
1 Sept - 2 Sept
Radisson Blu Aqua Hotel Chicago

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1844)
"Great Location - Great Room and Great Service - cannot ask for more. "
The price is S$444
includes taxes & fees
17 Aug - 18 Aug
Fairmont Chicago at Millennium Park

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2793)
"We love our stay here !"
The price is S$210
includes taxes & fees
24 Aug - 25 Aug
Aloft Chicago Mag Mile

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1010)
"Great location and hotel "
The price is S$223
includes taxes & fees
2 Sept - 3 Sept
Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (2023)
"Would stay here again!"
The price is S$187
includes taxes & fees
3 Sept - 4 Sept
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3326)
"Great location and wonderful hotel. "
The price is S$349
includes taxes & fees
24 Aug - 25 Aug
Hyatt Regency Chicago

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2619)
"Great location and hotel!"
The price is S$217
includes taxes & fees
24 Aug - 25 Aug
Hilton Chicago/Magnificent Mile Suites

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1938)
"Great stay"
The price is S$222
includes taxes & fees
24 Aug - 25 Aug
Millennium Knickerbocker Chicago

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1028)
"Best place we have stayed in Chicago in a long time. "
The price is S$278
includes taxes & fees
24 Aug - 25 Aug
Hyatt Centric Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1160)
"Enjoyed staying here!"
The price is S$218
includes taxes & fees
13 Aug - 14 Aug
The Chicago Hotel Collection - Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1693)
"We loved the price and location of this hotel. "
Hotel Saint Clair- Magnificent Mile

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2293)
"Beautiful hotel , breakfast was amazing "
The price is S$300
includes taxes & fees
2 Sept - 3 Sept
Hotel Riu Plaza Chicago

The Blackstone, Autograph Collection

4.0 star property
9.0 out of 10, Wonderful, (1002)
"Pleasant with great views and a good restaurant."
The price is S$335
includes taxes & fees
1 Sept - 2 Sept
The Blackstone, Autograph Collection
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.

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 map

Downtown Chicago

2 out of top 10 points of interest in this area

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 map

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 map

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 map

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.

Lincoln Park map

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top Woodlawn Hotel Reviews

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 43 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. 63rd Street Beach and Lorado Taft's Midway Studios 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?

Ready to get out and explore the city? Cottage Grove Station is the closest metro station. To venture out of town, take a train from Chicago 63rd Street Station.