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Our top choices for Woodlawn hotels

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 was easy. Just a sign in"
United States
David
The price is ฿2,254
฿2,805 total
includes taxes & fees
28 Apr - 29 Apr
Best Motel By OYO Chicago I-90

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, (2,473 reviews)
"Great place to stay "
United States
Mark
The price is ฿6,212
฿8,482 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,495 reviews)
"Clean, friendly, modern, overall great stay!!"
United States
Jennifer
The price is ฿6,922
฿9,378 total
includes taxes & fees
25 May - 26 May
Hyatt Regency Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,285 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is ฿6,379
฿8,718 total
includes taxes & fees
27 May - 28 May
Swissotel - Chicago

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,631 reviews)
"Great stay again. Great views. "
United States
JohNyra
The price is ฿6,925
฿9,368 total
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,977 reviews)
"Enjoyed the stay"
United States
Adam
The price is ฿5,054
฿6,917 total
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 12.7 km from Woodlawn
9.2 out of 10, Wonderful, (3,016 reviews)
"Great stay all around "
United States
Logan
The price is ฿6,825
฿9,242 total
includes taxes & fees
25 May - 26 May
InterContinental Chicago Magnificent Mile by IHG

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, (3,981 reviews)
"Great hotel, clean an super friendly staff.. would recommend"
United Kingdom
Joel
The price is ฿6,625
฿7,877 total
includes taxes & fees
24 May - 25 May
L7 Chicago by LOTTE

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (2,139 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is ฿5,544
฿7,726 total
includes taxes & fees
8 May - 9 May
Fairmont Chicago at Millennium Park

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.2 km from Woodlawn
8.6 out of 10, Excellent, (1,930 reviews)
"Nice hotel"
United States
Oliver
The price is ฿6,488
฿8,551 total
includes taxes & fees
25 May - 26 May
Radisson Blu Aqua Hotel Chicago

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.6 km from Woodlawn
9.4 out of 10, Exceptional, (2,423 reviews)
"Great stay! "
United States
Karen
The price is ฿7,695
฿10,094 total
includes taxes & fees
25 May - 26 May
Sofitel Chicago Magnificent Mile

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, (3,667 reviews)
"Loved staying at this hotel"
United States
Kimberly Marie
The price is ฿5,702
฿7,725 total
includes taxes & fees
10 May - 11 May
LondonHouse Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (2,758 reviews)
"Clean room and great location "
United States
Diana
The price is ฿5,119
฿7,032 total
includes taxes & fees
25 May - 26 May
Hilton Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,151 reviews)
"Great stay"
United States
Matthew
The price is ฿4,296
฿5,108 total
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,213 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is ฿4,797
฿5,632 total
includes taxes & fees
30 Apr - 1 May
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,141 reviews)
"Very convenient location, kind staff, and comfy rooms. "
United States
Molly Christina
The price is ฿4,625
฿5,499 total
includes taxes & fees
25 May - 26 May
River Hotel

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 11.6 km from Woodlawn
9.2 out of 10, Wonderful, (1,340 reviews)
"We really enjoyed our stay! The staff was incredibly pleasant, and the location was perfect—close to all attractions. Highly recommend!"
United States
Stephanie
The price is ฿5,261
฿6,255 total
includes taxes & fees
9 May - 10 May
Hilton Garden Inn Chicago Central Loop

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.7 km from Woodlawn
8.6 out of 10, Excellent, (2,447 reviews)
"Great stay!"
United States
Aaron Michael
The price is ฿4,482
฿5,328 total
includes taxes & fees
10 May - 11 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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, (2,244 reviews)
"Super nice staff, nice room, great location. We really enjoyed our stay. "
United States
Jim
The price is ฿3,839
฿5,548 total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown

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, (1,390 reviews)
"Great stay, love the surrounding area. Rooms a bit small but overall a great stay. "
United States
Eric
The price is ฿4,216
฿4,949 total
includes taxes & fees
28 Apr - 29 Apr
The Chicago Hotel Collection Ambassador Gold Coast
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.

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.

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

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

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.

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