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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, (2,472 reviews)
"Great place to stay "
United States
Mark
The price is ฿6,130
฿8,385 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2,414 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is ฿4,762
฿6,467 total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,137 reviews)
"Very convenient location, kind staff, and comfy rooms. "
United States
Molly Christina
The price is ฿3,804
฿4,523 total
includes taxes & fees
25 May - 26 May
River Hotel

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

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,147 reviews)
"Great stay"
United States
Matthew
The price is ฿4,296
฿5,108 total
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel

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, (2,137 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

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

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, (1,051 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is ฿4,282
฿6,034 total
includes taxes & fees
26 May - 27 May
Staypineapple, An Iconic Hotel, The Loop

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, (3,976 reviews)
"Great hotel, clean an super friendly staff.. would recommend"
United Kingdom
Joel
The price is ฿6,625
฿7,778 total
includes taxes & fees
30 Apr - 1 May
L7 Chicago by LOTTE

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (3,974 reviews)
"Enjoyed the stay"
United States
Adam
The price is ฿4,737
฿6,539 total
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza Chicago

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, (3,664 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, (2,757 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

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, (2,492 reviews)
"I love the stay definitely will be booking here next time"
United States
Ashley
The price is ฿5,050
฿6,810 total
includes taxes & fees
8 May - 9 May
Hyatt Centric The Loop Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (3,212 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is ฿3,896
฿4,573 total
includes taxes & fees
28 Apr - 29 Apr
Aloft Chicago Mag Mile

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

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 11.9 km from Woodlawn
8.6 out of 10, Excellent, (2,784 reviews)
"The hotel is good"
United States
Agnes
The price is ฿4,318
฿5,701 total
includes taxes & fees
10 May - 11 May
La Quinta Inn & Suites by Wyndham Chicago Downtown

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, (2,223 reviews)
"Perfect location great room for the price "
United States
Lisa
The price is ฿3,960
฿4,708 total
includes taxes & fees
25 May - 26 May
Club Quarters Hotel Wacker at Michigan, Chicago

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, (1,339 reviews)
"It was a great stay and good getaway "
United States
Ciara
The price is ฿3,295
฿3,869 total
includes taxes & fees
29 Apr - 30 Apr
The Chicago Hotel Collection - Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.6 km from Woodlawn
9.4 out of 10, Exceptional, (2,417 reviews)
"Great stay! "
United States
Karen
The price is ฿6,925
฿9,179 total
includes taxes & fees
25 May - 26 May
Sofitel Chicago Magnificent Mile
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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