A wooden bridge over a calm river, surrounded by lush greenery and a distant building.

Woodlawn Hotels, Chicago

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Our top choices for Woodlawn hotels

Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (89 reviews)
"This is not a good place."
United States
Dinesh Kumar
The price is AU$167
includes taxes & fees
8 July - 9 July
Best Motel By OYO Chicago I-90

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.1 km from Woodlawn
9.2 out of 10, Wonderful, (1,821 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is AU$270
includes taxes & fees
8 July - 9 July
Omni Chicago Hotel

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1,014 reviews)
"Great hotel to stay."
United States
Josias
The price is AU$367
includes taxes & fees
30 June - 1 July
theWit Chicago, a Hilton Hotel

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,414 reviews)
"The property was clean and the location was perfect!"
United States
Martha
The price is AU$269
includes taxes & fees
1 July - 2 July
Swissotel - Chicago

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, (1,635 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is AU$209
includes taxes & fees
1 July - 2 July
The Chicago Hotel Collection Ambassador Gold Coast

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,458 reviews)
"Staff was great."
United States
Marianne
The price is AU$383
includes taxes & fees
1 July - 2 July
Hyatt Regency Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,675 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is AU$258
includes taxes & fees
1 July - 2 July
Eurostars Magnificent Mile

River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,261 reviews)
"Excellent place to stay, as we found it central & walkable to most parks & attractions. The place was spotless & the staff were fantastic."
Canada
Jody
The price is AU$238
includes taxes & fees
5 July - 6 July
River Hotel

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, (3,757 reviews)
"Great location!"
United States
William
The price is AU$426
includes taxes & fees
30 June - 1 July
LondonHouse Chicago, Curio Collection by Hilton

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,167 reviews)
"Great stay!"
United States
Daniel
The price is AU$231
includes taxes & fees
29 June - 30 June
Congress Plaza Hotel

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, (1,109 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is AU$312
includes taxes & fees
1 July - 2 July
Staypineapple, An Iconic Hotel, The Loop

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 12.2 km from Woodlawn
9.0 out of 10, Wonderful, (1,419 reviews)
"The location is great and the rooms are comfortable and spacious. The free yoga classes were a nice bonus. It is clear that the hotel is going through a transition."
Canada
Caroline
The price is AU$356
includes taxes & fees
30 June - 1 July
Sports Illustrated Resorts Chicago

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, (2,496 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is AU$382
includes taxes & fees
6 July - 7 July
Palmer House a Hilton Hotel

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, (2,265 reviews)
"Wonderful stay"
United States
Taylor
The price is AU$251
includes taxes & fees
5 July - 6 July
Silversmith Hotel Chicago Downtown

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 13.3 km from Woodlawn
8.8 out of 10, Excellent, (2,283 reviews)
"Would definitely stay there again"
United States
Benjy
The price is AU$285
includes taxes & fees
1 July - 2 July
The Godfrey Hotel Chicago

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, (1,959 reviews)
"Beautiful hotel, amazing staff, perfect location. Will definitely make this a regular hotel to stay at while in Chicago."
United States
April
The price is AU$401
includes taxes & fees
7 July - 8 July
Radisson Blu Aqua Hotel 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, (1,689 reviews)
"Location was great"
United States
Pamela
The price is AU$423
includes taxes & fees
2 July - 3 July
Sheraton Grand Chicago Riverwalk

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 13 km from Woodlawn
8.8 out of 10, Excellent, (1,578 reviews)
"Great stay"
United States
Matt
The price is AU$282
includes taxes & fees
1 July - 2 July
Hotel 55 Chicago Downtown

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,192 reviews)
"Great hotel with awesome location"
United States
Daniel
The price is AU$251
includes taxes & fees
1 July - 2 July
Central Loop Hotel

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 12.4 km from Woodlawn
9.4 out of 10, Exceptional, (3,478 reviews)
"Incredible location, comfortable rooms, great bar and a restaurant attached! Loved staying here!"
United States
Feng
The price is AU$333
includes taxes & fees
1 July - 2 July
The Royal Sonesta Chicago Downtown
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.

Our guide on 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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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 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. 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?
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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