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

Hotels in Woodlawn, Chicago

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2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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Our top choices for Woodlawn hotels

A room with large windows, a wooden floor, and a built-in air conditioning unit.

1. Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90
2.5 star property
Woodlawn
3.6 out of 10, (145 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is RM335
RM393 total
includes taxes & fees
11 Oct - 12 Oct
Best Motel By OYO Chicago I-90
A large, historic building with a central courtyard surrounded by trees.

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,285 reviews)
"Great stay!"
United States
Alan
The price is RM654
RM898 total
includes taxes & fees
24 Oct - 25 Oct
Hilton Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

3. 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, (2,718 reviews)
"Amazing place to stay"
United States
Shanequa
The price is RM1,292
RM1,676 total
includes taxes & fees
22 Oct - 23 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
A hotel lobby with a bar area, a chandelier, and a reception desk.

4. Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop
3.5 star property
Theatre District, 11.8 km from Woodlawn
9.4 out of 10, Exceptional, (1,002 reviews)
"We enjoyed our stay."
United States
Karla
The price is RM1,071
RM1,274 total
includes taxes & fees
24 Oct - 25 Oct
Residence Inn Chicago Downtown/Loop
A modern kitchen with a large window, a dining area, and a view of the sea.

5. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,482 reviews)
"Great overall stay within walking distance of so much."
United States
Cecilia
The price is RM852
RM1,013 total
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel room with a sofa, armchairs, a coffee table, a flat-screen TV, and a patterned wall.

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.1 km from Woodlawn
9.6 out of 10, Exceptional, (1,244 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is RM1,287
RM1,530 total
includes taxes & fees
14 Oct - 15 Oct
Hilton Vacation Club Hotel Blake Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

7. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 10.4 km from Woodlawn
8.8 out of 10, Excellent, (2,162 reviews)
"Great place to stay at"
United States
Aran
The price is RM762
RM906 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Chicago Downtown South Loop
An outdoor seating area with a glass table, orange cushions, and potted plants.

8. Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 12.4 km from Woodlawn
8.6 out of 10, Excellent, (1,836 reviews)
"Quick check in process, great location, helpful staff"
United States
Brandi
The price is RM1,278
RM1,664 total
includes taxes & fees
3 Oct - 4 Oct
Sheraton Grand Chicago Riverwalk
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

9. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,240 reviews)
"Easy check in, rooms were clean, convenient location."
United States
John
The price is RM654
RM778 total
includes taxes & fees
26 Oct - 27 Oct
Congress Plaza Hotel
A modern hotel with a glass facade, multiple floors, and a visible entrance.

10. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 12 km from Woodlawn
8.8 out of 10, Excellent, (1,629 reviews)
"Perfect location and great accommodations! Would stay again!"
United States
Lauren
The price is RM864
RM1,027 total
includes taxes & fees
25 Oct - 26 Oct
Hyatt Place Chicago/Downtown - The Loop
A modern hotel with a glass facade, multiple floors, and a prominent sign.

11. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
12.4 km from Woodlawn
9.2 out of 10, Wonderful, (1,004 reviews)
"Hotel was clean, the room was comfortable and spacious, the amenities were nice, and the breakfast was good. Would stay again."
United States
Rebecca
The price is RM922
RM1,096 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Chicago West Loop Fulton Market Area
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

12. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.6 km from Woodlawn
9.0 out of 10, Wonderful, (4,970 reviews)
"Very nice hotel, friendly staff, good location"
United States
Brian
The price is RM710
RM844 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Chicago/Magnificent Mile Suites
A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

13. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 11.7 km from Woodlawn
9.2 out of 10, Wonderful, (1,001 reviews)
"I loved the location, the breakfast, the comfortable bed and the proximity of public transportation."
United States
Jacqueline
The price is RM835
RM993 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Majestic Chicago Theatre District
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

14. 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, (4,887 reviews)
"Excelent location, Good service and Great Restaurant."
United States
GUILLERMO
The price is RM1,206
RM1,434 total
includes taxes & fees
1 Oct - 2 Oct
L7 Chicago by LOTTE
A grand lobby with a central bar, high ceilings, and classical architecture.

15. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.7 km from Woodlawn
8.6 out of 10, Excellent, (1,007 reviews)
"The hotel was absolutely stunning! Loved the convenience of it being right down town!"
United States
Amanda
The price is RM811
RM964 total
includes taxes & fees
23 Oct - 24 Oct
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A multi-story hotel with a prominent sign reading "Crowne Plaza."

16. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (2,673 reviews)
"Great stay, close to great food and ambiance in West Loop."
United States
Victoria
The price is RM713
RM848 total
includes taxes & fees
25 Oct - 26 Oct
Crowne Plaza Chicago West Loop by IHG
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

17. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 10.9 km from Woodlawn
7.8 out of 10, Good, (2,866 reviews)
"Great stay will be returning"
United States
Tremecka
The price is RM656
RM780 total
includes taxes & fees
25 Oct - 26 Oct
Travelodge by Wyndham Downtown Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

18. 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, (3,862 reviews)
"Great location! Would stay again!"
United States
Sharee
The price is RM1,025
RM1,340 total
includes taxes & fees
25 Oct - 26 Oct
LondonHouse Chicago, Curio Collection by Hilton
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

19. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
12.7 km from Woodlawn
9.0 out of 10, Wonderful, (1,307 reviews)
"A great hotel in a bustling area. We had a great stay."
United States
Joel
The price is RM1,071
RM1,274 total
includes taxes & fees
4 Oct - 5 Oct
Hyatt House Chicago/West Loop-Fulton Market
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

20. 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, (2,408 reviews)
"We enjoyed our stay; everything was nearby to walk. Staff was great super nice and we felt so welcomed."
United States
Carmen
The price is RM807
RM1,084 total
includes taxes & fees
25 Oct - 26 Oct
Silversmith Hotel 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.
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Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most.
A cityscape with tall skyscrapers and a historic tower.

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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

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

A river with yellow boats, a bridge, and tall buildings.

The Loop

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

A large, historic building with a central tower and multiple windows, located near a body of water.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Expedia said free breakfast. There was no free breakfast. 😞"
Leslie 1-night trip
Posted less than an hour ago
Fairmont Chicago at Millennium Park

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 49 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. Obama Presidential Center and 63rd Street Beach are also a couple of places to visit in the neighbourhood. Oak Woods Cemetery, Lorado Taft's Midway Studios and Stony Island Arts Bank 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 Rockefeller Memorial Chapel or Oriental Institute Museum.
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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