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

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9 Oct - 11 Oct
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16 Oct - 18 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
3.4 out of 10, (148 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is 2.138.006 ₫
2.509.807 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Best Motel By OYO Chicago I-90
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

2. 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, (3,863 reviews)
"Great location! Would stay again!"
United States
Sharee
The price is 5.965.623 ₫
7.865.590 ₫ total
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

3. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,504 reviews)
"Beautiful hotel in a great location!"
United States
Mercy
The price is 6.420.518 ₫
8.560.558 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A dining table set for six with a cityscape view through large windows.

4. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,546 reviews)
"Great stay"
United States
Hilary
The price is 4.971.352 ₫
6.825.949 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

5. 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, (1,226 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is 4.466.809 ₫
5.310.834 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

6. 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, (4,980 reviews)
"A fantastic A+ location in a well kept, boutique type hotel."
United States
Jeffrey Thomas
The price is 5.179.565 ₫
6.157.985 ₫ total
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE
A modern kitchen with a marble island, fruit bowls, and a city view.

7. 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, (2,313 reviews)
"Beautiful hotel and great location."
United States
Ruby
The price is 4.838.783 ₫
6.680.033 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

8. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13 km from Woodlawn
9.4 out of 10, Exceptional, (5,459 reviews)
"great location, room and breakfast is very good and various"
United States
Denys
The price is 4.170.038 ₫
5.698.587 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Hotel Riu Plaza Chicago
A room with two chairs and a small table, a large window with a city view at night.

9. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13.1 km from Woodlawn
9.0 out of 10, Wonderful, (3,946 reviews)
"Fantastic stay"
United States
Will
The price is 3.743.136 ₫
4.450.214 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Eurostars Magnificent Mile
The Intercontinental hotel facade with a large American flag and a floral display.

10. 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, (3,362 reviews)
"Great stay, perfect location would stay again"
United States
Kenan
The price is 5.510.728 ₫
7.461.495 ₫ total
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A dining area with a table set for four, large windows offering a cityscape view at dusk.

11. 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, (3,641 reviews)
"Perfect location and clean rooms"
United States
kelly
The price is 5.042.836 ₫
6.827.234 ₫ total
includes taxes & fees
3 Nov - 4 Nov
The Royal Sonesta Chicago Downtown
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

12. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 12.8 km from Woodlawn
9.2 out of 10, Wonderful, (1,919 reviews)
"Great breakfast, kind staff, clean room"
United States
Iminique
The price is 4.418.980 ₫
5.253.728 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago/River North
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

13. Hotel 505 River North

Hotel 505 River North
4.5 star property
River North, 12.8 km from Woodlawn
9.2 out of 10, Wonderful, (2,926 reviews)
"Loved our stay"
United States
Giana
The price is 5.952.626 ₫
7.909.302 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Hotel 505 River North
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

14. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 13 km from Woodlawn
8.6 out of 10, Excellent, (5,983 reviews)
"I’d stay here again."
United States
Eliana
The price is 4.396.885 ₫
5.227.456 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Embassy Suites by Hilton Chicago Downtown River North
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

15. The Wade

The Wade
4.5 star property
Streeterville, 12.9 km from Woodlawn
8.6 out of 10, Excellent, (2,127 reviews)
"Had a wonderful stay here"
United States
Erin
The price is 3.691.148 ₫
4.388.407 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Wade
An outdoor seating area with modern furniture and potted plants.

16. 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, (2,147 reviews)
"Loved the hotel!"
United States
Shannon
The price is 6.153.300 ₫
8.119.133 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Radisson Blu Aqua Hotel Chicago
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

17. 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, (2,422 reviews)
"Had a great trip, great location, helpful staff."
United States
Haesung
The price is 3.758.342 ₫
5.261.631 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Silversmith Hotel Chicago Downtown
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

18. 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, (2,707 reviews)
"Perfectly fine hotel super well situated"
United States
Sydney
The price is 4.949.258 ₫
6.656.973 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

19. River Hotel

River Hotel
4.0 star property
The Loop, 12.4 km from Woodlawn
8.8 out of 10, Excellent, (5,483 reviews)
"Great stay! Will definitely recommend to others visiting the city."
United States
Charlie
The price is 4.340.998 ₫
5.161.011 ₫ total
includes taxes & fees
1 Nov - 2 Nov
River Hotel
A modern building with a black facade and multiple windows. There is a sign for Hilton Garden Inn and a flagpole with flags.

20. Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk
3.0 star property
The Loop, 12.3 km from Woodlawn
9.0 out of 10, Wonderful, (2,181 reviews)
"Very nice and convenient hotel!"
United States
Nicole
The price is 4.241.701 ₫
5.042.957 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Chicago Downtown Riverwalk
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.
View all properties

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

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.

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

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.

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

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

River Hotel

River Hotel

10/10 Excellent
"Clean and very helpful staff. Great location!"
CASEY LASHEY 3-night trip
Posted 15 hours ago
River Hotel

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.
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. Obama Presidential Center 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.