Woodlawn Hotels, Chicago

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Check prices for these dates

Tonight
10 Nov - 11 Nov
Tomorrow
11 Nov - 12 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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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, (161 reviews)
"The motel smell like rats. And i stay there no more 30 minutes and chek out i pay $130"
United States
Rifki
The price is AU$140
includes taxes & fees
6 Dec - 7 Dec
Best Motel By OYO Chicago I-90
A modern hotel lobby with seating areas, a reception desk, and an elevator.

2. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 10.3 km from Woodlawn
8.2 out of 10, Very good, (2,751 reviews)
"Room was dated but clean, staff was friendly, location was perfect for my needs"
United States
Michelle
The price is AU$148
includes taxes & fees
7 Dec - 8 Dec
Best Western Grant Park Hotel
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

3. 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, (1,221 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is AU$181
includes taxes & fees
10 Dec - 11 Dec
Hilton Vacation Club Hotel Blake Chicago
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

4. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 10.6 km from Woodlawn
9.0 out of 10, Wonderful, (1,000 reviews)
"Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!"
United States
Taso
The price is AU$220
includes taxes & fees
7 Dec - 8 Dec
Le Méridien Essex Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

5. 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, (2,199 reviews)
"Great place to stay at"
United States
Aran
The price is AU$164
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Chicago Downtown South Loop
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

6. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 12.8 km from Woodlawn
8.8 out of 10, Excellent, (2,587 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is AU$168
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

7. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,584 reviews)
"Great hotel"
United States
Daniel Michael
The price is AU$276
includes taxes & fees
26 Nov - 27 Nov
Swissotel - Chicago
A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

8. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,536 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is AU$275
includes taxes & fees
22 Nov - 23 Nov
Hilton Chicago
A modern kitchen with a large window, a dining area, and a view of the sea.

9. 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, (2,536 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is AU$180
includes taxes & fees
23 Nov - 24 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

10. 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, (2,780 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is AU$275
includes taxes & fees
23 Nov - 24 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

11. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 12.8 km from Woodlawn
9.2 out of 10, Wonderful, (1,595 reviews)
"Great hotel"
United States
Tracy
The price is AU$176
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Chicago Downtown
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

12. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,161 reviews)
"Rooms were excellent, staff was helpful, and this short trip was easier to manage this close to our destination."
United States
Skylar
The price is AU$199
includes taxes & fees
22 Nov - 23 Nov
Congress Plaza Hotel
A luxurious bathroom with a large oval bathtub, a chandelier, and two large mirrors with floral arrangements.

13. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.6 km from Woodlawn
8.4 out of 10, Very good, (3,979 reviews)
"Friendly staff and great location"
United States
Alexis
The price is AU$140
includes taxes & fees
7 Dec - 8 Dec
The Whitehall Hotel, BW Premier Collection
A cozy room with a sofa, a dining table, and a window with a view of buildings.

14. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
11.7 km from Woodlawn
9.2 out of 10, Wonderful, (408 reviews)
"It was a fantastic stay!"
United States
Elzbieta
The price is AU$208
includes taxes & fees
11 Nov - 12 Nov
LIVN - West Loop Chicago
Restaurant

15. 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, (1,442 reviews)
"Will definitely stay again!!"
United States
Jasmine
The price is AU$218
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Chicago Central Loop
A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

16. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 12.9 km from Woodlawn
9.0 out of 10, Wonderful, (1,960 reviews)
"Hotel is great for the price."
United States
alex
The price is AU$147
includes taxes & fees
7 Dec - 8 Dec
ACME Hotel Chicago, Outset Collection by Hilton
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

17. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,339 reviews)
"The location is very convenient to go for restaurant, shopping and sightseeing."
Canada
Kenneth
The price is AU$183
includes taxes & fees
10 Dec - 11 Dec
Central Loop Hotel
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

18. 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, (5,063 reviews)
"Great place to stay"
United States
Melissa
The price is AU$175
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
A modern hotel lobby with a bar area, seating arrangements, and a television screen.

19. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 12.1 km from Woodlawn
8.8 out of 10, Excellent, (1,719 reviews)
"Great location, friendly staff, convenient parking"
United States
Lisa
The price is AU$183
includes taxes & fees
23 Nov - 24 Nov
Cambria Hotel Chicago Loop - Theatre District
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

20. 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, (3,902 reviews)
"Great Location"
United States
Natasha
The price is AU$290
includes taxes & fees
23 Nov - 24 Nov
LondonHouse Chicago, Curio Collection by Hilton
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

Compare popular hotels in Woodlawn

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A room with large windows, a wooden floor, and a built-in air conditioning unit.
Best Motel By OYO Chicago I-90
2.5 star property
3.4
161 reviews
View
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,780 reviews
View
A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.
Hilton Chicago
4.0 star property
8.6
Excellent
3,536 reviews
View
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago
4.0 star property
9.6
Exceptional
1,221 reviews
View
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,199 reviews
View

Our guide on 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

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

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

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

The hotel has been reburbished beautifully. Staff have been amazing letting us hang out in the lounge waiting for our train departure. Great location, fantastic cafe next door, great bars in the area. Only a short walk to Michigan Avenue for hop on hop off bus.
Australia
Cherrie
Reviewed October 12, 2024
Hilton Vacation Club Hotel Blake Chicago

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. 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.