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

Hotels in Woodlawn

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Check prices for these dates

This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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, (155 reviews)
"A/c working, friendly staff, free parking but messy sheets and a baby mouse in the room"
United States
Saul
The price is S$124
includes taxes & fees
26 Oct - 27 Oct
Best Motel By OYO Chicago I-90
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 10.7 km from Woodlawn
8.6 out of 10, Excellent, (3,407 reviews)
"Friendly staff, great location"
Canada
Anna
The price is S$290
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A modern interior with a bar area, seating, and decorative wooden panels.

3. 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, (2,747 reviews)
"Excellent stay at a reasonably priced hotel. Will stay again!"
United States
Shelby Ryann
The price is S$190
includes taxes & fees
9 Nov - 10 Nov
Best Western Grant Park Hotel
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

4. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11 km from Woodlawn
8.0 out of 10, Very good, (10,166 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is S$177
includes taxes & fees
10 Nov - 11 Nov
Congress Plaza Hotel
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, (1,228 reviews)
"Great location. We walked to museum campus and millennial park."
United States
Kelsey
The price is S$262
includes taxes & fees
4 Nov - 5 Nov
Hilton Vacation Club Hotel Blake Chicago
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

6. 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, (1,002 reviews)
"Amazing location, super helpful staff, and clean/comfortable rooms. I stay here every time I am in town."
United States
Kayla Rene
The price is S$204
includes taxes & fees
11 Nov - 12 Nov
Le Méridien Essex 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, (2,190 reviews)
"Great place to stay at"
United States
Aran
The price is S$193
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chicago Downtown South Loop
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

8. 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, (2,902 reviews)
"Great stay"
United States
Sandra
The price is S$175
includes taxes & fees
12 Nov - 13 Nov
Travelodge by Wyndham Downtown 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, (2,515 reviews)
"Kids loved the pool, location was great for access to museums, and the breakfast was better than I expected!"
United States
Corinn
The price is S$219
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A dining table set for six with a cityscape view through large windows.

10. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
12.2 km from Woodlawn
9.0 out of 10, Wonderful, (3,568 reviews)
"Great stay"
United States
Hilary
The price is S$367
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
Lobby

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.7 km from Woodlawn
8.6 out of 10, Excellent, (2,725 reviews)
"Very Nice place to stay"
United States
Anand
The price is S$177
includes taxes & fees
2 Nov - 3 Nov
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

12. 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, (2,713 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is S$328
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
A snack bar with various packaged snacks and beverages.

13. 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, (1,717 reviews)
"Amazing location everything is close by"
United States
Vansh
The price is S$218
includes taxes & fees
1 Nov - 2 Nov
Cambria Hotel Chicago Loop - Theatre District
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

14. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.6 km from Woodlawn
8.6 out of 10, Excellent, (2,336 reviews)
"Great stay overall"
United States
Nathan
The price is S$183
includes taxes & fees
1 Nov - 2 Nov
Central Loop Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

15. 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, (2,590 reviews)
"Nice stay for the weekend."
United States
Poua
The price is S$211
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

16. 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, (2,728 reviews)
"Amazing place to stay"
United States
Shanequa
The price is S$350
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
The exterior of the Hampton Inn hotel with a prominent neon sign, a star logo, and a classic architectural design.

17. Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Hampton Inn Chicago Downtown/N Loop/Michigan Ave
3.0 star property
Theatre District, 12.3 km from Woodlawn
8.4 out of 10, Very good, (1,173 reviews)
"Staff friendly, hotel clean"
United States
Jeanvia
The price is S$196
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Chicago Downtown/N Loop/Michigan Ave
A bar area with a long counter, bar stools, and a mirrored wall.

18. 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, (3,978 reviews)
"Great stay"
United States
KURT
The price is S$181
includes taxes & fees
9 Nov - 10 Nov
The Whitehall Hotel, BW Premier Collection
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

19. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.3 km from Woodlawn
9.4 out of 10, Exceptional, (3,498 reviews)
"Beautiful hotel in a great location!"
United States
Mercy
The price is S$408
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

20. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
14.4 km from Woodlawn
9.0 out of 10, Wonderful, (1,450 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is S$217
includes taxes & fees
9 Nov - 10 Nov
Claridge House Chicago, Tapestry 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.
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Where to stay in Woodlawn

Find the best Woodlawn areas for the activities you enjoy most. Learn more about Woodlawn
Learn more about Woodlawn
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great location... Amazing hotel..."
katryna 2-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

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.

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